Sigmatropic Rearrangement of Cyclic α-Vinyl Sulfonium Imides : Formation of Thiazocine, Thiazonine, and Thiazecine Derivatives

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概要

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• Thermolysis of the cyclic α-vinyl sulfonium p-toluenesulfonylimides (6a-c), prepared from 2-vinylthiolane (5a), 2-vinylthiane (5b), and 2-vinylthiepane (5c) by treatment with chloramine T, resulted in [2,3]-sigmatropic rearrangement with ring-expansion to give the 1,2-thiazocine (7a), 1,2-thiazonine (7b), and 1,2-thiazecine derivative (7c), respectively. Similarly, the 1,2-benzothiazonine (17) and the 3,4-benzothiazonine (18) were obtained from 2-vinylthiochroman (13) and 1-vinylisothiochroman (14) via the imides (15 and 16), respectively. The stereochemistry of the rearrangement is discussed.

• 公益社団法人日本薬学会の論文
• 1986-09-25

著者

• 土屋 隆

  Faculty of Pharmaceutical Sciences, Hokuriku University

• 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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