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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.