Conversion of Dipyridazino [4,5-b : 4', 5'-e] [1,4] thiazines into Dipyridazino [4,5-b : 4', 5'-d] pyrroles through a Base-Induced Extrusion of Sulfur

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概要

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• A novel ring contraction for the conversion of 2,7-disubstituted 10H-dipyridazino [4,5-b : 4', 5'-e] [1,4] thiazine-1,6-(2H, 7H)-diones (4'a-c) into the corresponding 2,6-disubstituted 9H-dipyridazino [4,5-b : 4', 5'-d] pyrrole-1,5 (2H, 6H)-diones (7'a-c), through a base-induced extrusion of sulfur, is described. Heating of 4'a-c in dimethylformamide in the presence of potassium carbonate smoothly afforded 7'a-c, respectively, in good yields, although neither 2,8-dimethyl-10H-dipyridazino [4,5-b : 4', 5'-e] [1,4] thiazine-1,9 (2H, 8H)-dione (5'a), nor 3,7-dimethyl-10H-dipyridazino [4,5-b : 4', 5'-e] [1,4] thiazine-4,6 (3H, 7H)-dione (6'a) was susceptible to similar reaction conditions. The mechanism of the ring contraction, which may involve an intermediate (anion, C^-) containing a thiirane ring, is also discussed.

• 公益社団法人日本薬学会の論文
• 1984-04-25

著者

• 長島 弘

  Gifu Pharmaceutical University

• 小田 博久

  Gifu Pharmaceutical University

• 鍛冶 健司

  Gifu Pharmaceutical University

• 鍛治 健司

  Gifu College of Pharmacy

• 鍛治 健司

  岐阜薬科大学

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