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One‐Pot Synthesis of Functionalized Indoles by Cyclization of Lithiated Amides and Nitriles with Oxaldiimidoyl Dichlorides
Author(s) -
Langer Peter,
Anders Joachim T.,
Döring Manfred
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200110)2001:20<3953::aid-ejoc3953>3.0.co;2-h
Subject(s) - chemistry , oxalic acid , acetic acid , medicinal chemistry , organic chemistry
The reaction of the dianion of phenylacetonitrile with substituted oxalic acid bis(imidoyl)chlorides resulted in the formation of 2‐alkylidene‐3‐iminoindoles, containing substituents at different positions of the heterocyclic nucleus. The cyclization of lithiated amides with bis(imidoyl)chlorides afforded (3‐imino‐2,3‐dihydro‐1 H ‐indol‐2‐ylidene)acetic amides. Excellent regio‐ and E ‐diastereoselectivities were observed in all reactions.