Parallel solution-phase synthesis of 4H-benzo[1,4]thiazin-3-one and 1,1-dioxo-1,4-dihydro-2H-1lambda6-benzo[1,4]thiazin-3-one derivatives from 1,5-difluoro-2,4-dinitrobenzene.

Zhanguo Wang, Yunyun Yuan, Yuyan Chen, Gangchun Sun, Xianghong Wu, Shengmei Zhang, Chunyan Han, Guanxing Wang, Li Li, Gang Liu

Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union of Medical College, 1 Xian Nong Tan Street, Beijing 100050, P. R. China.

Journal of combinatorial chemistry 2007 Jul-Aug

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This paper discusses the synthesis of privileged structures 4H-benzo[1,4]thiazin-3-one and 1,1-dioxo-1,4-dihydro-2H-1lambda6-benzo[1,4]thiazin-3-one derivatives in a parallel solution-phase manner using 1,5-difluoro-2,4-dinitrobenzene. Each scaffold possesses four diversity points. A cheap and efficient oxidant, urea-hydrogen peroxide (UHP), was applied for the introduction of the sulfone group. The intramolecular cyclization to 1,1-dioxo-1,4-dihydro-2H-1lambda6-benzo[1,4]thiazin-3-one was achieved by microwave assistance or the use of an inorganic base.

Citation

Zhanguo Wang, Yunyun Yuan, Yuyan Chen, Gangchun Sun, Xianghong Wu, Shengmei Zhang, Chunyan Han, Guanxing Wang, Li Li, Gang Liu. Parallel solution-phase synthesis of 4H-benzo[1,4]thiazin-3-one and 1,1-dioxo-1,4-dihydro-2H-1lambda6-benzo[1,4]thiazin-3-one derivatives from 1,5-difluoro-2,4-dinitrobenzene. Journal of combinatorial chemistry. 2007 Jul-Aug;9(4):652-60