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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
Author(s) -
Ahmed Quazi,
WagnerJauregg Theodor,
Pretsch Ernst,
Seibl Josef
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560521
Subject(s) - succinimides , chemistry , lithium aluminium hydride , lithium (medication) , benzimidazole , alkyl , medicinal chemistry , aryl , aluminum hydride , organic chemistry , catalysis , medicine , endocrinology , methoxide
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.