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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 restrictedα-acyl-β-aminovinyl ketones

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors
  1. O. V. Gulyakevich
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  2. A. S. Lyakhov
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  3. A. L. Mikhal'chuk
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Institute of Bioorganic Chemistry, Belarus Academy of Sciences, Minsk 22014. Scientific-Research Institute of Physicochemical Problems, Belorussian State University, Minsk 220080. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 965–974, July, 1996. Original article submitted September 27, 1995.

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Gulyakevich, O.V., Lyakhov, A.S. & Mikhal'chuk, A.L. 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 restrictedα-acyl-β-aminovinyl ketones. Chem Heterocycl Compd 32, 826–834 (1996). https://doi.org/10.1007/BF01165729

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