Investigations on Steroids. I. Synthesis of Androstano [3, 2-b] pyridine.

Abstract

Syntheses of 17β-hydroxyandrostano [3, 2-b] pyridine (XXIVa) and related compounds were described. Condensation of 2-hydroxymethylene-3-oxo androstane derivatives with cyanoacetamide or its analogs afforded 5', 6'-disubstituted androstano [3, 2-b] pyridines which were converted into pyridine-6'(1'H)-thiones (XVII). Desulfurization of XVII gave 5', 6'-unsubstituted androstano [3, 2-b] pyridines (XXIV).