Investigations on Steroids. XI. Synthesis of Steroidal Oxazole, Imidazole, and Triazole

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概要

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• Steroidal oxazoles, imidazoles, and triazoles were synthesized for biological studies. 2α-Acetoxy-or 2α-bromo-3-ketones of androstane and cholestane series were converted into 2'-methylsteroidal [3,2-d] oxazoles (III) by reaction with ammonium acetate. Reductive acetylation of 2-hydroxyimino-3-oxo steroids (V) gave 2α-acetamido-3-ketones (VI) which were cyclized by the use of sulfuric acid to 2'-methyl-steroidal [2,3-d] oxazoles (XI). 2'-methyl-steroidal [2,3-d] imidazoles (XII) were prepared from VI by reaction with ammonium acetate. 2α-Amino-3-ketone hydrochlorides, obtained by catalytic hydrogenation of V, were converted by reaction with thiocyanate into steroidal [2,3-d] imidazoline-2'-thiones which were desulfurized to afford imidazoles (XIV). Androst-4-eno[2,3-d]-triazoles (XX) were prepared from the 2-acetoxymethylene-3-ketone via the 2-hydroxyimino-3-one hydrazone by application of the established procedures. The ORD (and CD) data of VI and the corresponding 3β-alcohol (VIIId) are presented.

• 公益社団法人日本薬学会の論文
• 1968-08-25

著者

• 小畑 和永

  Central Research Laboratory Daiichi Seiyaku Co. Ltd.

• 越 克己

  Central Research Laboratory, Daiichi Seiyaku Co., Ltd.

• 太田 元告

  Central Research Laboratory, Daiichi Seiyaku Co., Ltd.

• 越 克己

  Central Research Laboratory Daiichi Seiyaku Co. Ltd.

• 太田 元告

  Central Research Laboratory Daiichi Seiyaku Co. Ltd.

関連論文

• Investigations on Steroids.VIII.Synthesis of Steroidal [2,3-c] furazans of Pregnane Series
• The Synthesis of 2,3-Dimethoxy-5-methyl-p-benzoquinone and Related Compounds
• An Improved Synthesis of 5-Methyl-2,3-dimethoxy-p-benzoquinone
• Investigations on Steroids. XI. Synthesis of Steroidal Oxazole, Imidazole, and Triazole

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