Studies on the Smiles Rearrangement. XII. Synthesis and Structural Assignment of Two Isomeric N-Phenyl-2,3-diazaphenothiazinones

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概要

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• Alkaline treatment of 5-(ο-acetamidophenylthion)-4-chloro-2-phenyl-3(2H)-pyridazinone (II) resulted in the exclusinve formation of 3-phenyl-10H-benzo(b) pyridazino[4,5-e][1,4]thiazine-4-(3H)-one (III) via Smiles rearrangement. Isomeric 2-phenyl-10H-benzo[b]pyridazino[4,5-e][1,4]thiazine-1(2H)-one (IV) was obtained preferentially upon treatment of deacetyl derivative (I) with acid together with II. The structures of III and IV were established both by comparison of their chemical properties and by an unequivocal synthesis of IV. A novel ring contraction of IV to spiro(2-phenyl-4(3H)-pyrazolone-3,2'-benzothiazoline) (XIV) was observed.

• 公益社団法人日本薬学会の論文
• 1973-02-25

著者

• 牧 敬文

  Gifu College Of Pharmacy

• 高谷 昌弘

  浜理薬品工業(株)研究所

• 鈴木 巳喜男

  Gifu College of Pharmacy

• 鈴木 巳喜男

  岐阜薬科大学一般化学研究室

• 豊田 修

  Gifu College of Pharmacy

• 高谷 昌弘

  Pharmacological Laboratory, Morishita Pharmaceutical Co., Ltd.

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