ピリダジン誘導体(第12報) : 3,4-ジアザフェノチアジン誘導体の合成
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概要
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Application of 3,4,6-trichloropyridazine to N-substituted 2-aminobenzenethiol, obtained by alkaline decomposition of 3-substituted 2(3H)-benzothiazolinone, afforded 4-(N-substituted o-aminophenylthio)-3,6-dichloropyridazine whose treatment with a weak acid effected its Smiles rearrangement, followed by condensation-cyclization to 5-substituted 3-chloro-5H-benzo[b]pyridazino[4,3-e][1,4]thiazine, a derivative of 3,4-diazaphenothiazine. This was derived further to 5-substituted 3-methoxy derivative by the application of sodium methoxide. This process offers a general method for the synthesis of 3,4-diazaphenothiazines with a substituent in the nitrogen at 5-position. The compounds similarly obtained, 5-(2-dimethylaminoethyl)-3-methoxy-(XIV) and 3-chloro-5-(2-pyrolidinoethyl)-5H-benzo[b]pyridazino[4,3-e] [1,4]thiazine (XV), showed antihistamine action approximately equal to that of Antazoline.
- 公益社団法人日本薬学会の論文
- 1968-12-25
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関連論文
- ピリダジン誘導体(第12報) : 3,4-ジアザフェノチアジン誘導体の合成
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