Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications

TitleAmmonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications
Publication TypeJournal Article
Year of Publication2015
AuthorsMahajan, PS, Tanpure, SD, More, NA, Gajbhiye, JM, Mhaske, SB
JournalRSC Advances
Volume5
Issue123
Pagination101641-101646
Date PublishedNOV
ISSN2046-2069
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 beta-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.

DOI10.1039/c5ra21801b
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.289

Divison category: 
Organic Chemistry