Studies on Condensed Heterocyclic Isoquinolone Derivatives. III. A Novel Oxidative Rearrangement of 11-Methyl-6-oxo-3,4-dihydro-2H, 6H-1,3-thiazino [3,2-b] isoquinoline

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概要

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• The reaction of 11-methyl-6-oxo-3,4-dihydro-2H, 6H-1,3-thiazino [3,2-b] isoquinoline (I) or the corresponding sulfone (II) with hydrogen peroxide led to a ring enlargement reaction to give a β-keto-sulfone, 1,6-methano-1-methyl-7,12-dioxo-4,5,7-trihydro-1H, 3H-benzo [g]-1,5-thiazonine 2,2-dioxide (III), which was further converted into an enolsulfone, 12-methyl-7-oxo-3H, 7H-4,5-dihydro-2,1,4-oxathiazepino [4,3-b] isoquinoline 2,2-dioxide (VI), by thermal rearrangement. These ring enlargement and thermal rearrangement reactions involve intramolecular migration of the sulfonyl group. On treatment with sodium hydroxide, compound III gave 5-methyl-3,3a-dihydro-2H, 5H-[2] benzothio-pyrano [4,3-b] pyrrole 4,4-dioxide (VIII), presumably by hydrolysis and intramolecular condensation. Reaction of compound I with chlorine in the presence of water gave 3-(4-chloro-4-methyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl) propanesulfonyl chloride (X) by ring opening, while compound II gave an additicn product, 11,11a-dichloro-11-methyl-6-oxo-3,4,11,11a-tetrahydro-2H, 6H-1,3-thiazino [3,2-b] isoquinoline 1,1-dioxide (XIII), as the major product.

• 公益社団法人日本薬学会の論文
• 1980-04-25

著者

• 村上 増雄

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 磯村 八州男

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 伊藤 徳樹

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 久保 一夫

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.

• 久保 一夫

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 磯村 八州男

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 伊藤 徳樹

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 磯村 八州男

  山之内製薬

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