Exploiting the divergent reactivity of α-isocyanoacetate: multicomponent synthesis of 5-alkoxyoxazoles and related heterocycles.
Chemistry
; 17(3): 880-9, 2011 Jan 17.
Article
en En
| MEDLINE
| ID: mdl-21226103
ABSTRACT
A novel multicomponent synthesis of 5-alkoxyoxazoles, based on a new reactivity profile of α-isocyanoacetates, is described. Thus, simply heating a solution of amine, aldehyde, and α-(EWG-phenyl)-α-isocyanoacetate or α-(4-pyridyl)-α-isocyanoacetate (EWG=electron-withdrawing group) in toluene provided 5-alkoxyoxazoles in good to excellent yields. Reaction of the 5-alkoxyoxazoles with various α,ß-unsaturated acyl chlorides led to the formation of epoxytetrahydropyrrolo[3,4-b]pyridin-5-ones by a domino N-acylation/Diels-Alder cycloaddition sequence. Subsequent fragmentation under basic conditions provided 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. A four-component synthesis of the pyridin-5-one compounds, without isolation of the 5-alkoxyoxazole, was subsequently developed.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Oxazoles
/
Fenilacetatos
/
Isocianatos
/
Alcanos
/
Compuestos Heterocíclicos
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2011
Tipo del documento:
Article
País de afiliación:
Francia