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; Kevin N. Winzenberg

doi:10.1071/CH05188

RESEARCH ARTICLE

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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 and Kevin N. Winzenberg ^A ^B

+ Author Affiliations

- Author Affiliations

^A CSIRO Molecular and Health Technologies, Clayton South VIC 3169, Australia.

^B Corresponding author. Email: kevin.winzenberg@csiro.au

Australian Journal of Chemistry 58(12) 870-876 https://doi.org/10.1071/CH05188
Submitted: 5 August 2005 Accepted: 25 November 2005 Published: 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.

Acknowledgments

We thank E. I. du Pont de Nemours and Co., Agricultural Products Department, for the evaluation of herbicide activity. We thank R. Ian Willing and Peter Pajalic for some NMR experiments and Carl Braybrook for the measurement of mass spectra.

References

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

Abstract

Acknowledgments

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