Studies on Indole Derivatives. XVII. The Synthesis of Indoxyl Derivatives. (3) The Reactions of 3-Hydroxy-2-(1-methylthiovinyl)-indole Derivatives with Amines

Abstract

Reaction of 1-acetyl-3-hydroxy-2-(2-methoxycarbonyl-1-methylthiovinyl)indole derivatives (Ia-d) and amines afforded the corresponding amino derivatives (V and X) with 4-aminopyrano[3, 2-b]indol-2-one derivatives and 2-amino-3H-pyrrolo[1, 5-a]indol-3-one derivatives. Application of hydrazine hydrate to Id gave a compound (XII) with pyrazolone in α-position of indole. Reaction of Id with diethylamine gave 9-amino-1-methylthio 3H-pyrrolo[1, 5-a]indol-3-ones (XI), while the reaction of Ie with amines gave 1, 9-di-amino-3H-pyrrolo[1, 5-a]indol-3-one derivatives (XIVa, b).