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Synthesis of Isothiazoles through N‑Propargylsulfinylamide: TFA-Promoted Sulfinyl Group-Involved Intramolecular Cyclization

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journal contribution
posted on 23.08.2021, 13:04 by Ziyi Li, Nana Wang, Jiang Liu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han
A new reactivity mode of tert-butanesulfinamide has been developed, which proceeds through C–S and O–S bond cleavage of N-propargyl tert-butanesulfinylamide allowing rapid assembly of poly functionalized isothiazoles. This intramolecular cyclization reaction could be conducted under mild and convenient conditions and tolerates several fluoroalkyl and substituted phenyl groups with good chemical yields. This reaction not only represents a new reactivity of tert-butanesulfinamide but also provides an easy strategy for the synthesis of isothiazoles.