Synthesis of 3-Substituted Aryl[4,5]isothiazoles through an All-Heteroatom Wittig-Equivalent Process
- Fanghui Xu ,
- Yuan Chen ,
- Erkang Fan , and
- Zhihua Sun
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† College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China
‡ Department of Biochemistry, University of Washington, 1705 NE Pacific Street, Seattle, Washington 98195, United States
*E-mail: [email protected]
Abstract
Extending the previous use of tert-butyl sulfoxide as the sulfinyl source, intramolecular sulfinylation of sulfonamides was successfully performed. The resulting sulfinimides were not isolated and instead were believed to go through an all-heteroatom Wittig-equivalent process to eventually afford aryl[4,5]isothiazoles in high yields.
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- Boram Seo, Ya Gob Kim, and Phil Ho Lee . Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Nitriles. Organic Letters 2016, 18 (19) , 5050-5053. https://doi.org/10.1021/acs.orglett.6b02499
- Anirban Bera, Prasanta Patra, Abulkalam Azad, Sk Asraf Ali, Susanta Kumar Manna, Amit Saha, Shubhankar Samanta. Neat synthesis of isothiazole compounds, and studies on their synthetic applications and photophysical properties. New Journal of Chemistry 2022, 46 (24) , 11685-11694. https://doi.org/10.1039/D2NJ01962K
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- V.I. Potkin, A.V. Kletskov, F.I. Zubkov. Isothiazoles. 2022, 482-529. https://doi.org/10.1016/B978-0-12-818655-8.00127-X
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- Dominic C. Castell, Ntlama Lesotho, Varvara I. Nikolayenko, Gareth E. Arnott. Inherently Chiral Calix[4]arenes: A Chiral Sulfoxide as an Ortholithiation Director. European Journal of Organic Chemistry 2017, 2017 (29) , 4328-4333. https://doi.org/10.1002/ejoc.201700701
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