SYNTHESIS OF 2-CHLORONICOTINATES, NICOTINATE AND PIRAZINOATE OF 7-SUBSTITUTED 19-NORTESTOSTERONES
https://doi.org/10.29235/1561-8331-2018-54-1-80-86
Abstract
New 7a- and 7b-methyl-19-nortestosterone derivatives bearing nicotinic, 2-chloronicotinic and pyrazinecarboxylic acids fragments at C-17 have been prepared. The key intermediate, 19-nor-6-dehydrotestosterone acetate, was synthesized from solasodine. A copper (II) acetate catalyzed 1,6-conjugate addition of methylmagnesium iodide to 19-nor6-dehydrotestosterone acetate led to a mixture of 17b-acetoxy-7a-methylestr-4-en-3-one as major product and its 7b-isomer. Methanolysis and subsequent acylation of the resulting compounds with 2-chloronicotinoyl chloride, nicotinoyl chloride and pyrazinecarbonyl chloride gave the corresponding target 17b-(2-chloronicotinoyloxy)-7a-methylestr-4-en-3-one, 17b-(2-chloronicotinoyloxy)-7b-methylestr-4-en-3-one, 17b-nicotinoyloxy-7a-methylestr-4-en-3-one, 17b-pyrazinecarbonyloxy-7a-methylestr-4-en-3-one.
About the Authors
M. U. Kauhanka
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
D. Sc. (Chemistry)
Belarus
D. Sc. (Chemistry)
V. I. Dolgopalets
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Ph. D. (Chemistry), Leading researcher
5/2, Kuprevich Str., 220141, Minsk
Yu. G. Charnou
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Ph. D. (Chemistry), Leading researcher
5/2, Kuprevich Str., 220141, Minsk
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