3-Hydroxypyrroles. II. The Reaction of 4,5-Unsubstituted Alkyl 3-Hydroxypyrrole-2-carboxylates with Some Electrophiles

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概要

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• The reaction of alkyl 3-hydroxypyrrole-2-carboxylates (1) with some electrophiles was investigated. The alkylation of 1c occurred at the O and C-2 position as in the case of usual β-keto esters. An N-substituted 3-hydroxypyrrole-2-carboxylate (1e) reacted at the 2-position upon the Michael reaction. In addition to the C-2 adduct (9), an unexpected 2,2-bis-adduct (10) was concurrently obtained possibly via the ketonic cleavage of the mono-adduct (9) followed by the second addition of acrylate. The N-unsubstituted one (1b) gave a mono-adduct at C-2 (12) and a bis-adduct at C-2 and N (13). Upon bromination, 1c reacted at the 4-and 5-position, not at the 2-position ; namely 1c reacted with bromine as an enamine or a pyrrole, and not as a β-keto ester. The Mannich reaction occurred rapidly and selectively at the 4-position, and the 4-bromo derivative (15) reacted preferentially at the 5-position. In the cyanation of the quarternary salts of the Mannich bases, a dimer (23), a trimer (24) and a dicyano compound (26) were obtained in addition to the expected cyanides (22,25).

• 社団法人日本薬学会の論文
• 1978-11-25

著者

• 山田 和代

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 徹明

  Faculty of Pharmaceutical Sciences, Osaka University

• 田中 徹明

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 百瀬 雄章

  富山医薬大・薬

• 百瀬 雄章

  (present Address)faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Osaka University

• 横田 卓士

  Faculty of Pharmaceutical Sciences, Osaka University

• 永本 典生

  Faculty of Pharmaceutical Sciences, Osaka University

• 横田 卓士

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 永本 典生

  Research Laboratories, Dainippon Pharmaceutical Co., Ltd.

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