AI Article Synopsis
- A new cyclization reaction has been developed combining O-acyl oximes, silyl enol ethers, and elemental sulfur, producing compounds like 2-aroylnaphthothiazoles and 2-aroylbenzothienothiazoles.
- The reaction likely proceeds via a radical mechanism with key intermediates such as S⋅ and an iminosulfur radical, leading to products through a series of steps including nucleophilic substitution and intramolecular cyclization.
- The resulting products show promising fluorescence properties, suggesting they could have useful applications in functional materials.
Article Abstract
A three-component cyclization reaction of O-acyl oximes, silyl enol ethers and elemental sulfur has been developed, in which silyl enol ether acts as a C1 synthon to participate in cyclization reaction and build a series of 2-aroylnaphthothiazoles and 2-aroylbenzothienothiazoles. The preliminary exploration of the reaction mechanism indicated that this transformation probably proceeded through a radical process, involving S⋅ as a key intermediate, enabling subsequent nucleophilic substitution with O-acyl oximes to afford iminosulfur radical, which undergoes 1,3-H shift to yield sulfur-centered radical intermediate. And then this intermediate undergoes radical addition with silyl enol ether, leading to the formation of the titled products through intramolecular cyclization and oxidation. Moreover, the products obtained exhibit favorable fluorescence properties, which indicates their potential application as functional materials.
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| http://dx.doi.org/10.1002/chem.202402976 | DOI Listing |
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