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Type: Artigo de periódico
Title: Heck arylations of N-acyl-3-pyrroline and N-acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts. Short syntheses of aryl gamma- and delta-lactams, baclofen, homobaclofen and analogues
Author: Carpes, MJS
Correia, CRD
Abstract: Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give alpha-hydroxycarbamates (hemiaminals) or alpha-alkoxycarbamates which were oxidized to the desired gamma- and delta-lactams. Acidic hydrolysis of the gamma-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug. in only three steps with ail overall yield of 63 76%, Starting from N-acyl-tetrahydropyridine, aryl-delta-lactams and higher homologues of baclofen can be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron Letters. Pergamon-elsevier Science Ltd, v. 43, n. 5, n. 741, n. 744, 2002.
Rights: fechado
Identifier DOI: 10.1016/S0040-4039(01)02267-5
Date Issue: 2002
Appears in Collections:Unicamp - Artigos e Outros Documentos

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