Regioselective synthesis of 1,2-dihydroquinolines by a solvent-free MgBr2-catalyzed multicomponent reaction.
J Org Chem
; 78(19): 9614-26, 2013 Oct 04.
Article
em En
| MEDLINE
| ID: mdl-24044723
A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Quinolinas
/
Solventes
/
Brometos
/
Compostos de Magnésio
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2013
Tipo de documento:
Article
País de afiliação:
México
País de publicação:
Estados Unidos