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.
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.
Wang
Zhanguo
Z
Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union of Medical College, 1 Xian Nong Tan Street, Beijing 100050, P. R. China.
Yuan
Yunyun
Y
Chen
Yuyan
Y
Sun
Gangchun
G
Wu
Xianghong
X
Zhang
Shengmei
S
Han
Chunyan
C
Wang
Guanxing
G
Li
Li
L
Liu
Gang
G
D000588:Amines / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D004139:Dinitrofluorobenzene / Q000031:analogs & derivatives* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry; D012996:Solutions; D013843:Thiazines / Q000138:chemical synthesis / Q000737:chemistry*
D000588:Amines; D010879:Piperazines; D012996:Solutions; D013843:Thiazines; D000077489:Piperazine; D006859:Hydrogen; D004139:Dinitrofluorobenzene; C002041:1,5-difluoro-2,4-dinitrobenzene; D001554:Benzene; D010100:Oxygen