Transition-Metal-Free Cascade Synthesis of 4-Quinolones: Umpolung of Michael Acceptors via Ene Reaction with Arynes.
Org Lett
; 18(15): 3818-21, 2016 08 05.
Article
em En
| MEDLINE
| ID: mdl-27434217
ABSTRACT
A novel "one-pot" aryne transformation is described that affords various 4-quinolone derivatives without recourse to transition-metal catalysis. Arynes react with aza-Morita-Baylis-Hillman (AMBH) adducts through a cascade sequence involving an insertion/cyclization/ene reaction process to afford 4-quinolones in high yields with a broad substrate scope under mild reaction conditions. Essentially, an umpolung of reactivity at the ß carbon of α,ß-unsaturated ketone has been achieved by an inverse electron demand aryne-ene reaction to provide a C-arylated product.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2016
Tipo de documento:
Article