THERMAL INTRAMOLECULAR CYCLIZATION OF 2-ETHYNYLPYRIDINE N-YLIDES TO INDOLIZINES AND CYCLAZINES

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概要

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• Treatment of 2-ethynyl-1-phenacylpyridinium bromides (1a-c), prepared from 2-ethynylpyridines and phenacyl bromide, with a base, DBU, in refluxing benzene gave 3-benzoylindolizines (2), whereas heating the salts (1) in refluxing acetic acid afforded 1-benzoylindolizines (3). Upon similar treatment with the base, 2-ethynyl-6-methyl-1-phenacyl-pyridinium bromides (10a-c) gave 2-phenylcycl [3. 2. 2] azines (12), together with 3-benzoylindolizines (11). However, the reaction of 6-amino-2-ethynylpyridines (17a-c) with phenacyl bromide resulted in the formation of 1-azaindolizines (18), which were treated with the base to give 1-azacycl [3. 2. 2] azines (19). The mechanisms for these intramolecular cyclization via pyridine N-ylide intermediates are discussed.

• 公益社団法人日本薬学会の論文
• 1984-11-25

著者

• 土屋 隆

  School of Pharmacy, Hokuriku University

• 指田 春喜

  School of Pharmacy, Hokuriku University

• 指田 春喜

  北陸大学薬学部

• 指田 春喜

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 土屋 隆

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 加藤 昌信

  School of Pharmacy, Hokuriku University

• 加藤 昌信

  School Of Pharmacy Hokuriku University

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