Categories: Synthesis of N-Heterocycles, Synthesis of S-Heterocycles > benzo-fused N-Heterocycles, benzo-fused S-Heterocycles >
Synthesis of benzisothiazoles
Recent Literature
Starting from readily available o-mercaptoacylphenones, a mild S-nitrosation
and a subsequent intramolecular aza-Wittig reaction lead to the construction of
3-substituted benzisothiazoles.
N. O. Devarie-Baez, M. Xian, Org. Lett., 2010,
12, 752-754.
An acid-catalyzed thermolysis of a tert-butyl sulfoxide enables a simple
synthesis of 3-substituted aryl[4,5]isothiazoles. Substituted aryl rings of varying
electronic properties afford
aryl[4,5]isothiazoles in high yields in the presence of a catalytic amount of p-toluenesulfonic
acid in toluene.
H. Yuan, Z. Sun, Synlett, 2019,
30,
1904-1908.
tert-Butyl sulfoxides can be used as sulfinyl sources in an
intramolecular sulfinylation of sulfonamides followed by an all-heteroatom
Wittig-equivalent process to afford aryl[4,5]isothiazoles in high yields.
F. Xu, Y. Chen, E. Fan, Z. Sun, Org. Lett.,
2016, 18, 2777-2779.
A CuBr2-catalyzed annulation of 2-bromo-N-arylbenzimidamides with selenium/sulfur
powder provides benzo[d]isoselenazoles and benzo[d]isothiazoles in
good yields. This method offers good
substrate scope and functional group tolerance. Furthermore, (phenyl)amino-substituted
products could be converted into N-aryl indoles via rhodiumIII-catalyzed
ortho
C-H activation of the N-phenyl ring.
Q. Wang, F. Xiao, Z. Huang, G. Mao, G.-J. Deng, J. Org. Chem., 2023, 88,
1963-1976.