Thermal Rearrangements of Cyclic Amine Ylides. II. Ring-expansion of 4- and 6-Vinyl-1,2,5,6-tetrahydropyridine and 2-Vinylpiperidine N-Imides

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概要

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• The thermolysis of the 4-vinyl-1,2,5,6-tetrahydropyridine N-imide (13a) resulted in both [1,2-]- and [2,3]-sigmatropic rearrangements to give the tetrahydro-1,2-diazepine (18) and the 3,3-divinyltetrahydropyrazole (19), respectively ; this reaction mechanism was confirmed by a deuterium-labelling experiment. In contrast, the thermolysis of both 6-vinyl-1,2,5,6-tetrahydropyridine N-imide (13b) and 2-vinylpiperidine N-imide (17) resulted in only [2,3] rearrangement with the vinyl group to give nine-membered ring products, the tetrahydro- (21) and the hexahydro-1,2-diazonine (25), respectively. The starting vinyltetrahydropyridine N-imides (13a, b) were prepared from the corresponding vinylpyridines (10a, b), and 2-vinylpiperidine N-imide (17) was prepared from 1-ethoxycarbonyl-2-vinylpiperidine (14).

• 公益社団法人日本薬学会の論文
• 1981-07-25

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

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