Syntheses of some new 4-amino-5-(N-methyl-arylsulfonamido)methyl-1,2,4-triazole-3-thiones and their derivatives

The cyclization of 4-amino-5-(N-methyl-arylsulfonamido)methyl-1,2,4-triazole-3-thiones II , synthesized by the Reid and Heindel approach, with α-chloroacetophenone yields 7II-6-aryl-3-(N-methyl-arylsulfon-amido)methyl-s-triazolo[3,4-b][1,3,4]-thiazines III . Novel compounds II also react with benzyl chloride to afford 4-amino-3-benzylthio-5-(N-methyl-arylsulfonamido)methyl-1,2,4-triazole IV . © 1996 John Wiley & Sons, Inc.     

Synthesis of 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their isatin-3-imine derivatives

Iminoester hydrochlorides 1 have been synthesized. These compounds were then converted into ester ethoxycarbonyl hydrazones 2, from which in turn a new series of substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones, 3, was then prepared.Finally a set of isatin imine derivatives 4 was obtained from the reaction of compounds 3 with isatin. The structures of all the new synthesized compounds were confirmed by elemental analyses, IR, (1)H-NMR and (13)C-NMR spectra.     

Conversion of some substituted 1,2,4-triazole-3-thiones

An N-phenyl substituent and an N-allyl substituent in the 4 position of some substituted 1,2,4-triazole-3-thiones do not affect the course of cyanoethylation and alkylation reactions. Cyanoethylation leads to N-substituted derivatives, whereas alkylation gives S-substituted derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1425–1427, October, 1974.     

Acylation of some substituted 1,2,4-triazole-3-thiones

Acylation of some substituted 1,2,4-triazole-3-thiones in the presence of triethylamine gives N-substituted derivatives. S-Substituted derivatives, which are readily transacylated to the N-substituted derivatives on heating, are formed in the case of 4-phenyltriazolethiones in alkaline media. In the case of 4-allyltriazolethiones acylation in alkaline media gives only the N-substituted derivatives. Bromination of the acyl derivatives gives the disulfides.     

N-芳基-5-氨基-1,2,4-三唑-3-磺酰胺的合成

以5－氨基－3－巯基－1，2，4－三唑为原料，经氯气氧氯化后分别用邻氯苯胺和2，6－二氯苯胺胺解，合成了两个N－芳基－5－氨基－1，2，4－三唑－3－磺酰胺，产品结构经IR和1H NMR确认。     

5-amino-3,4-dihydro-2h-1,2,4-triazole-3-thiones. synthesis and chemosensor properties

The reaction of 4-arylalkyl- and 4-arylthiosemicarbazides with aroyl isothiocyanates gave substituted 1,2-bis(thiocarbamoyl)hydrazines, which readily cyclize to give previously unreported 4-aroyl 5-arylalkyl- and 4-aroyl-5-arylamino-2H-1,2,4-triazole-3-thiones, respectively. A spectral study of 9-anthrylmethylthiosemicarbazides and derived dihydrotriazolethione indicated the chemosensor activity of these compounds relative to a cation series.     

Synthesis of 4-(pyrazol-5-yl)-1,2,4-triazole-3-thiones

Condensation of pyrazolyl isothiocyanates 2 with N-substituted hydrazines provided the 2-methyl/phenyl-4-(pyrazol-5-yl)thiosemicarbazides 3 . Cyclization of 3 with formic acid-acetic anhydride or with triethyl orthoacetate-acetic anhydride provided 4-(pyrazol-5-yl)-l,2,4-triazole-3-thiones 4a-f and 5-methyl-4-(pyrazol-5-yl)-1,2,4-triazole-3-thiones 4g-I respectively.     

Mesoionic 1-amino-1,3,4-triazole-2-thiones and their azomethine derivatives

The reaction of triethylammonium salts of -acyldithiocarbazic acids with sodium chloroacetate and hydrazine leads to the formation of mesoionic 1-amino-1,3,4-triazole-2-thiones, which react with aldehydes to give the corresponding azomethine derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 424–428, March, 1976.     

Synthesis and spectral studies of organotin(IV) 4-amino-3-alkyl-1,2,4-triazole-5-thionates: in vitro antimicrobial activity

Some di- and triorganotin(IV) triazolates of general formula, R(4-n)SnLn (where n=2; R=Me, n-Bu and Ph; n=1; R=Me, n-Pr, n-Bu and Ph and HL=4-amino-3-methyl-1,2,4-triazole-5-thiol (HL-1); and 4-amino-3-ethyl-1,2,4-triazole-5-thiol (HL-2)) were synthesized by the reaction of R(4-n)SnCln with sodium salt of HL-1 and HL-2. The bonding and coordination behavior in these derivatives have been discussed on the basis of IR and 119Sn M?ssbauer spectroscopic studies in the solid state. Their coordination behavior in solution is discussed by multinuclear (1H, 13C and 119Sn) NMR spectral studies. The IR and 119Sn M?ssbauer spectroscopic studies indicate that the ligands, HL-1 and HL-2 act as a monoanionic bidentate ligand, coordinating through Sexo- and Nring. The distorted skew trapezoidal-bipyramidal and distorted trigonal bipyramidal geometries have been proposed for R2SnL2 and R3SnL, respectively, in the solid state. In vitro antimicrobial screening of some of the newly synthesized derivatives and of some di- and triorganotin(IV) derivatives of 3-amino-1,2,4-triazole-5-thiol (HL-3) and 5-amino-3H-1,3,4-thiadiazole-2-thiol (HL-4) along with two standard drugs such as fluconazole and ciprofloxacin have been carried out against the bacteria, viz. Staphylococcus aureus and Escherichia coli, and against some fungi, viz. Aspergillus fumigatus, Candida albicans, Candida albicans (ATCC 10231), Candida krusei (GO3) and Candida glabrata (HO5) by the filter paper disc method. The studied organotin(IV) compounds show mild antifungal activity as compared to that of fluconazole, however, they show almost insignificant activity against the studied Gram-positive (Staphylococcus aureas) and Gram-negative (Escherichia coli) bacteria as compared to that of standard drug, ciprofloxacin.     

Synthesis of esters and amides of 5-amino-1,2,4-triazole-3-carboxylic and 5-amino-1,2,4-triazol-3-ylacetic acids

Various synthetic routes to esters and amides of 5-amino-1,2,4-triazole-3-carboxylic and 5-amino-1,2,4-triazol-3-ylacetic acids were examined.     

Synthesis of 1,2,4-triazole-3-thiols and their S-substituted derivatives

New 1,2,4-triazole-3-thiols were synthesized by reactions of the corresponding carboxylic acid hydrazides with isothiocyanates and subsequent cyclization of intermediate 1,4-substituted thiosemicarbazides. Alkylation of 1,2,4-triazole-3-thiols with benzyl chlorides and bromacetophenones gave only S-substituted derivatives.     

Synthesis of some new 4,5-substituted-4H-1,2,4-triazole-3-thiol derivatives

In this study appropriate hydrazide compounds, furan-2-carboxylic acid hydrazide (1) and phenylacetic acid hydrazide (2) were converted into 1,4-substituted thiosemicarbazides 4a-e and 5a-e and 4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7 and 10. The 1,4-substituted thiosemicarbazides were then converted into 5-(furan-2-yl or benzyl)-4-(aryl)-4H-1,2,4-triazole-3-thiols 8a-e and 9a-e. In addition, the azomethines 11a-d and 12a-d were prepared from the corresponding arylaldehydes and the 4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7 and 10. The structures of all the synthesized compounds were confirmed by elemental analyses, IR, (1)H-NMR and(13) C-NMR spectra.     

Synthesis, characterization and antifungal evaluation of 5-substituted-4-amino-1,2,4-triazole-3-thioesters

A series of 5-substituted-4-amino-1,2,4-triazole-3-thioesters was synthesized by converting variously substituted organic acids successively into the corresponding esters, hydrazides, 5-substituted-1,3,4-oxadiazole-2-thiols, 5-substituted-1,2,4-triazole-2-thiols and 5-substituted-1,3,4-oxadiazole-2-thioesters. Finally the target compounds were obtained by refluxing 5-substituted-1,3,4-oxadiazole-2-thioesters in the presence of hydrazine hydrate and absolute alcohol. The structures of the synthesized compounds were established by physicochemical and spectroscopic methods. The synthesized compounds were evaluated for their in vitro antifungal activity. Some of the evaluated compounds possessed significant antifungal activity as compared to a terbinafine standard.     

1-苯基-5-芳基-1,2-二氢-1,2,4-三唑-3-硫酮的合成

将取代苯甲酰氯1a～1f与硫氰酸钾反应, 得到的中间体不需纯化直接与苯肼反应, 成功地合成了1-苯基-5-芳 基-1,2-二氢-1,2,4-三唑-3-硫酮(2a～2f). 化合物2的结构通过红外光谱、核磁共振光谱和高分辨质谱进行了表征.     

Synthesis of divinyl derivatives of 5-substituted l,2,4-triazole-3-thiones

Conclusions The reaction of 5-methyl-, 5-phenyl- and 5--furyl-l,2,4-triazole-3-thiones with acetylene gave their N 1, S- and N 2, S-divinyl derivatives.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1674–1676, July, 1986.