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Synthesis of perimidine and fused perimidine derivatives from reaction of 1,8-naphthalenediamine with an iminoisocoumarin

✍ Scribed by Leslie W. Deady; Thomas Rodemann

Book ID: 102340342
Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 265 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350633

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✦ Synopsis

Abstract

The isocoumarin derivative 1__H__‐1‐acetylimino‐3‐methylbenzo[c]pyran‐4‐carbonitrile reacts with 1,8‐naphthalenediamine under basic conditions to give, primarily, 12‐acetylisoquino[2,1‐a]perimidin‐13‐amine. This undergoes a variety of reactions to give other isoquino[2,1‐a]perimidine derivatives, ring opening to 2‐(1__H__‐perimidin‐2‐yl)phenylacetic acid derivatives and, in polyphosphoric acid, a new hexacyclic system, 6‐methyl‐7,13,13d‐triazadibenzo[def,qr]chrysene.

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