We have recently developed a one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58-90%).1 3-Hexynoic acid was converted to its acyl chloride which upon addition of InCl3 was cyclized to 3-chloro-2-cyclohexenone.  Subsequent addition of alcohol nucleophiles led to a variety of 3-alkoxy-2-cyclohexenones.  We are now applying these conditions toward the preparation of related dihydropyranones and dihydropyridones. Synthesis of a-propargyloxyacetic acids and N-propargyl amino acids will be presented along with cyclization data.  1.     Hylden, A. T.; Uzelac, E. J.; Ostojic, Z.; Wu, T-T; Sacry, K. L.; Sacry, K. L.; Xi, L.; Jones, T. N. �Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones� Beilstein J. Org. Chem. 2011  , 7, 1323-1326.

Application of the alkynoic acid cyclization toward the preparation of heterocyclic compounds

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.