Dithioester-enabled chemodivergent synthesis of acids, amides and isothiazoles via CC bond cleavage and CO/CN/CS bond formations under metal- and catalyst-free conditions. Issue 25 (21st June 2017)

• Record Type: Journal Article
• Authors: Soni, Sonam; Koley, Suvajit; Singh, Maya Shankar
• Is Part Of: Tetrahedron letters. Volume 58:Issue 25(2017)
• Page Start: 2512
• Page End: 2516
• Publication Date: 2017-06-21
• Subjects: β-Ketodithioesters -- Amides -- Isothiazoles -- Acids -- Vitamin B3; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.05.064
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Base-controlled chemoselective formation of acids & amides from β-ketodithioesters. One-pot, metal- and catalyst-free conditions. Ample substrate scope and broad functional group tolerance. More importantly, an easy route for the formation of vitamin B3 is reported. Abstract: An operationally simple and user-friendly process to access privileged scaffolds such as acids, amides and isothiazoles has been devised employing β-ketodithioesters for the first time. Remarkably, the new protocol involves combination of CC bond cleavage and CO/CN/NS bond formations in one-pot. Aqueous ammonia led to the formation of skeletally distinct amide and isothiazole, whereas aqueous NaOH enabled the formation of aromatic acid near quantitative yield. This practical approach, which can dramatically streamline the synthesis of simple molecules, is highly chemoselective, cost-effective, amenable to gram scale, insensitive to moisture as well as bears high functional group compatibility.