Access to thiazoline and spiro[indoline-3,3′-thiophene] scaffolds via a formal [3 + 2] annulation reaction of crotonate-derived sulfur ylides and β-ketothioamides?

Organic & Biomolecular Chemistry Pub Date: 2023-02-01 DOI: 10.1039/D3OB00087G

Abstract

A formal [3 + 2] annulation reaction of crotonate-derived sulfur ylides and β-ketothioamides (KTAs) was successfully developed to produce good-to-excellent yields of thiazoline and spiro[indoline-3,3′-thiophene] scaffolds. This transformation is a powerful tool for the synthesis of thiazoline and spiro[indoline-3,3′-thiophene] scaffolds due to its mild reaction conditions, easily accessible starting materials, and broad substrate scope. A large-scale reaction was carried out to ensure the practical applicability of this methodology. Finally, the plausible mechanistic pathway of the developed methodology was investigated.

Graphical abstract: Access to thiazoline and spiro[indoline-3,3′-thiophene] scaffolds via a formal [3 + 2] annulation reaction of crotonate-derived sulfur ylides and β-ketothioamides
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