Novel Synthesis of 5-Substituted-3-phenylindole-2-(1,2,4-triazole) Derivatives

Various substituted 3-phenylindole 2-carboxylates (1a-c) were prepared according to the literature methods. These carboxylates (1a-c) on reaction with thiosemicarbazide yielded 5-substituted-3-phenylindol-2-(1,2,4-triazole-3-thione) (2a-c) on refluxing in pyridine for 8 h. The 5-substituted-3-phenyl...

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Bibliographic Details
Published inSynthetic communications Vol. 38; no. 9; pp. 1381 - 1388
Main Authors Veeresha Sharma, P. M., Purohit, M. G.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 01.01.2008
Subjects
3-Phenylindole-2-carboxylates
alkylating agents
Chemistry
Chemistry, Organic
cyclocondensation
Physical Sciences
Science & Technology
thiosemicarbazides
alkylating agents
thiosemicarbazides
3-phenylindole-2-carboxylates
cyclocondensation
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Summary:Various substituted 3-phenylindole 2-carboxylates (1a-c) were prepared according to the literature methods. These carboxylates (1a-c) on reaction with thiosemicarbazide yielded 5-substituted-3-phenylindol-2-(1,2,4-triazole-3-thione) (2a-c) on refluxing in pyridine for 8 h. The 5-substituted-3-phenylindole-2-[1,2,4-triazolo-3-thioacetic acid] (3a-c) were prepared from 5-substituted-3-phenyl indole-2-[1,2,4-triazole-3-thione] (2a-c) on reaction with an appropriate alkylating agent and sodium acetate in acetic acid. Further, (3a-c) were reacted with acetic anhydride to bring about a cyclocondensation reaction to yield 5-substituted-3-phenylindol-2-thiazolo(2,3-b)-triazole (4a-c). The 5-substituted-3-phenylindole-2-[1,2,4-triazolo-3-acetic acid] (3a-c) were reacted with o-phenylenediamino dihydrochloride in ethylene glycol to yield 5-substituted-3-phenylindole-1,2,4-triazolo-3′-yl-thiomethyl)benzimidazoles (5a-c).
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910801914160