STEROIDS: PART I. THE SYNTHESIS OF SOME HETEROCYCLIC STEROID DERIVATIVES

Abstract

Cyanoacetamide reacted with 3β-hydroxy-16-hydroxymethylene-5-androsten-17-one to form 1-cyano-2-hydroxy-2(16′-3′β-hydroxy-17′-oxo-5′-androstenyl) propionamide or 3-cyano-4,5-dehydro-6-hydroxy-5,6(16′,17′-3′β-hydroxy-5′-androstenyl)-2-piperidone depending on whether a catalytic or a molecular amount of piperidine was used as the basic condensing agent. Carboxamidoacetamidine, and acetamidine hydrochlorides, were condensed with the sodium salt of 3β-hydroxy-16-hydroxymethylene-5-androsten-17-one, and 3β-chloro-16-chloromethylene-5-androsten-17-one yielding 2-amino-3-carboxamido-5,6(16′, 17′-3′β-hydroxy-5′-androstenyl) pyridine and 2-methyl-5,6(16′,17′-3′β-chloro-5′-androstenyl) pyrimidine respectively.