Studies with 2-arylhydrazononitriles: a new convenient synthesis of 2, 4-disubstituted- 1,2,3-triazole-5-amines

Abstract

A new simple and efficient approach to 2,4-disubstituted 1,2,3-triazoles-5-amines from the reaction of 2-arylhydrazononitriles and hydroxylamine is described. Investigation of behavior of 3-phenyl-3oxo-2-arylhydrazonopropane nitriles has been undertaken. In addition to readily reported formation of aminoisoxazoles, 4-benzoyl-1-aryl-1,2,3-triazole-5-amines 5f,g were prepared via cyclising products of reacting 2f,g with hydroxylamine in basic medium.

Crystal structure and Hirshfeld surface analysis of 4-azido-2-(3,5-dimethylphenyl)-5-(4-nitrophenyl)-2H-1,2,3-triazole

“…In general, the development of new synthesis methods for 2H-1,2,3-triazole derivatives has been a constant in the field of organic synthesis. Since the 1,2,3-triazole ring is an integral part of many medicinal preparations, research on their synthesis (Kamijo et al, 2002;Liu et al, 2008;Ghozlan et al, 2006;Kalisiak et al, 2008;Koszytkowska-Stawin ´ska et al, 2012) and biological activities is constantly increasing (Ferreira et al, 2013;Tan et al, 2002;Prusiner & Sundaralingam, 1973;Toniolo et al, 2017;Caliendo et al, 1999;Blass et al, 2006;von Mutius et al, 2012;Ferreira et al, 2013). In particular, we can mention the synthesis of new 1,2,3-triazole-based drugs against tuberculosis (Sanna et al, 2000).…”

1,2,3-Triazoles

“…Treatment of hydrazones 1153 with hydroxylamine affords amidoximes 1154 in high yield. Upon heating with anhydrous sodium acetate in refluxing DMF, compounds 1154 undergo intramolecular cyclocondensation to provide 5-substituted 4-amino-2-aryl-2 H -1,2,3-triazoles 1155 in 75–85% yield ( Scheme 190 ) <2006ARK(xv)53> .

Scheme 190

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Novel hybrid thiazoles, bis-thiazoles linked to azo-sulfamethoxazole: Synthesis, docking, and antimicrobial activity

“…The resulting scaffolds may be capable of overcoming drug resistance while also increasing activity and binding affinity [ [38] , [39] , [40] , [41] ]. Based on the aforementioned hypotheses and our continued endeavor towards the synthesis of heterocycles [ [42] , [43] , [44] , [45] , [46] , [47] , [48] , [49] , [50] , [51] , [52] , [53] , [54] , [55] , [56] , [57] , [58] , [59] , [60] , [61] , [62] , [63] , [64] , [65] , [66] , [67] , [68] , [69] , [70] , [71] , [72] ] we report herein the synthesis of some thiazoles, bis(thiazoles), and [ 1 , 2 , 4 ]triazolo[3,4- b ] [ 1 , 3 , 4 ]thiadiazines linked to hydrazinyl- N -(5-methylisoxazol-3-yl)benzenesulfonamide moiety as novel hybrid molecules and evaluation their bioactivities against different bacterial strains and fungal strains; in an attempt to conquer sulfonamide resistance and find novel therapeutic options. Furthermore, the potential binding interactions of the novel compounds with the active sites of different target enzymes were investigated using molecular docking simulations.…”