Facile Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxides and Related Reaction with 1,3-Diiodo-5,5-dimethylhydantoin under Photochemical Conditions

作者：Moroda Atsush; Furuyama Shusuke; Togo Hideo^*

来源：Synlett, 2009, 2009(8): 1336-1340.

DOI：10.1055/s-0028-1216725

• 3,4-dihydro-2,1-benzothiazine 2,2-dioxide
• 1,3-diiodo-5,5-dimethylhydantoin
• 1,2,3,4-tetrahydroquinoline
• tungsten lamp
• irradiation
• sulfonamidyl radical

3,4-Dihydro-2,1-benzothiazine 2,2-dioxides were easily obtained in good yields by the reaction of N-methyl 2-arylethane-sulfonamides with 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation with a tungsten lamp. When N-benzyl 2-phenylethane-sulfonamide was treated with DIH under the same conditions, the corresponding N-benzyl 3,4-dihydro-2,1-benzothiazine 2,2-dioxide was obtained in good yield, and the N-benzyl group was easily removed by the treatment with hydrogen in the presence of Pd(OH)(2). On the other hand, treatment of N-3-arylpropyl trifluoromethane-sulfonamides with DIH under irradiation with a tungsten lamp provided corresponding N-trifluoromethanesulfonyl-1,2,3,4-tetrahydroquinolines in good yields.

• 出版日期2009-5-15