Stereoselective Syntheses of cis- and trans-2-Alkylamino-1,2,3,4-tetrahydro-1-naphthalenols by Acid-catalyzed Ring Opening of 1,2-N-Alkylimino-1,2,3,4-tetrahydronaphthalenes

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概要

• 論文の詳細を見る

• 5- or 7-Substituted cis- and trans-2-tert-butylamino-6-hydroxy-1,2,3,4-tetrahydro-1-naphthalenols (cis-29-cis-32) and (trans-30-trans-35) were synthesized from 1,2-N-tertbutylimino derivatives. Acid-catalyzed ring opening of 1,2-alkylimino-1,2,3,4-tetrahydronaphthalene derivatives (1-11) produced a mixture of cis- and trans-2-alkylamino-1,2,3,4-tetrahydro-1-naphthalenol derivatives whose ratio was markedly affected by substituents on the benzene ring. Stereoselective ring opening of the aziridines and interconversion of cis- and trans-2-alkylamino-1-tetralols via 1-hydroxysulfonyloxy intermediates were described. The reaction mechanism of acid-catalyzed ring opening of the aziridines and hydrolysis of 2-alkylamino-1-hydroxysulfonyloxy-1,2,3,4-tetrahydronaphthalene derivatives is also discussed.

• 公益社団法人日本薬学会の論文
• 1978-02-25

著者

• 杉原 弘貞

  Central Research Division, Takeda Chemical Industries, Ltd.,

• 鵜川 清

  Central Research Division, Takeda Chemical Ind., Ltd.,

• 三宅 昭夫

  Central Research Division, Takeda Chemical Industries, Ltd.

• 三野 安

  Central Research Division, Takeda Chemical Industries, Ltd.

• 三宅 昭夫

  Central Research Division Takeda Chemical Industries Ltd.

• 杉原 弘貞

  Pharamaceutical Research Laboratories I Pharmaceutical Research Division Takeda Chemical Industries

• 杉原 弘貞

  Central Research Division Takeda Chemical Industries. Ltd.

• 鵜川 清

  Resarch & Development Division Takeda Chemical Industries Ltd.

• 三野 安

  Central Research Division Takeda Chemical Industries Ltd.

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