Synthesis of Steroidal Diazolidinone, Diazolidinthione and Diazoles: Reaction of Steroidal Dibromoketones With Nucleophilic Nitrogen

Abstract

Reaction of 5,6β-dibromo-5α-cholestan-3-one 1 with thiourea, urea and guanidine hydrochloride provided 3-hydroxycholest-3-eno [5α,6α-d] 1',3'-diazolidin-2'-thione 2, 3-hydroxycholest-3-eno [5α,6α-d] 1',3'-diazolidin-2'-one 3 and 3-hydroxycholest-3-eno [5α,6α-d] 2'-amino-1',3'-diazole 4 respectively. The structures of these products have been established on the basis of their elemental analysis and spectral data (IR, 1 H NMR and MASS).