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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 γ- And δ-lactams, Baclofen, Homobaclofen And Analogues
Author: Carpes M.J.S.
Correia C.R.D.
Abstract: Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give α-hydroxycarbamates (hemiaminals) or α-alkoxycarbamates which were oxidized to the desired γ- and δ-lactams. Acidic hydrolysis of the γ-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug, in only three steps with an overall yield of 63-76%. Starting from N-acyl-tetrahydropyridine, aryl-δ-lactams and higher homologues of baclofen can be obtained. © 2002 Elsevier Science Ltd. All rights reserved.
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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