The intramolecular Heck reaction and the synthesis of indolizidinone, quinolizidinone and benzoazepinone derivatives

dc.creatorSantos, LS
dc.creatorPilli, RA
dc.date2002
dc.dateJAN
dc.date2014-11-14T13:29:38Z
dc.date2015-11-26T16:06:43Z
dc.date2014-11-14T13:29:38Z
dc.date2015-11-26T16:06:43Z
dc.date.accessioned2018-03-28T22:55:32Z
dc.date.available2018-03-28T22:55:32Z
dc.identifierSynthesis-stuttgart. Georg Thieme Verlag Kg, n. 1, n. 87, n. 93, 2002.
dc.identifier0039-7881
dc.identifierWOS:000173162400016
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/73561
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/73561
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/73561
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1265984
dc.descriptionThe 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.
dc.description1
dc.description87
dc.description93
dc.languageen
dc.publisherGeorg Thieme Verlag Kg
dc.publisherStuttgart
dc.publisherAlemanha
dc.relationSynthesis-stuttgart
dc.relationSynthesis
dc.rightsaberto
dc.sourceWeb of Science
dc.subjectHeck reaction
dc.subjectintramolecular cylization
dc.subjecthydrogenation
dc.subjectN-acyliminium Ions
dc.subjectPalladium-catalyzed Cyclizations
dc.subjectPhase-transfer Conditions
dc.subjectAllylic Alcohols
dc.subjectAryl Halides
dc.subjectArylation
dc.subjectSystems
dc.subjectConstruction
dc.subjectVinylation
dc.subjectAmines
dc.titleThe intramolecular Heck reaction and the synthesis of indolizidinone, quinolizidinone and benzoazepinone derivatives
dc.typeArtículos de revistas


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