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Synthesis of 1,3,4-oxa(or thia)diazaheterocycles starting from 2-(pyrrol-1'-y1)phthalimide

✍ Scribed by Anita Guesdon; Alain Fogain-Ninkam; Bernard Decroix; Pierre Netchitaïlo

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
52 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

1‐(1,3‐Dioxo‐1,3‐dihydro‐2__H__‐isoindol‐2‐yl)‐1__H__‐pyrrol‐2 carbaldehyde 4 was synthesized by Vilsmeier‐Haack reaction from 2‐(pyrrol‐1‐yl) phthalimide. Reduction of 4 by sodium borohydride, or action of Grignard reagents on 4 led to the corresponding alcohols 5 which were cyclized to pyrroloxadiazino isoin‐doles 1 by heating in the presence of silica gel. Transformation of the hydroxylactam 6 with acetic acid derivatives led to the esters 7 which gave, after saponification, pyrroloxa(or thia)diazepinoisoindolones 2 by intramolecular cyclization.

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