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

A Takahashi, S Kawai, I Hachiya…

Index: Takahashi, Atsushi; Kawai, Shiho; Hachiya, Iwao; Shimizu, Makoto European Journal of Organic Chemistry, 2010 , # 1 p. 191 - 200

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Citation Number: 12

Abstract

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.