Preparation of 1-[(3-Trifluoromethyl)phenyl]-3,4-dihydro-2(1H)-pyridinone Derivatives from Aza Annulation Reactions of N-[(3-Trifluoromethyl)phenyl]-Substituted Enaminones

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Contents Vol 58(12)

doi:10.1071/CH05188

Preparation of 1-[(3-Trifluoromethyl)phenyl]-3,4-dihydro-2(1H)-pyridinone Derivatives from Aza Annulation Reactions of N-[(3-Trifluoromethyl)phenyl]-Substituted Enaminones

Abdelselam A. Ali ^A, Kevin N. Winzenberg ^A ^B

^A CSIRO Molecular and Health Technologies, Clayton South VIC 3169, Australia.
^B Corresponding author. Email: kevin.winzenberg@csiro.au





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Australian Journal of Chemistry 58(12) 870–876 http://dx.doi.org/10.1071/CH05188
Submitted: 5 August 2005 Accepted: 25 November 2005 Published online: 20 December 2005

Abstract

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.