チオモルホリン誘導体の研究(第1報) : 2-置換-3-oxoperhydro-2H-1,4-thiazine-5-carboxylic Acidの合成と, 塩化チオニルおよび塩化スルフリルとの反応

概要

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The reactions of several alkyl DL-α-bromoalkylcarboxylate (III) with L-cysteine disodium salt in liquid ammonia afforded 2-substituted-3-oxoperhydro-2H-1,4-thiazine-5-carboxylic acids (IV). When 2-phenyl-3-oxoperhydro-2H-1,4-thiazine-5-carboxylic acid (IVc) was reacted with thionyl chloride containing sulfuryl chloride at room temperature, white crystal of 1-phenyl-2-oxa-5-aza-7-thiabicyc1o [2.2.2] octa-3,6-dione (VII) and syrupy oil of 2-phenyl-3-oxoperhydro-2H-1,4-thiazine-5-carbonyl chloride (VIII_2) were obtained. The latter was confirmed by the conversion to the amide (IX_2), which was obtained by reaction with aqueous ammonia. The production of the lactone (VII) was attributable to the result of the dehydrocyclization where using sulfuryl chloride and thionyl chloride. The relationship between the yields of the lactone (VII) and the ratios of sulfuryl chloride-thionyl chloride was investigated.
社団法人日本薬学会の論文
1970-05-25