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[email protected] Letters in Organic Chemistry, 2013, 10, 693-714 693 1,2,4-Triazoles: A Review of Synthetic Approaches and the Biological Activity Suresh Maddila, Ramakanth Pagadala and Sreekanth B. Jonnalagadda* School of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, P. Bag X 54001, Durban 4000, South Africa Received May 21, 2013: Revised July 18, 2013: Accepted July 19, 2013 Abstract: 1,2,4-Triazoles and their derivatives have a distinct place in the field of medicinal and pharmaceutical chemistry. These are used as lead compounds for the synthesis of numerous heterocyclic compounds which possess diverse biological activities and play pivotal roles. This review covers the latest literature and knowledge on the synthetic procedures for various triazoles derivatives, their activities and pharmacological applications. Keywords: 1,2,4-Traizole, synthesis, biological activity, review. INTRODUCTION Heterocyclic chemistry is most challenging and amply rewarding field, and by far heterocycles are the largest class in organic chemistry. A majority of pharmaceuticals, biologically active agrochemicals, additives and modifiers used in industrial applications are heterocyclic by nature [1]. Synthetic organic chemists made significant progresses in discovering and developing wide range of heterocyclic compounds for the benefit of mankind. One remarkable structural feature and characteristic to heterocycles, which continue to be exploited, is their capability to accommodate the substituents around a central frame. Ever since their initial use in agriculture which began a century ago, the chemistry of nitrogen and sulfur containing heterocycles has made remarkable advances [2]. The pesticidal, fungicidal, antiviral and potential chemotherapeutic properties have been the inspiration for the overwhelming curiosity into the heterocyclic compounds in general, and the thiadiazoles, oxadiazoles, pyrazoles and triazoles in particular. Among the heterocyclic compounds, triazoles are one of the most key heterocycles exhibiting remarkable pharmacological activity as they are an essential constituent of all cells and living matter [3]. Triazole is a five-membered heterocyclic ring, which possesses three nitrogen atoms 1,2 and 4 positions. It is a much basic aromatic compound soluble in all organic solvents. The parent compound, triazole was synthesised for the first time by Fischer in 1878. Over 0.2 million 1,2,4-triazole derivatives have been reported in the literature and this class of organic compounds has become extraordinarily important due to their wide-ranging biological, agrochemical and chemical properties. The advances in the synthesis and biological activity of 1,2,4-triazoles from time to time have also been reviewed [4-8]. This review mainly aims at the recent advances in the field of synthesis and biological activity of 1,2,4-triaozles and their derivatives. *Address correspondence to this author at the School of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, P Bag X 54001, Durban 4000, SOUTH AFRICA; Tel: + 2731 260 7325 (Direct), 3090 (Secretary); Fax: + 2731 260 3091; E-mail:
[email protected]. 1875-6255/13 $58.00+.00 Triazoles form an important cluster among the heterocyclic compounds which possess a wide range of biological applications. While Pellizari et al. [9, 10] have reported the ability of 4-phenyl-1,2,4-triazoles to produce convulsions, indeed 1-phenyl-1,2,4-triazole was found to exhibit anticonvulsant property [11]. Benzimidazolyl-1,2,4-triazole acts as central nervous system depressant [12]. Besides these, the nitrofuryltriazoles (1) display potential urinary track antibacterial activity [13]. The -amino--phenyl-o-tolyl-1,2,4triazoles (2) were reported as sedative and anticonvulsant agents [14]. Apart from these, the 1,2,4-triazole derivatives possess important pharmacological activities such as antifungal and antiviral [15] properties. Examples of antifungal drugs are fluconazole (3) [16, 17], itraconazole (4) [18], ravuconazole (5) [19], voriconazole (6) [20-22] and posaconazole (7) [23]. Some triazole derivatives are considered as angiotensin II receptor antagonists [24-27]. Furthermore, various 1,2,4-triazole derivatives are reported as insecticides [28], antiasthmatics [29], anticonvulsants [30], antidepressants [31], anti-inflammatory [32], insecticidal [33] and plant growth regulators [34]. In addition, compounds having triazole moieties, such as vorozole (8), letrozole (9), and anastrozole (10) are found to be very effective aromatase inhibitors, which could prevent breast cancer [35-37]. 1,2,4-triazole moiety is reported to interact strongly with heme iron, and aromatic substituents on the triazole are very effective in interacting with the active site of aromatase [38, 39]. In fact, there are various drugs, which contain 1,2,4triazole nucleus viz., triazolam (11) [40], alprazolam (12) [41], etizolam (13) [42] and furacylin [43]. Many sulfur containing heterocycles are quite promising with several practical applications. The mercapto and thione substituted 1,2,4-triazole derivatives possess antibacterial [44-47], antifungal [48-50], antitubercular [51], antimycobacterial [52], anticancer [53, 54], diuretic [55, 56] and hypoglycemic [57] properties. © 2013 Bentham Science Publishers 694 Letters in Organic Chemistry, 2013, Vol. 10, No. 10 Maddila et al. N Me N N O 2N N N R2 Me NH2 N O N Cl R1 R3 X 1 2 F OH N N F N N N N 3 N O N N N O Cl O N N N O Me OH N N N CN N FS Me OH N NF F N N F 6 F 5 N Me 4 Cl N Me N O N N N O Cl N N N N OH Me O Me 7 Cl N N N N NC N Me N N N N Me Me N N N Cl 8 Cl Cl 9 Me Me CN 10 FROM HYDRAZONE DERIVATIVES R N HO O N N O RO O OH 14 R N N N S N ( ) N R' S N 17 Ar' NH2 R S 16 15 Ar R2 R1 O N N N N H N N N N N Me 20 CH2CH2OH N HO N CONH2 CONH2 Me N N S The formation of 1. which is used to reduce chronic iron overload in patients and other chronic anemias.2.4-triazole-3-carboxamide possesses antiviral activity against RNA and DNA viruses [58]. However. Maraviroc [63] (18) is known as an antiretroviral drug in the treatment of HIV infection.2. Deferasirox [64] (19) is a rationally-designed oral iron chelator. The acyl interchange between amide and hydrazide may complicate the reaction processes.2.4-triazoles.Triazole Derivatives Letters in Organic Chemistry. While.4-triazoles (16) reportedly exhibit potent antiviral activity against efavirenzand nevirapine-resistant viruses [61].2. OH N OH 19 HN N I. diarylthiazolotriazole (17) demonstrates selectivity against human COX-1 and COX-2 enzymes [62]. 10 H 3C N Cl N N N N N N Cl H 3C N N Cl N 13 12 11 Ribavirin (14). No. pyrazines and triazines exhibit diverse applications in the field of medicine. which proceed through acylhydrazidines as intermediates [69]. Isopropylidene ribavirin (15) acts as an inhibitor of several viruses [60]. N S N Cl solvent produced 1. pyridazines. Vol. The Pellizari reaction between hydrazides and amides at high temperature in the absence of O 695 18 N X . 10. O HO N N In addition to these. It inhibits the replication of HIV in human T lymphocytes [59]. The pyrazolo triazoles (20) are found to have analgesic activity [65]. the yield was found to be low due to the loss of amides through dehydration into the corresponding nitriles which do not participate in the Pellizari reaction.4-triazoline was first observed by Pinner [66-68] during the synthesis of amidrazones from an imidate and hydrazine. Trisubstituted 1. pyrimidines. triazoles fused with pyridines. a substituted 1. 2013. agriculture and industry. HCl + N HCONH2 Eqn. The amidrazone.4-triazoles. However.2.4-triazole. The Pellizari reaction of formamide with substituted hydrazine hydrochloride also gave N-substituted triazoles [75] (Eqn.5-dimethyl-1. 2).2. The fusion of Nformyl-N-alkyl/arylhydrazines with formamide at high temperature produced N-substituted triazoles [73. The treatment of arenenitrile with arenesulfonate of an aroylhydrazine afforded 3. The interaction of ethyl N-cyanoformimidate with benzimidazole-2-hydrazine in triethylamine gave the corresponding 5-aminotriazole [77. 10 Maddila et al. This method was extended to the reaction of arenenitriles with alkylhydrazide benzenesulfonates [84] (Eqn. On the other hand.4triazole was obtained [70] (Eqn. 1. 10. Contrary to this. there was an ambiguity of cyclization to oxadiazole or triazole. 2013.76]. 5).5-diaryltriazole [83]. The product formed was found to be 1-phenyl-3-ethyl-5-methyl-1. The conversion of amidrazone into triazole was effected in basic medium.5-dialkyl-1. However. 1). Similarly.696 Letters in Organic Chemistry. Vol. 6). However. Similarly.4-triazole [71.2. 72] (Eqn. 78].4-triazole or 4phenyl-1.2. whereas at high temperatures. 1 O H N H NH2 + Ph N H N N N i Ph N Ph (i) Eqn. the reaction of unsubstituted hydrazine with an amide derivative yielded amidrazone. However. 1-phenyl-3. while oxadiazole was obtained in the presence of an acid [82]. which on heating cyclized to triazole [81] (Eqn.75. 2 O H N H H N R + HCONH2 i R N N i RNHNH2.2. 4 ganic acid or in an acid-buffered solution or in the presence of pyridine hydrochloride produced 1. the reaction between cyanoacetylhydrazine or formylhydrazine and N.79]. 4). 3.2. the reaction failed with alkenenitriles and aroylhydrazine arenesulfonates. No.78.2. .4-triazoles were obtained in good yield by the treatment of alkylnitriles with zinc chloride complex of hydrazine at 140°C [85]. dehydration of amidrazone to triazole takes place in the presence of polyphosphoric acid.4-triazole was obtained by the reaction between N-formylbenzamide and phenylhydrazine [70. (Eqn.N-diphenylformamidine led to the formation of 3-cyanomethyl-4-phenyl-1. The Einhorn-Brunner reaction of hydrazine with diacylamines was exploited to get 1. Ph N N i Et Me N O O Et H N N H + Ph Me NH2 Ph N N ii Me Me N o o (i) 210 C (ii) >210 C Eqn.2. The treatment of hydrazine or its mono substituted derivatives with symmetrical or unsymmetrical diacylamines in an or- i N N N N H N Eqn. 3). 7).5-diphenyl-1. 3 (i) NH2 N N H H NHNH2 + EtO N CN (i) Et3N It was observed that acyl interchange did not occur when acetamide was heated with 1-phenyl-2-propionylhydrazine until the temperature was around 210°C. its reaction mechanism involving an amidrazone intermediate was later reported [80] (Eqn.4-triazoles [70. 74]. either on reaction with one more mole of amide derivative or self-condensation led to N2-(acetimidoyl)acetimidohydrazide. 2. Vol.2. 102] (Eqn.2. 10 2 1 R H N O NH2 + 3 R R O N H 1 R NH 1 R N N 3 R HN N 2 697 R 3 R O 2 R N Eqn.5-triphenyl-1.4triazole derivatives was the condensation of thiocarbohydrazides with aliphatic and aromatic carboxylic acids [98100] (Eqn.4triazole [89] (Eqn.2.2. 15).2.4-triazolium benzenesulfonate and 1-benzoyl-4-formamidobenzhydrazidine as the major products.2.4-triazole (Eqn.4. The later on reaction with hydrazine gave 4-amino-5-mercapto-3-substituted 1.4-triazoles were also prepared by fusing diformylhydrazine with amino phenols [97]. .4-triazole [91].N-dimethylformamide resulted in formation of 4-benzamido-3-phenyl-1. 12). 10.2.2. monosubstituted hydrazines and sodium hydrogencyanamide in the presence of 1-(3-dimethylaminopropyl)-3ethylcarbodiimide hydrochloride (EDC) [86] (Eqn.Triazole Derivatives Letters in Organic Chemistry.2.2.4-triazole [101. The reaction of latter compound with benzenesulfonic acid in N. 3-mercapto-4.4-triazole (Eqn. 9).4triazoles were prepared form the corresponding potassium dithiocarbazinates in the presence of pyrazinic acid hydrazide [90] (Eqn. 11).5-dimethyl-3-phenyl-1. which was further converted into its methyl ester with methyl iodide.4-triazoles [77]. Under similar conditions. the reaction of former compound with formic acid or acetic anhydride afforded 1methyl-3-phenyl. i PhSO3H + ArCN Ar N NH R Ar NH2 O (i) N R Eqn. Apart from these.and 1. 1. 95]. 13). However.2.5-disubstituted 1. The reaction of dibenzoylhydrazine with aniline in the presence of phosphorus pentoxide [92] or phenylphosphazoanilide [93] afforded 3. 88] (Eqn.2. pyrazinyl substituted 5-mercapto-1. 4-Substituted 1. The reaction of benzhydrazide benzenesulfonate with N. The aliphatic and aromatic diacylhydrazines upon treatment with ammonia gave 3.4-triazolium benzenesulfonate. Similarly. 8). 7 NH Ph N H H N Me O Me N N + Cl OEt HO N Ph Eqn.5-disubstituted 1.2. The treatment of Nsubstituted acetamides with oxalyl chloride generated imidoyl chlorides which on reaction with acylhydrazines followed by cyclization led to triazoles [96]. The treatment of acid hydrazide with carbon disulfide in the presence of potassium hydroxide gave potassium salt of 2acyldithiocarbazic acid. 6 N NH O R N H NH2.5-diamine derivatives were produced in one-pot reaction from the corresponding isothiocyanates.H2O (ii) N NH R N R Eqn.N-dimethylformamide gave 1. in which diformylhydrazine was initially formed [94. a mixture of hydrazine.4-triazole. Similarly. Alkaline hydrolysis of triazolium derivative produced 4-benzamido-3-phenyl-1. 5 NH R NH NH i X R N H NH2 + R HN NH ii R R X NH HN ii (i) N2H4 . ethanolic potassium hydroxide solution of thiophene carbohydrazide with carbon disulfide yielded the corresponding dithiocarbazate. ammonia and formaldehyde yielded 1.4-triazoles were obtained by the interaction between aryloxyacetic acid hydrazides and aryl isothiocyanates [87.4-triazoles. 2013. 8 Cyclization of N-benzimidoyl-N-methylhydrazine with ethyl chloroformate led to 5-hydroxy-1-methyl-3-phenyl1.4-Triazole-3. 10). 14). respectively [85].2. which subse- quently reacted with hydrazine to give 4-amino-5-mercapto3-(2-thienyl)-1. One of the choicest methods for the preparation of 1. No. 4-triazoles were also prepared by the reaction of S-methyl-N-arylisothiouronium iodide with substituted hydrazides [103] (Eqn.H2O Eqn. The reaction of N-acetyl-N. N N i 1 NH2 + R NCS 1 R HN R2 N N + R1 HN NH2 N NH2 N (i) NaNHCN / EDC Eqn.698 Letters in Organic Chemistry. an efficient mi- . 2013. 16). 10 R2 H N 2 R Maddila et al. On the other hand. Vol.2. 9 O O N N NCS NHNH2 R O i + R' SH N R R' (i) aq.N-dimethylhydrazonoformamide with primary . NaOH Eqn.4-triazoles. 11 N N O Ar O Ar H N N H S.5-disubstituted 1. 15 amines followed by acid catalyzed cyclization resulted in substituted 1. The former compound was generated in situ from acid hydrazide and N. 10.2. PhSO H 3 N NHCOPh ii N N Ph i NNHCHO H N Ph N H ii N NHCOPh Ph O Eqn. 10 O R N H i NH2 + CS2 + KOH HN N N NH R OS ii SCH3 SH N NH2 R (i) MeI (ii) N2H4. 12 NH Ph N N i Ph Ph OO Ph N Ph Eqn.N-dimethylformamide dimethyl acetal [104]. No. 13 (i) PhN=PNHPh S H2N N N H H (i) RCOOH / NH2 N N i R SH N NH2 Eqn. PhSO3H +(Me)2NCHO (i) PhSO3H (ii) NaOH The 3. 14 N N Ph O Ph N H NH2 .K + O SH N HN i O S N N (i) Pyrazinic acid hydrazide / water / HN PhNH2 + Eqn. 5-Disubstituted 1. 18 N C H R (i) 2CuCl2 / DMF / CH3 Eqn. 19).5-disubstituted 4-amino-1. 141].4-triazole was obtained from aliphatic nitrile and hydrazine [107] (Eqn. 26). II. triethylamine [148] or by their fusion [149].3. 10 N NH S Me NH R N H NH2 N + R' O OMe N H N NH2 + (i) CH2Cl2 / R' Eqn. 21). 17 crowave assisted one-pot and three-component synthesis of 1.2. 20). 18).4-triazoles by basecatalyzed condensation of nitriles and hydrazides under mi- The literature survey reveals that the cyclization of substituted thiosemicarbazides can occur in the presence of sodium carbonate [98.2. 10. 16 N N O i N H OMe N ii N N R (ii) RNH2 / AcOH / MW crowave irradiation (Eqn. [124] described an efficient one-step procedure. [125] have reported a new antifungal 1. Microwave irradiation has become a widely used method to rapidly synthesize many useful organic molecules with good yield and high selectivity [110-120].HI O R 699 i N N N R Eqn. 24).4-triazoles from aromatic nitriles and NH2NH2·2HCl in the presence of excess NH2NH2·2H2O in ethylene glycol under microwave irradiation (Eqn. 22).2.2.5-disubstituted 4amino-1. 17).2. 23). 25).4-triazole derivatives from substituted hydrazide using various solid supports under microwave irradiation.4-triazole by the reaction between phenylhydrazine and benzonitrile in the presence of sodium proceeded through amidrazone as probable intermediate [108]. H2O N H Eqn. 151] (Eqn. Dialkylamino-1. this reaction resembles the formation of 1-phenyl-3-hydroxy1. 2013.3-cycloaddition methodology between different nitriles and 1-(chloroalkyl)azo salts in the presence of SbCl5 as a Lewis acid [126-129]. The bis(1. FROM SEMICARBAZONE DERIVATIVES The ring closure of acyl derivatives of semicarbazides. In fact.2.4-triazoles were also obtained by treating nitriles with zinc hydrazine complexes [106].2.2.2. 19 .2.5triphenyl-1. In this case the product was found to be thiadiazole derivative instead of triazole [152.4Triazoles were also obtained by oxidative intramolecular cyclization of heterocyclic hydrazones with copper (II) chloride [109] (Eqn. the synthesis of 3. However.2. Triazoles were also afforded by the cyclization of S-alkylthiosemicarbazides in the presence of acetic anhydride [133] (Eqn. HN NH i RCN R N N R R N NH2 R HN NH (i) N2H4.4-triazoles was also reported from substituted primary amines [123]. Symmetrical 3. Bentiss et al. An efficient microwave-assisted one-pot and three-component synthesis of substituted 1. Kidwai et al.N-dimethylformamide dimethyl acetal and primary amine in the presence of acetic acid [105] (Eqn. 3. Vol.4-triazoles were prepared from aromatic aldehydes via nitriles by two-step reaction under microwave irradiation with no need to separate the intermediate [122] (Eqn.4-disubstituted thiosemicarbazides in acidic medium has also been a concept.4-triazolyl) derivatives were prepared by the base catalzsed cyclodehydration of bis(thiosemicarbazide) derivatives [150. The formation of 1.137-139]. which attracted overwhelming interest.2. Yeung et al.4-triazoles was accomplished by the reaction of acid hydrazide with N.2.2. Several potentially bioactive 1.Triazole Derivatives Letters in Organic Chemistry.5-disubstituted 1. N NH NH . 1. No.4-triazoles [130-132] (Eqn.4-triazole derivatives were prepared adopting 1.4-triazole from 1-phenylsemicarbazide in the presence of triethoxymethane [134-136] (Eqn. [121] have reported 3. alkoxides [140. the cyclization of 1. sodium hydroxide [142-147]. thiosemicarbazides or aminoguanidines in alkaline solution was one of the widely applied methods for the preparation of 1. H2O / MW H H N N i ArCHO Eqn. thiosemicarbazide on treatment with benzoyl chloride in boiling pyridine or alkali undergoes in situ benzoylation and cyclization.and trifluoroacetic acids [157].2. its reaction with 1-benzylidene-4-methylthiosemi-carbazone at 115°C in ace- S N R ( )n N S R Eqn.4-triazoline-5-thione derivatives with reasonable yield. 29). 10. The reaction of terephthalic acid hydrazide with phenyl/benzyl isothiocyanate gave the corresponding bis(thiosemicarbazide). 28). 21 O 1 R NH2 N H HN N i 2 R CN + 1 R R2 N (i) K2CO3 / BuOH / MW O H2N H N N H (i) OH Eqn. Herbst and Klingbeil [159] observed that the treatment of 1-acetyl-4-phenyl. On the other hand.thiosemicarbazide with lead oxide resulted in the formation of 3-methyl-4-phenyl-1. 26 tic acid gave 4-methyl-3-phenyl-1. Thermal [155] and acetic anhydride [145] catalyzed reactions of 4-alkyl/aryl-1-oxamoyl/carbamoylthiosemicarbazides were known to give 1.2HCl / NH2NH2.5-dihydro-1.4-triazoline-5-thione [154] (Eqn.700 Letters in Organic Chemistry. 25 (i) HCO2H S RHN (i) OH N H - H N H N ( )n O O S N H N NH HN N i NHR 153]. (Eqn. N N i ArCN Ar Ar N NH2 (i) Ethylene glycol / NH2NH2.2.H2O / MW Eqn. These reactions were also carried out with sulfur monochloride. 23 N Me N H N S NH N N i N H S MeS S Me N (i) Ac2O Eqn.2HCl / NH2NH2.2. 24 O N H H 2N H N Ph i N N Ph OH N Eqn.4-triazoles [158] (Eqn. Vol.2. 27). 10 Maddila et al.4- . resulting in the formation of 4-benzoyl-3-phenyl-1. 22 N N i N Ph HO - Ph N Ph Ph Eqn. No.4-triazoline-5-thione [156].2. which in the presence of NaOH was cyclized to bis 1.4-triazole-5-(1H)thiones were produced by treating 4-substituted thiosemicarbazides with di.HCl / Ar N NH2 O / MW N Me (ii) Ethylene glycol / NH2NH2. 2013. Apparently. 20 ii ArCN Ar N N Ar Ar N N (i) NH2OH. The 3-fluoroalkyl-4.2. or naphthylthiosemicarbazides with sodium hydroxide afforded 1. depending on the reaction conditions. 31).4-dichlorobenzoyl)-thiosemicarbazide resulted in 3(2. acetic and triflouroacetic acids [98.2.2.4-triazoline-5thiones were formed. 32). 2013. with hot acetic anhydride and acetic acid R N SH Eqn.4-triazole-5-thiol (Eqn.4-triazole-3-thiones [160-174]. Interestingly. On the other hand. Goswami et al. [176] reported that the oxidative cyclization of 1-(2. 30). pH>7 R 701 N H Eqn.4-bis(phenyl)1. H2SO4 gave 3-benzamido-5-hydroxy-1. Extension of this approach to substituted ethyl imidate hydrochloride in the presence of hydrazine yielded 3-alkyl/aryl-1. which in alkaline medium were cyclized to 2.4-dichlorophenyl)-1H-1. (Eqn.4-triazoline derivatives. Thus. The reaction of carboxylic acid chlorides with thiosemicarbazide gave acylthiosemicarbazides. Cyclization of morpholinoacetyl. 30 mixture. It was observed that initially formed 1(N-arylamidino)-4-alkylthiosemicarbazide underwent in situ cyclization by the attack of alkyl substituted nitrogen on arylamidino carbon followed by the elimination of ammonia [185].4-triazoline-5thiones [181]. Upon heating 4-alkylthiosemicarbazides with arylcyanamides.2. No.Triazole Derivatives Letters in Organic Chemistry.2. 34). Subsequently. oxidative cyclization of substituted aldehyde thiosemicarbazones induced by different metallic salts afforded 1.4triazoline-5-thione [177]. 27 HN N H N CF3 S N O CF3 R (i) Eqn. 4-alkyl-3-arylamino-1. 10 HN N S H 2N N H i NH2 + PhCOCl S O S N H N H NH2 i + CF3COOH S R N H Ph N Ph (i) Pyridine or NaOH. 28 O O O O + Ar i N C S N NH HN NHAr SNa NaS O O ii N ArHN H2N NH2 NH HN iii NH HN NH HS HN NHAr ArHN S N N N N N N Ar Ar S (i) NaH/DMF (ii) H+ (iii) NaOH Eqn.182-184].179].4-triazole was obtained [178] (Eqn.2. when treated with 20% NaOH yielded 5mercapto-3-phenyl-1.4-dihydro-3H-1. 10. The reactions involving alkyl imidates also proceeded in a like-wise manner.4-triazo- . The reaction of benzothiozolyl hydrazide with ammonium thiocyanate in boiling hydrochloric acid produced 1-(2benzothiazolylcarbonyl)thiosemicarbazide and the latter compound in the presence of sodium hydroxide underwent intramolecular cyclization to 3-(2-benzothiazolyl)-1.2. 33).2. The triazoles were also prepared by treating acid halides with lead (II) thiocyanate and hydrazine hydrate [175] (Eqn. whereas in the presence of conc.2. treatment of 4phenylthiosemicarbazide with ethylphenyl imidate hydrochloride at pH > 7 led to the formation of 3. Vol. 3-benzamido-5-methyl-1. the cyclization of 4-benzoyl-1-carbamoyl3-thiosemicarbazide resulted differently with substituted 1.4-triazoline-5-thione [180] (Eqn. 29 O HN N i R SH X (i) Pb(SCN)2 / N2H4.2. The former.4-triazole derivatives. On the other hand. Similar results were reported in the cyclocondensation of substituted thiosemicarbazides with formic. the reaction of 4-alkyl/ arylthiosemicarbazides with cyanamide in the presence of acid produced 3-amino-4-alkyl/aryl-5-mercapto-1.4-triazole.2.4-triazole.4-triazoles [144.H2O triazoline-5-thione.2.2.2. No.4- .2.4-triazol-5yl)alkanes were prepared by the base induced cyclization of corresponding bis(4-arylthiosemicarbazido)alkanes [191193] (Eqn.702 Letters in Organic Chemistry. the reaction of 4-(2-methylallyl)-2-phenylthiosemicarbazides with ketones afforded 3.4-diethoxycarbonylthiosemicarbazide under alkaline conditions [188] (Eqn. oxidation of Smethylthiosemicarbazone of benzaldehyde with hydrogen peroxide yielded 3-phenyl-5-methylthio-1. the 4phenylthiosemicarbazide gave 2-phenylamino-1. in addition to 4-phenyl-1.4triazole only.2. it was observed that the substituents in the 4position of thiosemicarbazide play a major role.2.4triazoline-5-thione from 1. aldehyde semicarbazones on heating in an alcoholic solution of ferric chloride led to the formation of 1.4-triazolidine-5-thiones [187]. Thus.4-thiadiazoles. While the treatment of 4-methylthiosemicarbazide with phenyl isocyanide produced only 4-methyl-1. Kurzer et al.2. Analogously.2. 1amidino-4-alkyl/arylthiosemicarbazide either by the attack of sulfur or nitrogen atom carrying alkyl/aryl substituent [186] (Eqn.HCl Ph (i) pH>7 les and 2-alkyl/arylamino-5-amino-1. 10. described the formation of 3-hydroxy-1.4-triazoline-5-thione. The formation of these products was explained by the nucleophilic displacement of ammonia from the intermediate. 2013. 32 N NH i H 2N S N H S HO OS NHCOPh N HN N iii H3C NHCOPh N (i) 20% NaOH (ii) conc.2. bis(4-aryl-3-thio-1. H2SO4 (iii) Ac2O / AcOH S Ph N H HN N EtO N H NH2 + Eqn. 34 During the reaction of thiosemicarbazide with phenyl isocyanide.4-triazoline-5-thione [190] (Eqn.2. Furthermore. 38). The oxidation of S-alkylthiosemicarbazones with H2O2 or FeCl3 also gave triazoles.3. The reaction of phenylhydrazine with potassium thiocyanate produced phenylthiosemicarbazide.4-triazoline-5thione [189].3-dimethyl-4-(2-methylallyl)-1-phenyl-1. Among different methods employed for the synthesis of triazoles. 33 NH. 31 NH2 S O S O ii N NH N (i) HCl / (ii) NaOH / Ph HN NH SH N HN N ii NHCOPh Eqn. 35). 39). the reaction of acylthiosemicarbazide with sodium methoxide [95] or sodium carbonate [138] resulted in 3-alkyl-5-mercapto-1.4thiadiazole. 37). Similarly. An acylation of latter by benzoyl chloride followed by cyclization gave 1. NH2 N N i Cl S SH N H Cl (i) NaOH NH NH2 N S HN NH N i + NH4SCN Eqn. 10 O N H Cl H N Cl Maddila et al.4-disubstituted thiosemicarbazides with carbonyl compounds (Eqn. Vol.4-triazole [194]. 36). considerable attention was devoted to the cyclocondensation of 2. i S N Ph Ph Eqn.3. On the other hand.2.2. 4.4triazole derivatives along with 1. 36 H N OEt HN N i S - N H OH N H O Eqn. On the other hand. 37 S Ph NH2 NH2 N H HN N N N i + PhHN S S N Ph (i) PhNC CONHNHCSNHR (CH2)n ( )n S CONHNHCSNHR (i) OH N NH HN N i Eqn.2. . However.4-triazolines [196] (Eqn. 10 703 N N HS S S RHN N H H N i NH2. cyclocondensation of 1-benzoylsemicarbazide and 1-isonicotinylsemicarbazide with primary amines in the presence of anhydrous zinc chloride gave 3. 43). 38 N N R R S - Eqn. Vol. 10. oxidation of 4benzylthiosemicarbazones with Br2/CHCl3 gave 1.HCl N N NH RHN S NH (i) Cl NH2 / NH2 Eqn.4-triazoles [197].Triazole Derivatives Letters in Organic Chemistry. No. 42).5-trisubstituted 1. 41).2.4-thiadiazoles in minor amounts.4-triazole [199] (Eqn. 40 triazoles.3.5-diamino1-thiocarbamoyl-1. 2013. a treatment with bromine in acetic acid resulted in exclusively 3-mercapto-1.4-triazoles [200] (Eqn.2. 39 O H 2N N H N R N N ii N N NH2 O O (i) alc. Interestingly. 35 R S 1 R N H N R 2 N NH i NH2 S N R1 3 2 R R 3 (i) R COR / H2SO4 O EtO S N H (i) OH N H Eqn. The reaction of 2-methyl-4-phenylthiosemicarbazides with cupric perchlorate in methanol gave 1.2. 44). 40). The treatment of hydrazide derivative of pyrrolyl ester with phenyl isothiocyanate followed by cyclization of the resulting semicarbazide derivative produced 1.4-triazole [198] (Eqn.HCl RHN N H N R NH2. The latter compounds were also obtained by the treatment of aldehydes and azodicarbamides with ferrous chloride [195] (Eqn.2.2. The reaction of thiosemicarbazide with Ncyanoguanidine in an acidic medium afforded 3. FeCl3 (ii) FeCl2 H2N i + RCHO HO N H R Eqn. Me S R N N H N N Ar N i S S H 2N R H 2N NH2 N H Ar N Me (i) Cu(ClO4)2 / MeOH + H N RN Eqn. A . 10.4triazoles [204] (Eqn. 49). Vol.3. MISCELLANEOUS METHODS The Chichibabin amidation of azines led to 3. 44 N N N N i Ar NHR1 R1 (i) R1 NH2 / an. The condensation of substituted amidrazones with maleic anhydride yielded 1.4-oxadiazoles on heating with hydrazine hydrate led to the corresponding 3.2. followed by the ring closure and loss of other atom.4-oxadiazoles into 1. The transformations of 4.2. The reaction of 1.4diaminotriazoles [208-210]. 10 Maddila et al.5-oxadiazole [203] (Eqn. 47).3.3. 48). 50) Similarly.2. the recyclization of 2-amino-1. The reaction of 3-aminofurazan-4-amidrazone with cyanogen bromide resulted in bicyclic 1.5diaryltriazoles [201].4oxadiazoles with ammonia and methylamine afforded respective triazoles in good yield [207].4oxadiazoles and bis-1.4-triazines to triazoles proceeded through amidrazone intermediates.6-dihydrazinopyrimidine hydrazines formed from haloaminopyridazine [202] and 1. ZnCl2 Ar N HN N Ar Ar H2N NH2 (i) NaNH2 III. The conversion of 1. No. 45).704 Letters in Organic Chemistry. 42 CONHNH2 i N N N S N ii N N N Ph NH N CONHNHCSNHPh Ph N N N Ph Ph Eqn.4-triazole derivatives was carried out with substituted anilines or aromatic diamines in the presence of trifluoroacetic acid.3.4-triazolyl1. The conversion of a non-triazole ring system into a triazole usually included the substitution of nitrogen for another heteroatom in a five-membered ring. with bisamidrazone as an intermediate (Eqn. 45 The cyclization of N-alkyl or aryl-N-guanidinothioureas or guanidinodithiocarbamic acids to mercaptotriazole amines was effected in the presence of alkali [206] (Eqn. The use of six membered ring systems as a source of amidrazones for synthesis of triazoles was scarcely reported. (Eqn. Ar N Ar Eqn. Triazoles were also obtained by the reaction between phydroxy phenylbiguanide and hydrazine [205] (Eqn. This process involved nucleophilic ring opening of the heterocycle. 2013. 43 (i) PhCNS / EtOH (ii) KOH / EtOH HN NH R OO N N i NH2 R Eqn.2. 41 H N H2N N NR H N NH S N H NH2 S NH2 N N H 2N NHR N Eqn.2. 46). H2O S R N NH H N NH NH HO NH2 H N N N i NH2 HS N R NH NH2 Eqn.4-dihydro-1.5-diaryl-1.3.5-tetrazines in the presence of conc.4-diaryl-1. The rearrangement of 1.2.2. 3.4-oxadiazoles in the presence of methylamine or propylamine on irradiation in methanol or acetonitrile led to the corresponding fluorinated 1-methyl or 1-propyl-1.4-thiadiazole were rearranged to triazolinethione in the presence of methylamine or hydrazine [213] (Eqn. No.5-diaryl-1.Triazole Derivatives Letters in Organic Chemistry. On the other hand.4-triazoles were formed [214]. 51).2.4-thiadiazoles to triazoles was similar to that of oxa analogs.4triazoles [214. 50 R' F15C7 N R' R' N N i O F15C7 N ii NO + OO F15C7 N OH NHR" R' N F15C7 (i) hv. 10.2. 46 NNH2 R NH2 N N + 705 1 R O O COOH N 2 R (i) Eqn.2.3. 52).2. The fluorinated 1. but the former were less reliable.4-triazoles [212] (Eqn.2-dihydro-1. employing the reducing agents such as zinc and acetic acid or sodium alkoxides. partly because they require higher temperatures below which by-products were favored.4. 2013. 48 (i) N2H4. 51 1. HCl gave 4-amino-3.6-diaryl-1.4. Isomerization of 3. 254 nm (ii) R"NH2 similar reaction has also transpired with aniline hydrochloride in pyridine [211]. 10 NNH2 H2N N NH NH2 H2N i N O (i) BrCN / KHCO3 N 1 2 O N N i O NHR N Eqn. 47 H N H N N H N H i NH2 N HO Eqn. In contrast to this.215]. 1. 49 (i) NaOH N i CF3 CF3 O N ii N NH iii F 3C H 2N O N N F 3C NH F3C N F3C CF3 N N N CF3 iii F3C MeHN NHMe N Me (i) NH3 (ii) MeNH2 (iii) P2O5 CF3 Eqn. 2-methylamino- N N R" Eqn.5-tetrazines under the influence of sodium ethoxide were isomerized to 1-aryl-3- . Thus. Vol. 3-dipolar cycloaddition between nitrile imines and the cyano group of activated nitriles produced 1-aryl-3. No.2. The potassium dithiocarbazate of acid hydrazides upon refluxing in acetic acid got cyclized to thiadiazoles. a substituted thiadi- . 219] first prepared an intermediate from hydrazonyl chlorides and primary amines in the presence of Et3N. when phenacylsulfonylacetic acid methyl ester was treated with hydrazine hydrate.706 Letters in Organic Chemistry. 52 Ar Ar N N N N i ArHN N N N Ar (i) NaOEt Eqn.4triazoles (Eqn.2. The nitrile imines were generated in situ from the corresponding hydrazonoyl chlorides in aq. 2013. 54 R Cl CO2Me N i R .2. 55 R2 NNHR2 1 R Cl + 3 R CN (i) Yb(OTf)3 arylamino-1. N N N NH i NHMe S S N Me o (i) MeNH2 / 160 C Eqn.2. 56).2. Buzykin et al. In an alternative two-step approach.5-trisubstituted 1.4-triazoles was reported via 1.3. sulfonylacetic acid via acid hydrazide.2.4-triazoles.5Trisubstituted 1.+ N N C CO2Me ii N N R1 R N CO2Me 1 (i) aq. Acid catalyzed hydrolysis of the former compounds led to oxadiazoles.5-disubstituted 1. Intriguingly. base induced cyclization of potassium dithiocarbazate with hydrazine hydrate afforded triazoles [222.4-triazoles Using Common Intermediates The synthesis of thiadiazoles. 10. 56 triles in the presence of ytterbium triflate as catalyst [221] (Eqn. The methyl ester of phenacylsulfonylacetic acid and benzylsulfonylacetic acid on treatment with hydrazine hydrate in the presence of pyridine gave the corresponding acid hydrazides. An improved method for synthesis of 1. oxadiazoles and triazoles was accomplished from a common intermediate. 55). 223] (Eqn.4-triazole by the rupture of nitrogen-nitrogen bond [216] (Eqn. which was then treated with a solution of 30% H2O2 and aqueous KOH to get 1. 53). [218. NaHCO3 / THAC (ii) R CN Eqn. 1.4-triazoles were also synthesized by the intermolecular cyclization of hydrazonyl chlorides with ni- N N i 1 R N 3 R Eqn. The 1. 53 R1 N NHR1 N N i R Ph Cl ii N NHR1 R2 N iii R NH (i) R2CN / Ag2CO3 / Et3N (ii) R2CH2NH2 / Et3N / MeCN (iii) H2O2 / KOH / MeCN H N R2 Eqn. 57). generated in situ from alkyl substituted 1chloroethylidene-2-alkylhydrazines in the presence of Ag2CO3 and Et3N [217]. NaHCO3 in the presence of tetrahexylammonium chloride (THAC) [220] (Eqn. 54). Vol.3-dipolar cycloaddition of nitrile imines.5-disubstituted-3-phenyl-1. Synthesis of 1. On the other hand. 10 Maddila et al.3. Triazole Derivatives Letters in Organic Chemistry.H2O O O O S NOH O O R R NOH O O N S O OMe i i H N S ii OMe O O R O S O NHNH2 iii O NOH O O S O .H2O / Pyridine / MeOH (ii) CS2 / KOH / EtOH (iii) H+ Eqn.H2O / Pyridine / EtOH (ii) NH2OH.+ NHNHCSK S R v iv NOH O S O S R O S S N N N NH2 vii O N N S R SH O R vii O NOH O N N vi O SH R O S O NOH O SH S R vii N NH2 SH N N O O N N O O S O SH N N O SH R (i) N2H4. 2013. 10. 58 707 . No. Vol.H2O (vi) H+ (vii) â -CD / H2O Eqn.HCl / EtOH (iii) CS2 / KOH / (iv) AcOH (v) N2H4. 10 R R O O O S ( )n i O O O ( )n OMe S NHNH2 ii R O O O S ( )n - NHNHCS K + S R O N O ( )n v iv iii R N S R O SH O N O ( )n N O S ( )n SH S O N N S N SH NH2 (i) N2H4. 57 (iv) AcOH (v) N2H4. The multipurpose synthetic applicability and biological activity of these heterocycles will facilitate the medicinal chemists to plan. Furthermore. On the other hand. The deprotection was effected with -cyclodextrin in the presence of iodoxybenzoic acid [224] (Eqn. the desired heterocycles were prepared by protecting the carbonyl group as oxime derivative followed by treatment of potassium dithiocarbazate with respective reagents.3-dipolar cycloaddition of diazomethane to the latter compounds resulted in (4phenyl-4.5-dihydro-1H-pyrazole-4sulfonyl)acetic acid methyl ester. No. 10. novel sulfone linked bis heterocycles pyrazolines in combination with thiadiazoles. phenacylsulfonylacetic acid methyl ester was also used to develop bis-heterocycles. oxadiazoles and triazoles were prepared by appropriate functionalization of olefin and ester moieties in Estyrylsulfonylacetic acid methyl ester and aroylethenesulfonylacetic acid methyl ester. azepinone was obtained instead of the expected acid hydrazide. 227] (Eqn.2. The -ketomethylene group in the former compound was exploited for the construction of selenadiazole. and occupy unique place in the organic chemistry and our lives. design and implement new approaches towards the discovery of novel drugs. 10 Maddila et al. 60). oxadiazole and triazole moieties [225] (Eqn. thiadiazole and diazaphosphole rings and ester functionality for thiadiazole. In addition to these. arylsulfonylethenesulfonyl acetic acid methyl ester was also utilized for the synthesis of pyrrolyloxadiazoles. H2NOCHN N O O OMe O i R O S O OMe ii R R O N S R O O O OMe N Se N R O iv O O S . Apart from these. oxadiazoles and triazoles [226.3selenadiazolyl/thiadiazolyl/diazaphosphonyl oxadiazoles.5-dihydro-1H-pyrazole-3-sulfonyl)acetic acid methyl ester and (3-aroyl-4. With the enormous literature continuously accumulating over the years. but under strong acidic conditions pyrrolyloxadiazole was produced. 59 . 2013. 61). thiadiazoles and triazoles.H2O / Pyridine / EtOH (iv) CS2 / KOH / EtOH / US (v) HCl / H2O (vi) AcOH (vii) N2H4. However. 229] (Eqn. Vol. The potassium dithiocarbazate of the latter compound in the presence of acetic acid get cyclized to pyrrolylthiadiazole. The ester group in these compounds through potassium salt of acid hydrazides was O O S CONCLUSION Triazoles have pronounced biological and medicinal significance. 1. the potassium dithiocarbazate in the presence of hydrazine hydrate afforded pyrrolyltriazole [228. 58). The treatment of former compound with tosylmethylisocyanide resulted in (3arylsulfonyl-1H-pyrrole-4-sulfonyl)acetic acid methyl ester.H2O / H2O R O SH O N N S N N Se N SH NH2 Eqn. Thus. 1.HCl / NaOAc / MeOH (ii) SeO2 / AcOH (iii) N2H4. cyclized to thiadiazoles. the chemistry of triazoles sustains to be a promising field in the years to come.+ NHNHCS K S vi vii R R O N N S O Se N NHNH2 N N v N O Se Se N O S iii O O O N N S S SH N Se N (i) NH2NHCONH2. thiadiazoles and triazoles. 59).708 Letters in Organic Chemistry. Comprehensive heterocyclic chemistry III.V. C.F. Ramsden. pp1-13. 60 N H N H O S SH NH2 N H N H (i) CH2N2 / Et2O / Et3N (ii) N2H4.R. Scriven. 1996... 2008. U. Pergamon: Oxford. Eds.R. R. REFERENCES ACKNOWLEDGEMENTS [1] Authors acknowledge the amenities received from the School of Chemistry and Physics and the financial support [2] Katritzky.H2O / H2O CONFLICT OF INTEREST S O O SH NH2 Eqn..K. Ress. No.H2O / MeOH (iii) CS2 / KOH / EtOH (iv) HCl (v) AcOH (vi) N2H4.F.Triazole Derivatives Letters in Organic Chemistry. 2013. U.H2O H N N SH S N H N S S SH O O O SH Ar S O O S O vi N N O S SH Ar N H The authors confirm that this article content has no conflict of interest. Taylor. A.. E.K. C... Katritzky. Pergamon: Oxford. A. 61 from the University of KwaZulu-Natal in the form of postdoctoral bursaries to SM and RP. Eds. 10.V.H2O / Pyridine / EtOH (iii) CS2 / KOH / EtOH / US (iv) HCl / H2O (v) AcOH (vi) N2H4. S O N N N N H (i) TosMIC / NaH /Et2O / DMSO (ii) N2H4. 1-9.J. Comprehensive heterocyclic chemistry II. 10 R O H O ii S i OMe O O O O S OMe N H R 709 N H R R O O O NHNH2 O O O S S iii - + NHNHCS K N N S N H N H v iv R N O O R R N O N O O S vi N N N N Ar S O O O Ar S O S O O O i Ar OMe O O S H O O S O O O NHNH2 iii Ar Ar S O O S S O O S O O NHNHCS K+ S v O N N O N H ii OMe N H iv O O Eqn...A. .W. Scriven. E. Vol.K.. Arzneimittelforschung.. Bull. Suga. 542-548. V... J.. Hattori. 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