Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/73561
Type: Artigo de periódico
Title: The intramolecular Heck reaction and the synthesis of indolizidinone, quinolizidinone and benzoazepinone derivatives
Author: Santos, LS
Pilli, RA
Abstract: The intramolecular Heck cyclization of N-allyl, -aryl- or -benzyl-5-allyl-2-pyrrolidinones and N-allyl- -aryl- or -benzyl-6-allyl-2-piperidinones (1a-f), prepared through allyltrimethylsilane addition to the corresponding cyclic N-acyliminium ions, afforded indolizidinones (3a, 5a, 5b), quinolizidinones (3b, 4b) and benzoazepinones (7a, 8a, 7b, 8b) in moderate to good yields (56-90%). Exclusive exo-trig over endo-trig mode of cyclization was observed in all examples investigated. and it was accompanied by double bond migration. which precluded our attempts of a one-pot tandem Diels-Alder cycloaddition with dienophiles such as maleic anhydride, methyl vinyl ketone and diethyl azodicarboxy late. Catalytic hydrogenation of a 2:1 mixture of regioisomeric indolizidinones 5a-5b afforded the stereoisomerically enriched cis indolizidinone 6a (20:1 mixture) in quantitative yield. A similar behavior was observed in the catalytic hydrogenation of regioisomeric benzoazepinones 7b-8b.
Subject: Heck reaction
intramolecular cylization
hydrogenation
Country: Alemanha
Editor: Georg Thieme Verlag Kg
Rights: aberto
Date Issue: 2002
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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