Tetrahedron

Indole-3-pyruvic acid oxime ethers and thieno analogues by Heck cyclisation. Application to the synthesis of thia-tryptophans

D Wensbo, S Gronowitz

Index: Wensbo, David; Gronowitz, Salo Tetrahedron, 1996 , vol. 52, # 47 p. 14975 - 14988

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Citation Number: 28

Abstract

N-allylation of N-BOC substituted o-iodo anilines (14a-e) and thienoamines (16, 18, 20) employing methyl or benzyl oxime ethers of ethyl (E)-2-oxo-5-bromo-3-pentenoate 2a, followed by palladium-catalysed Heck cyclisation yielded oxime ethers of Bz-substituted ethyl indole-3-pyruvates (15a-f) and thienopyrroles (17, 19, 21–23). Attempted conversion of 2a into the corresponding tosyl hydrazone or oxime resulted in formation of pyridazine (10 ...