Thermal Rearrangements of Cyclic Amine Ylides. IV. Rearrangement of β, γ-Unsaturated 1-Alkylpiperidine N-Oxides : Formation of 1,2-Oxazepine Derivatives

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概要

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• The thermolysis of 1-methyl-2-vinylpiperidine N-oxide (13) resulted in Meisenheimer [1,2] rearrangement to give the hexahydro-1,2-oxazepine (23) and no [2,3]-sigmatropic rearrangement product (24). Similarly, the 1-methyl-1,2,5,6-tetrahydropyridine N-oxides (15), on heating, gave only the tetrahydro-1,2-oxazepines (26,27), together with the Hofmann-type elimination products (28). The thermolysis of 1-benzyl-2-phenyl-(20a) and 1-benzyl-2-vinyl-piperidine N-oxide (20b) afforded the corresponding 1-benzyloxypiperidines (32) as well as the 1,2-oxazepines (31). These results are different from those observed for open-chain allylamine N-oxides and 1-alkyl-2-vinylpiperidine N-imides and N-ylides, which are known to undergo only [2,3]-sigmatropic rearrangement.

• 公益社団法人日本薬学会の論文
• 1984-10-25

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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