チオモルホリン誘導体の研究(第2報) : 2-Alkyl-8-oxoperhydro-2H-1,4-thiazine-5-carboxylic Acidと塩化スルフリルとの反応

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The reaction of 2-alkyl-3-oxoperhydro-2H-1,4-thiazine-5-carboxylic acids (IVa-d) with sulfuryl chloride gave 2-alkyliden-3-oxoperhydro-2H-1,4-thiazine-5-carboxylic acids (VIa-d). Similarly, 2-alkyl-3-oxoperhydro-2H-1,4-thiazines (XVa-c) afforded 2-alkylidene derivatives (XVIIa-c). The reaction of 2,2-dimethyl-3-oxoperhydro-2H-1,4-thiazine-5-carboxylic acid (XIa) with sulfuryl chloride, on the other hand, gave 2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-thiazine-5-carboxylic acid (XIIIa) and 2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-thiazine (XIV), and the latter was also obtained by the reaction of 2,2-dimethyl-3-oxoperhydro-2H-1,4-thiazine (XVIII) with sulfuryl chloride. When 2-isopropyliden-3-oxoperhydro-2H-1,4-thiazine-5-carboxylic acid (VIb) was allowed to react with bromine, 1-(α-bromo) isopropyl-2-oxa-5-aza-7-thiabicyclo [2. 2. 2]-octa-3,6-dione (VIIIa) was obtained, presumably by the elimination of hydrogen bromide from the dibromide (VIIa) formed as an intermediate. VIIIb was also obtained by the reaction of VIb with sulfuryl chloride.
社団法人日本薬学会の論文
1971-02-25