Collect. Czech. Chem. Commun.
1998, 63, 1589-1596
https://doi.org/10.1135/cccc19981589
Reduction of 2-Nitro-5α-cholestan-3-one, Its Enol Tautomer and 2-Nitro-5α-cholest-2-en-3-amine Derivatives. Synthesis of Bis-Steroidal Pyrazines
Jacek W. Morzyckia, Agnieszka Gryszkiewicza, Zenon Lotowskia and Wojciech J. Szczepekb
a Institute of Chemistry, University of Warsaw, Białystok Branch, Pilsudskiego 11/4, 15-443 Białystok, Poland
b Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warszawa, Poland
Abstract
Reduction of 2α-nitro-5α-cholestan-3-one (4), its enol tautomer (3a) and 3-acetylamino-2-nitro-5α-cholest-2-ene (2) was studied. The latter compound was reduced with zinc in acetic acid to 3β-acetylamino-5α-cholestan-2-one (8). The similar reaction of 3a or 4 led to 2α-amino-5α-cholestan-3-one (11a), that may be trapped as N-formyl derivative. When crude 11a was subjected to air oxidation, pyrazino[2',3':2,3;5',6':2,3]bis(5α-cholestane) (9) was obtained.
Keywords: α-Nitro ketones; α-Amino ketones; Zinc reduction; Bis-steroidal pyrazines; Steroids; Alkaloids; Cephalostatin.
