Functionalization of 8-aza-D-homogona-1,3,5(10),13-tetraene-12,17a-diones at positions 11 and 17 under the conditions of the Claisen ester condensation. Synthesis and properties of 11- and 17-acylsubstituted 8-aza-D-homogonanes

Abstract

It was shown that 8-aza-D-homogona-1,3,5(10),13-tetraene-12,17a-diones enter into the Claisen ester condensation at the C(₍₁₁₎H₂ and C₁₇H₂ groups, whereas the C₍₁₅₎H₂ group is inert under the investigated conditions. It was established that the direction of the reaction is determined by the structure of the 8-azasteroid substrate. In the presence of a bulky gem-dimethyl group at position 16 the reaction takes place exclusively at the C₁₁H₂ group, while in the absence of this restriction the C₍₁₁₎H₂ and C₍₁₇₎H₂ groups are equivalent. The data from IR, UV, and ¹H and ¹³C NMR spectroscopy of the initial and synthesized derivatives of 3-aza-D-homogonanes are presented and discussed.

How to Cite
Gulyakevich, O. V.; Mikhal'chuk, A. L.; Akhrem, A. A. Chem. Heterocycl. Compd. 1995, 31, 835. [Khim. Geterotsikl. Soedin. 1995, 959.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01170745