Acid-promoted metal-free synthesis of 3-ketoquinolines from amines, enaminones and DMSO. Issue 31 (1st August 2019)

• Record Type: Journal Article
• Authors: Jiang, Tao-Shan; Zhou, Yuhui; Dai, Long; Liu, Xiaojun; Zhang, Xiuli
• Is Part Of: Tetrahedron letters. Volume 60:Issue 31(2019)
• Page Start: 2078
• Page End: 2083
• Publication Date: 2019-08-01
• Subjects: Enaminones -- DMSO -- One carbon synthon -- 3-Ketoquinolines; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.07.010
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A metal-free synthesis of 3-ketoquinolines directly from anilines, enaminones and DMSO. DMSO was activated by the acid and provided the one-carbon unit. An easy synthetic route to hetero-anthracene derivatives. Abstract: A metal-free p -toluenesulfonic acid (TsOH·H2 O) mediated synthesis of 3-ketoquinolines from anilines, enaminones and DMSO has been developed. In this transformation, DMSO was activated by TsOH·H2 O and provided the one-carbon unit of the 3-ketoquinolines. A plausible mechanism involving an electrophilic sulfenium ion intermediate was proposed.