Dihydroquinolines, Dihydronaphthyridines and Quinolones by Domino Reactions of Morita-Baylis-Hillman Acetates.

ABSTRACT: An efficient synthetic route to highly substituted dihydroquinolines and dihydronaphthyridines has been developed using a domino reaction of Morita-Baylis-Hillman (MBH) acetates with primary aliphatic and aromatic amines in DMF at 50-90 °C. The MBH substrates incorporate a side chain acetate positioned adjacent to an acrylate or acrylonitrile aza-Michael acceptor as well as an aromatic ring activated toward S_NAr ring closure. A control experiment established that the initial reaction was an S_N2'-type displacement of the side chain acetate by the amine to generate the alkene product with the added nitrogen nucleophile positioned trans to the S_NAr aromatic ring acceptor. Thus, equilibration of the initial alkene geometry is required prior to cyclization. A fu

SUBMITTER: Annor-Gyamfi JK 

PROVIDER: S-EPMC7914960 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature