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. Issue 10 (20th February 2023)

• Record Type: Journal Article
• Authors: Zheng, Jing; Gu, Hong; Chen, Qinfang; Yang, Weiran
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 10(2023)
• Page Start: 2069
• Page End: 2080
• Publication Date: 2023-02-20
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d3ob00087g
• Languages: English
• ISSNs: 1477-0520

Abstract

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. 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.