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A New Method for the Synthesis of Multisubstituted Pyrroles of Biological Interest by Double Nucleophilic Addition to α,β-Unsaturated Imines

✍ Scribed by Atsushi Takahashi; Shiho Kawai; Iwao Hachiya; Makoto Shimizu

Publisher: John Wiley and Sons
Year: 2009
Tongue: English
Weight: 270 KB
Volume: 2010
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200901055

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✦ Synopsis

Abstract

Double nucleophilic addition reactions of dialkoxy ketenesilyl acetals proceeded with α,β‐unsaturated imines to give 1,4‐ and 1,2‐double addition products, and their subsequent transformations afforded multisubstituted pyrroles in good yields. Application of this procedure to the synthesis of an imidazole glycerol phosphate dehydratase inhibitor (IGPDI), a physiologically active 2,3,5‐trisubstituted pyrrole, is also described.

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