Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications. Issue 123 (25th November 2015)

• Record Type: Journal Article
• Authors: Mahajan, Pankaj S.; Tanpure, Subhash D.; More, Namita A.; Gajbhiye, Jayant M.; Mhaske, Santosh B.
• Is Part Of: RSC advances. Volume 5:Issue 123(2015)
• Page Start: 101641
• Page End: 101646
• Publication Date: 2015-11-25
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5ra21801b
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general and efficient access to symmetrical methylenebisamides from primary amides. Abstract : Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general and efficient access to symmetrical methylenebisamides from primary amides. This methodology was used to achieve a three-component Mannich reaction using acetophenone, saccharin and DMSO to furnish a β-amino ketone. It also provided a metal-free synthesis of thiadiazole and bis(phenyl)methane. Effectively, this method uses DMSO as a safer surrogate to formaldehyde. A mechanism for methylenebisamide formation involving radical intermediates has been proposed based on mechanistic studies.