Interaction of 8-aza-D-homogona-1,3,5(10),13-tetraene-12,17a-diones with acetic anhydride — New directions in the transformation of conformationally restricted α-acyl-β-aminovinyl ketones

Abstract

The interaction of 16,16-dimethyl-8-aza-D-homogona-1,3,5(10),13-tetraene-12,17a-diones with acetic anhydride has been investigated. In the presence of fused sodium acetate, the major products are 11-vinyl-16,16-dimethyl-8-aza-D-homogona-1,3,5(10),9(11),13-pentaene-12,17a-dione; minor products are 16,16-dimethyl-8-aza-D-homogona-1,3,5(10),9(11),13,17-hexaen-12-ones. In the absence of sodium acetate, the reaction stops at the 11-acetyl-16,16-dimethyl-8-aza-D-homogona-1,3,5(10),13-tetraene-12,17a-dione derivative. In the case of 2,3-demethyoxy-8-aza-D-homogonane, a different principal product is formed, regardless of whether or not sodium acetate is present; this is a compound that results from the formation of a bond between the orignal homogonane and 8-aza-D-homogona-1,3,5(10),9(10),13,17-hexaen-12-one (which is formed during the course of the reaction) at positions 9 and 4, respectively. The structure of the compounds that were obtained has been verified by a set of physicochemical data (IR and UV spectra, PMR, and X-ray diffraction). A probable scheme is proposed for the basic directions of the reaction.

How to Cite
Gulyakevich, O. V.; Lyakhov, A. S.; Mikhal'chuk, A. L. Chem. Heterocycl. Compd. 1996, 32, 826. [Khim. Geterotsikl. Soedin. 1996, 965.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01165729