Isothiazole Construction by Metal-Free Reactions of Thioamides with Iminoiodinanes and Their Photophysical Properties
- 27 February 2025
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 90 (10) , 3590-3602
Abstract
Metal-free reactions of thioacetamide derivatives with N-sulfonyliminoiodinane, affording isothiazoles under mild conditions, are described. 2-Substituted thioacetamides modified with an enamine moiety undergo reactions with iminoiodinane to form 4,5-disubstituted isothiazoles in 72-93% yields. Reactions of (het)arylidene-substituted 2-thioacetamides and iminoiodinane with subsequent one-pot oxidation of the formed sulfonylisothiazolines afford 3,4,5-trisubstituted isothiazoles in 44-96% yields. A scale-up synthesis of the developed methods was performed. The photophysical properties of the new isothiazoles were investigated, and UV- or blue-light-shifted fluorescence has been detected (QY up to 11%).Keywords
Funding Information
- Russian Science Foundation (23-13-00248)
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