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Synfacts 2010(5): 0520-0520
DOI: 10.1055/s-0029-1219721
DOI: 10.1055/s-0029-1219721
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Pot Synthesis of Benzisothiazoles from ortho-Mercaptoacylphenones
N. O. Devarie-Baez, M. Xian
Washington State University, Pullman, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201005/lookinside/thumbnails/10.1055-s-0029-1219721-1.jpg)
Significance
Reported is a one-pot synthesis of 3-substituted benzisothiazoles from ortho-mercaptoacylphenones by an in situ S-nitrosation procedure. The starting materials, readily prepared from thiosalicylic acids, are transformed into the unstable S-nitroso intermediates A, which upon treatment with EtPPh2 undergo an aza-Wittig reaction to produce the products in overall poor to very good yield. i-PentylONO proved to be the best oxidant for the formation of the S-nitroso intermediates without effecting the oxidation of EtPPh2.