One-pot synthesis of new A-ring fused steroidal pyridines

The preparation of pyridine rings fused to the 3,4-positions of the steroid nucleus is herein described. These new pyridine derivatives were prepared in good yields by the reaction of propargylamine with 17β-hydroxyandrost-4-en-3-one, 17α-methyl-17β-hydroxyandrost-4-en-3-one, 17β-hydroxyestr-4-en-3-one catalyzed by Cu(II). The structure of 17β-hydroxy-5-ene-androst-3-eno[3,4-b]pyridine was determined by X-ray analysis.