Reactions of 3-benzylindole-2-carbohydrazides: Synthesis of new 10-Benzyl-1,2-dihydro-1-oxo-1,2,4-triazino[4,5-a]indoles and 3-Benzyl-2-(1,3,4-oxadiazol-2-yl)indoles

✍ Scribed by Shambabu Joseph Maddirala; Vidya S. Gokak; Linganagouda D. Basanagoudar

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2004
• Tongue: English
• Weight: 144 KB
• Volume: 41
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570410102

✦ Synopsis

Abstract

3‐Benzylindole‐2‐carbohydrazides (4) on reaction with triethylorthoformate in a polar solvent like DMF yielded only 10‐benzyl‐1,2‐dihydro‐1‐oxo‐1,2,4‐triazino[4,5‐a]indoles (5) while (4) on reaction with triethylorthoacetate in DMF yielded both 10‐benzyl‐4‐methyl‐1,2‐dihydro‐1‐oxo‐1,2,4‐triazino[4,5‐a]indoles (5) and 3‐benzyl‐2‐(5‐methyl‐1,3,4‐oxadiazol‐2‐yl)indoles (6) instead of only the triazinoindoles as expected. The oxadiazolylindoles (6) were also synthesized by refluxing (4) with excess of orthoesters. The structures of the compounds formed were characterized by their analytical and spectral data.