SYNTHESIS AND RETRO AZA DIELS-ALDER REACTION OF SOME NEW ISOQUINUCLIDINE DERIVATIVES
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
20/10/2012
20/10/2012
2009
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| Resumo |
N-Benzyl- and N-(alpha-methoxycarbonylethyl)-2,4,6-triphenyl-1,2-dihydropyridines were submitted to Diels-Alder reactions with maleic anhydride or N-phenylmaleimide yielding, diastereoselectively, the corresponding endo-anti adducts. These novel isoquinuclidines showed to be resistant to N-alkylation or N-protonation, undergoing an unexpected fragmentation via a retro aza Diels-Alder process. Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) FAPESP CAPES Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) CNPq Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) |
| Identificador |
HETEROCYCLES, v.78, n.5, p.1223-1233, 2009 0385-5414 http://producao.usp.br/handle/BDPI/31197 10.3987/COM-08-11610 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
| Relação |
Heterocycles |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #Retro-Aza Diels-Alder Reaction #Isoquinuclidine #endo-Anti Adduct #1,2-Dihydropyridine #Phenyl Substituted Diene #PRIMARY AMINES #2-AZANORBORNENES #DEAMINATION #Chemistry, Organic |
| Tipo |
article original article publishedVersion |
