Tetrahedron

Synthesis of pyrrolo [3, 2-b] benzofurans and pyrrolo [3, 2-b] naphthofurans via addition of a silyloxypyrrole to activated quinones

MA Brimble, C Burgess, R Halim, M Petersson, J Ray

Index: Brimble, Margaret A.; Burgess, Caryn; Halim, Rosliana; Petersson, Maria; Ray, Jayanta Tetrahedron, 2004 , vol. 60, # 27 p. 5751 - 5758

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Citation Number: 28

Abstract

The uncatalyzed reaction of N-(tert-butoxycarbonyl)-2-tert-butyldimethylsilyloxypyrrole with 1, 4-quinones bearing an electron withdrawing group at C-2 has been studied. Use of 1, 4- quinones, bearing an ester group at C-2 provided an efficient synthesis of the respective pyrrolidinobenzofuran adduct or pyrrolidinonaphthofuran adduct whereas use of 1, 4- quinones, and bearing an acetyl group at C-2 afforded silyloxypyrroles, and resulting from ...