Preparation of 1-[(3-trifluoromethyl)phenyl]-3,4-dihydro-2(1H)-pyridinone derivatives from aza annulation reactions of N-[(3-trifluoromethyl)phenyl]-substituted enaminones

Reaction of 3-trifluoromethylaniline with the 1,3-diketones 1a-1c and 5a-5d affords the N-[(3-trifluoromethyl)phenyl]-substituted enaminones 2a-2c and 6a-6d. Reaction of 2a with the acryloyl chloride derivatives 3a-3c gives the 1-[(3-trifluoromethyl)phenyl]-3,4-dihydro-2(1H)-pyridinones 4a, 4c, 4d; in a similar manner the 2(1H)-pyridinone 4b is obtained from 2b. Reaction of 6c, 6d with acryloyl chloride affords the 2,5(1H,3H)-quinolinedione derivatives 7 and 9 together with the acrylamides 8a, 8b. The 2(1H)-pyridinones 12a, 12b and the 3,4-dihydro-2(1H)-pyridinone 13 are prepared using routes involving the reaction of 2a with ethyl propiolate, dimethyl acetylenedicarboxylate, and maleic anhydride.