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

• Published in: Organic & biomolecular chemistry Vol. 21; no. 1; pp. 269 - 28
• Main Authors: Zheng, Jing, Gu, Hong, Chen, Qinfang, Yang, Weiran
• Format: Journal Article
• Published: 08.03.2023
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d3ob00087g

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. 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.