Steroids and related studies. Part XVIII. 3-Aza-A-homo-4a-eno[3,4-d]tetrazole steroid analogues

Abstract

Treatment of (25R)-spirost-4-en-3-one with excess of hydrazoic acid in the presence of boron trifluoride gives (25R)-3-aza-A-homospirost-4a-eno[3,4-d]tetrazole. The latter has been degraded to 3-aza-A-homopregna-4a,16-dieno[3,4-d]tetrazol-20-one, the 16α,17α-epoxide of which yielded the 17α-16β-chloro-, bromo-, and thiocyanato-derivatives. The oxime of 3-aza-A-homopregna-4a,16-dieno[3,4-d]tetrazol-20-one, on rearrangement and hydrolysis, gave 3-aza-A-homoandrost-4a-eno[3,4-d]tetrazol-17-one.