✦ LIBER ✦

A Novel Synthesis of 1-Aryl-9-alkyl-2, 3, 3a, 4, 9, 9a-hexahydro-1H-pyrrolo[2, 3-b] quinoxalines by lithium aluminium hydride reduction of N-phenyl-1-benzimidazolyl-succinimides

✍ Scribed by Quazi Ahmed; Theodor Wagner-Jauregg; Ernst Pretsch; Josef Seibl

Publisher: John Wiley and Sons
Year: 1973
Tongue: German
Weight: 629 KB
Volume: 56
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19730560521

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✦ Synopsis

Abstract

The N‐substituted 1‐benzimidazolyl‐succinimides 6a–v (Scheme 1, Table 1 and 2) have been prepared by the reaction of benzimidazole and its derivatives with maleimides. Reduction of the N‐cyclohexyl and N‐cyclo‐octyl substituted 1‐benzimidazolyl‐succinimides 6i–k with lithium aluminium hydride gives the normally expected substituted (N‐alkyl‐3‐pyrrolidinyl)benzimidazoles 14i–k. However by LiAlH~4~‐reduction of the N‐phenyl substituted 1‐benzimidazolylsuccinimides 6a–h mainly the 1‐aryl‐9‐alkyl‐2, 3, 3a, 4, 9, 9a‐hexahydro‐1__H__‐pyrrolo[2, 3‐b]quinoxalines 7a–h are obtained. The mechanism of this unusual reduction has been elucidated.

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