TY - JOUR
T1 - Regioselective synthesis of 1,2-dihydroquinolines by a solvent-free MgBr2-catalyzed multicomponent reaction
AU - Gutiérrez, Rsuini U.
AU - Correa, Hans C.
AU - Bautista, Rafael
AU - Vargas, José Luis
AU - Jerezano, Alberto V.
AU - Delgado, Francisco
AU - Tamariz, Joaquín
PY - 2013/10/4
Y1 - 2013/10/4
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84885126347&partnerID=8YFLogxK
U2 - 10.1021/jo400973g
DO - 10.1021/jo400973g
M3 - Artículo
C2 - 24044723
SN - 0022-3263
VL - 78
SP - 9614
EP - 9626
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -