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, and1H and13C NMR spectroscopy of the initial and synthesized derivatives of 3-aza-D-homogonanes are presented and discussed.
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Institute of Bioorganic Chemistry, Academy of Sciences of Belarus', Minsk. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 959–965, July, 1995. Original article submitted May 6, 1995.
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Gulyakevich, O.V., Mikhal'chuk, A.L. & Akhrem, A.A. 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. Chem Heterocycl Compd 31, 835–840 (1995). https://doi.org/10.1007/BF01170745
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DOI: https://doi.org/10.1007/BF01170745