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1.
LU Rong-Jian QIAN Bao-Ying DENG Hai-Yan YANG Hua-ZhengNational Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry Nankai University Tianjin China 《中国化学》1997,(6)
The orientation of the addition of 5-amino-3-benzylthio-1,2,4-triazole and its analogues (pyrazole) (1) with the aryl isocyanate can be directed by controlling the reaction temperature and one of the product, 5-amino-1-arylaminocarbonyl-3-benzylthio-1,2,4-triazole (pyrazole) (2), can rearrange at 170C to another product, 5-arylureylene-3-benzylthio-1,2,4-triazole (pyrazole) (3). A plausible mechanism explanation for this rearrangement reaction was presented. It was suggested that the rearrangement reaction could be referred to the thermodynamics transposition leading to the predominant 5-arylureylene-3-benzylthio-1,2,4-triazole energy preferentially. 相似文献
2.
William T. Monte William A. Kleschick Richard W. Meikle Sigrid W. Snider Jon Bordner 《Journal of heterocyclic chemistry》1989,26(5):1393-1396
The reaction of 3-amino-5-benzylthio-1,2,4-triazole with acetylacetaldehyde dimethyl acetal affords 2-benzylthio-5-methyl-1,2,4-triazolo[1,5a]pyrimidine or 2-benzylthio-7-methyl-1,2,4-triazolo[1,5a]pyrimidine regioselectively depending on the reaction conditions. 相似文献
3.
M. S. Pevzner T. P. Kofman E. N. Kibasova L. F. Sushchenko T. L. Uspenskaya 《Chemistry of Heterocyclic Compounds》1980,16(2):194-199
1-Substituted 3-nitro-5-(N-azolyl)-1,2,4-triazoles mixed with 1-substituted 3-nitro-1,2,4-triazol-5-ones are obtained in the
reaction of 1-substituted 3,5-dinitro-1,2,4-triazoles with anions of heterocyclic NH acids (1,2,4-triazole, 1,2,3-triazole,
pyrazole, benzotriazole, benzimidazole, and indazole derivatives). 1-Methyl-3-nitro-5-amino-1,2,4-triazole is formed instead
of the expected 5-tetrazolyl derivative in the reaction of 1-methyl-3,5-dinitro-1,2,4-triazole with tetrazole in alkaline
media.
See [1] for communication 25.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 257–261, February, 1980. 相似文献
4.
研究了氯代膦酰基异氰酸酯与5-氨基-3-苄硫基-1,2,4-三唑及其类似物的成环反应,合成了12个7-芳基(烷氧基)-2苄硫基-5,7-二氧代-4,5,6,7-四氢-7-磷杂-1,2,4-三唑[1,5a]三嗪,利用1HNMR、31PNMR确定其Z型,生物活性测定结果表明,部分化合物具有一定的除草活性。 相似文献
5.
The results of a study of the regioselection in the reaction of 3-amino-5-benzylthio-1,2,4-triazole with several unsymmetrical 1,3-diketones are reported. The 1,3-diketones studied are 1,1,1-trifluoro-2,4-pentanedione, benzoylacetone and 2-acetylcyclopentanone. Chemical, spectroscopic and X-ray crystallographic data are presented to support structural assignments of the major reaction products. 相似文献
6.
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. 相似文献
7.
The Acylation of 5-Amino-1 H-1,2,4-triazoles. A 13C-NMR. Study The acylation of 3-substituted-5-amino-1 H-1,2,4-triazoles (1) with methyl chloroformate or dimethylcarbamoyl chloride yielded mainly 1-acyl-5-amino-1,2,4-triazoles ( 2 and 3 ). Acylation of 3-methyl-, 3-methoxy- and 3-methylthio-5-amino-1 H-1,2,4-triazole ( 1b , 1c and 1d ) with methyl chloroformate gave up to 10% of the 1-acyl-3-amino-1,2,4-triazoles. For the unsubstituted 5-amino-1,2,4-triazole (1a) , a (1:1)-mixture of the 3- and 5-isomers 2a and 4 was obtained in dioxane in the presence of triethylamine. No 4-acylated product was detected in contrast to earlier reports. The structures of the reaction products were determined with the aid of proton coupled 13C-NMR. spectra using the corresponding N-methyl-1,2,4-triazoles as reference compounds. 相似文献
8.
A general method is reported for the parallel solid-phase synthesis of 5-amino-1-(substituted thiocarbamoyl)pyrazole and 1,2,4-triazole derivatives based on the cyclization of polymer-bound dithiocarbazate 3 with various electrophiles, such as 3-ethoxyacrylonitriles 8 and cyanocarboimidates 9. The polymer-bound dithiocarbazate 3, produced by nucleophilic reaction with carbon disulfide and Fmoc-hydrazine on the Merrifield resin, served as the key intermediate for subsequent heterocycle diversification. Further nucleophilic substitution on these polymer-bound 5-amino-1-dithiocarboxypyrazoles 4 and 1,2,4-triazoles 6 with various amines under thermal cleavage condition produced the desired 5-amino-1-(substituted thiocarbamoyl)pyrazoles 5 and 1,2,4-triazoles 7. The progress of reactions could be monitored as polymer-bound intermediates by ATR-FTIR spectroscopy on single bead. The final compounds, obtained in good four-step overall yields and high purities upon cleavage from the resins, were characterized by LC/MS, 1H NMR, and 13C NMR spectroscopy. 相似文献
9.
Synthesis of new tetrazene(N-N=N-N)-linked bi(1,2,4-triazole) 总被引:2,自引:0,他引:2
Sheng Hua Li Si Ping Pang Xiao Tong Li Yong Zhong Yu Xin Qi Zhao 《中国化学快报》2007,18(10):1176-1178
The reaction of 4-amino-1,2,4-triazole with sodium dichloroisocyanurate (SDCI) afforded new tetrazene(N-N=N-N)-linked bi(1.2,4-triazole) 2a in excellent yield.Increasing the molar ratio of SDCI to 4-amino-1,2,4-triazole,the chlorinated product 1,5,5′- trichloro-4,4′-azo-1,2,4-triazole (2b) was formed.These new compounds have been characterized by MS,~1H NMR,~(13)C NMR,and elemental analysis. 相似文献
10.
在阳离子交换树脂D72存在下5-氨基-3-苄硫基-4-氰基(乙氧羰基)吡唑与苯基二氯化膦和芳醛的类Mannich反应,合成了9个2-苄硫基-3-氰基(乙氧羰基)-5-芳基-6-苯基-6-氧-6-磷杂-4,5,6-三氢咪唑[2,3e]吡唑,利用NMR方法确定其为反式构型,初步研究了反应机制。生物活性测试结果表明,部分化合物具有一定的除草活性。 相似文献
11.
Cyril PÁrkÁnyi Abdou O. Abdelhamid John C. S. Cheng Ahmad S. Shawali 《Journal of heterocyclic chemistry》1984,21(4):1029-1032
Nitroso derivatives of imidazo[1,2-a]pyridine ( 11, 13, 14 ), imidazo[1,2-a]pyrimidine ( 15 ), imidazo[1,2-a]pyrazine ( 16 ), imidazo[1,2-b]pyrazole ( 17 ), and imidazo[1,2-b]-1,2,4-triazole ( 19 ) were obtained in good yields from α-ketohydroximoyl chlorides 3 and 2-aminopyridines ( 4–6 ), 2-aminopyrimidine ( 7 ), 2-aminopyrazine ( 8 ), 5-amino-3-phenylpyrazole ( 9 ), and 3-amino-2H-1,2,4-triazole ( 10 ), respectively. Under different conditions, the reaction of 3 with 3-amino-2H-1,2,4-triazole ( 10 ) and 2-aminopyrazine ( 8 ) afforded the noncyclized substitution products 18 and 22 , respectively. The structures of the products were assigned and confirmed on the basis of their elemental analyses, spectral data, and alternate synthesis wherever possible. 相似文献
12.
利用5-氨基-4-乙氧羰基(或氰基)-3-苄硫基吡唑与异氰酸酯的加成反应合成了一系列1-芳胺羰基-3-苄硫基-4-乙氧羰基(或氰基)-5-氨基吡唑。利用分子力学计算,解释了1HNMR谱中的取代基效应。生物活性测定结果表明部分化合物具有良好的除草活性。 相似文献
13.
V. M. Chernyshev V. A. Rakitov V. A. Taranushich Z. A. Starikova 《Chemistry of Heterocyclic Compounds》2007,43(6):776-780
It has been established by X-ray structural analysis that the initial product of the interaction of 5-amino-1-phenyl-3-p-toluenesulfonylamino-1,2,4-triazole
with p-methylbenzoyl chloride is 5-amino-3-(N-pmethylbenzoyl-N-p-toluenesulfonyl)amino-1-phenyl-1,2,4-triazole.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 917–921, June, 2007. 相似文献
14.
Naeem B. Hanna Slobodan D. Dimitrijevich Steven B. Larson Roland K. Robins Ganapathi R. Revankar 《Journal of heterocyclic chemistry》1988,25(6):1857-1868
1-β-D-Ribofuranosyl- 21 , 1-(2-deoxy-β-D-erytftro-pento fur anosyl)- 27 and 1-β-D-arabinofuranosyl- 29 derivatives of 1,2,4-triazole-3-sulfonamide ( 19 ) have been prepared. Glycosylation of the silylated 19 with 1,2,3,5-tetra-0-acetyl-β-D-ribofuranose ( 5 ) in the presence of trimethylsilyl triflate gave the corresponding blocked nucleoside ( 20 ), which on ammonolysis afforded 1-β-D-ribofuranosyl-1,2,4-triazole-3-sulfonamide ( 21 ). Stereospecific glycosylation of the sodium salt of 19 with either 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose ( 22 ) or 1-chloro-2,3,5-tri-0-benzyl-α-D-arabinofuranose ( 23 ) provided the corresponding protected nucleosides 26 and 28. Deprotection of 26 and 28 furnished 1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,2,4-triazole-3-sulfonamide ( 27 ) and 1-β-D-arabinofuranosyl-1,2,4-triazole-3-sulfonamide ( 29 ), respectively. 2-0-D-Ribofuranosyl-1,2,4-triazole-3(4H)-thione ( 7 ) and 4-β-D-ribofuranosyl-1,2,4-triazole-3(2H)-thione ( 9 ) were also prepared utilizing either an acid catalyzed fusion of 1,2,4-triazole-3(1H,2H)-thione ( 4 ) with 5 , the reaction of 5 with silylated 4 in the presence of trimethylsilyl triflate, or by ring closure of 4-(2,3,5-tri-0-benzoyl-β-D-ribofuranosyl)thiosemicarbazide ( 10 ) with mixed anhydride and subsequent deacylation. The synthesis of 1-β-D-ribofuranosyl-3-benzylthio-1,2,4-triazole ( 15 ) has also been accomplished by the silylation procedure employing 3-benzylthio-1,2,4-triazole ( 13 ) and 5 to give 1-(2,3,5-tri-0-acetyl-β-D-ribofuranosyl)-3-benzylthio-1,2,4-triazole ( 14 ). Deacetylation of 14 furnished 15 . The structural assignments of 7, 14 and 21 were made by single-crystal X-ray diffraction analysis and their hydrogen bonding characteristics have been studied. The sulfonamido-1,2,4-triazole nucleosides are devoid of any significant antiviral or antitumor activity in cell culture. 相似文献
15.
N-Nitroimines: I. Synthesis,Structure, and Properties of 3,5-Diamino-1-nitroamidino-1,2,4-triazole 总被引:1,自引:0,他引:1
Astakhov A. M. Vasil'ev A. D. Gelemurzina I. V. Sokolenko V. A. Kruglyakova L. A. Stepanov R. S. 《Russian Journal of Organic Chemistry》2003,39(1):120-124
The reaction of 3,5-diamino-1,2,4-triazole with 2-methyl-1-nitroisothiourea gives 3,5-diamino-1-nitroamidino-1,2,4-triazole instead of the expected 1-[5(3)-amino-1,2,4-triazol-3(5)-yl]-2-nitroguanidine. Almost planar structure of the molecule of 3,5-diamino-1-nitroamidino-1,2,4-triazole gives rise for direct polar conjugation which is responsible for the low basicity of the amino groups. 相似文献
16.
M. G. Voronkov L. G. Shagun I. A. Dorofeev L. V. Zhilitskaya N. O. Yarosh L. I. Larina 《Russian Chemical Bulletin》2013,62(11):2554-2556
3-Amino-1,4-bis(2-oxopropyl)-4H-1,2,4-triazolium triiodide is the product of the reaction of 3-amino-1,2,4-triazole with 1,3-diiodopropan-2-one in acetone in the absence of bases and phase-transfer catalysts. In dimethyl sulfoxide, conversely, a water soluble polyionene consisting of three aminotriazole rings bound by 1,3-dimethylenecarbonyl bridges is formed. The effect of the solvent on the alkylation of 3-amino-1,2,4-triazole with 1,3-diiodopropan-2-one was studied. 相似文献
17.
Reaction of an arylmethyl halide with 3-amino-1,2,4-triazole ( 1 ) allows the preparation of the three N-aryl-methyl derivatives of 1 bearing the substituent on the heterocyclic nitrogen atoms. In basic medium (methoxide anion in DMF or methanol, or in benzene by phase transfer catalysis), the isomers 3 and 5 substituted at N-1 and N-2 respectively are obtained, while the isomer 4 is isolated from neutral medium (DMF). The isomers 3 and 4 may be also prepared by cyclization of appropriate formylguanidinium derivatives. 3-Arylmethylamino-1,2,4-triazoles 2 may be obtained through reaction of 3-chloro-1,2,4-triazole ( 6 ) with arylmethylamines. Photolysis of the N-arylmethyl-3-amino-1,2,4-triazoles 2-5 in methanol or water-methanol mixture, induces homolytic and heterolytic cleavage of the arylmethyl-C-N bond giving rise to 3-amino-1,2,4-triazole ( 1 ). Thus, compounds 2-5 with arylmethyl groups able to absorb solar light may be considered as potential photoactivatable herbicides. 相似文献
18.
V. A. Shagun O. A. Tarasova B. A. Trofimov 《Russian Journal of Organic Chemistry》2006,42(7):1039-1044
Reactions of pyrrole, imidazole, pyrazole, and 1,2,4-triazole with allene and propyne in the gas phase with formation of the corresponding N-isopropenylazoles were simulated at the RHF/6-31G**, B3LYP/6-31G**, and MP2(full)/6-31G** levels. Dissociation of the N-H bond to give azolate ion is the main constituent of the reaction coordinate. All the examined azoles react preferentially with allene rather than with propyne; their reactivity decreases in the series pyrrole > imidazole > pyrazole > 1,2,4-triazole due to participation of the pyridine type nitrogen atoms in the prototropic propyne-allene rearrangement. 相似文献
19.
3,5-Di(hydroxyalkyl) derivatives of 4-amino-1,2,4-triazole and the corresponding derivatives of 1,2,4-triazole obtained by diazotizing them are converted by reaction with SOCl2 into the hydrochlorides of 4-amino-3,5-di(chloroalkyl)-1,2,4-triazoles and 3,5-di(chloroalkyl)-1, 2,4-triazoles. The dinitrate of 3,5-di(hydroxymethyl)-1,2,4-triazole has been prepared. When the cyanohydrazide of glycolic acid is heated with hydrazine hydrate, 4,5-diamino-3-hydroxymethyl-1, 2,4-triazole is formed. 相似文献
20.
V. M. Chernyshev V. A. Rakitov V. V. Blinov V. A. Taranushich Z. A. Starikova 《Chemistry of Heterocyclic Compounds》2009,45(4):436-444
Alkylation of 3-acylamino-, 5-amino-1-phenyl-3-tosylamino-1,2,4-triazoles and 3,5-diacetylamino-1-phenyl-1,2,4-triazole in
the presence of an equimolar amount of sodium methylate in DMSO occurs regioselectively at the amide (sulfamide) group nitrogen
atom. The benzylation of 3-acetylamino-5-amino-1-phenyl-1,2,4-triazole with excess base and benzyl chloride also alkylates
the amino group at position 5. Alkylamino-1-R-1,2,4-triazoles can be conveniently prepared by alkylation of the corresponding
acetylamino-1,2,4-triazoles in the presence of base and subsequent acid hydrolysis of the N-acetyl-N-alkyl derivatives.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 557–567, April, 2009. 相似文献