以1,5-二氟-2,4-二硝基苯为原料平行溶液相合成4H-苯并[1,4]噻嗪-3-酮和1,1-二氧代-1,4-二氢-2H-1λ⁶-苯并[1,4]噻嗪-3-酮衍生物

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.

作者信息

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

机构信息

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

出版信息

J Comb Chem. 2007 Jul-Aug;9(4):652-60. doi: 10.1021/cc0601276. Epub 2007 May 16.

DOI:10.1021/cc0601276

PMID:17503786

Abstract

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.

摘要

本文讨论了以1,5-二氟-2,4-二硝基苯为原料，采用平行溶液相法合成具有特殊结构的4H-苯并[1,4]噻嗪-3-酮和1,1-二氧代-1,4-二氢-2H-1λ6-苯并[1,4]噻嗪-3-酮衍生物。每个骨架都有四个多样性位点。使用廉价高效的氧化剂尿素过氧化氢（UHP）引入砜基。通过微波辅助或使用无机碱实现分子内环化生成1,1-二氧代-1,4-二氢-2H-1λ6-苯并[1,4]噻嗪-3-酮。