7α,17α-二甲基-17β-羟基雄甾-4-烯-3酮的若干A环骈杂环衍生物的合成

SYNTHESIS OF SOME RING A FUSED HETEROCYCLIC 7α, 17α-DIMETHYL-17β-HYDROXYANDROST-4-EN-3-ONE

摘要: 将7α-甲基引进甲基睾丸素后,经甲酰化反应制得2-羟次甲基衍生物(Ⅳ),再先后转变为单肟(Ⅴ)、双肟(Ⅵ),环合得70,17α-二甲基-17β-羟基-雄甾-4-烯骈2,3-c呋咱(Ⅶ)。也可使(Ⅳ)与水合肼或盐酸羟胺作用,分别制得相应的雄甾-4-烯骈3,2-c吡唑(Ⅷ)及雄甾2,4-二烯骈2,3-d异(口恶)唑(Ⅸ)。在酸性反应条件下合成(Ⅸ)时,还分离出它的重排脱水产物7α,17α,17β-三甲基雄甾-2,4,13-三烯骈2,3-d异(口恶)唑(Ⅹ)。

Abstract: In the search of new anabolic and hypolipemic steroids, 7α, 17α-dimethyl-17β-hydroxyandrost-4-eno--2,3-C furazan(Ⅶ) and corresponding -3, 2-C pyrazole(Ⅷ), and 7α, 17α-dimethyl-17βhydroxy androst-2, 4-dien 2, 3-d isoxazol(Ⅸ) were synthesized from the major intermediate 2-hydroxymethylene-7α, 17α-dimethyl-17β hydroxyandrost-4-en-3-one(Ⅳ).On synthesizing(Ⅸ) under acidic condition, its Wagner-Meerwein rearrangement product 7α, 17α, 17β-trimethylandrost-2, 4, 13-trien 2, 3-d isoxazol(Ⅹ) was also obtained.