Issue 123, 2015

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
19 okt 2015
Accepted
16 nov 2015
First published
18 nov 2015

RSC Adv., 2015,5, 101641-101646

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

P. S. Mahajan, S. D. Tanpure, N. A. More, J. M. Gajbhiye and S. B. Mhaske, RSC Adv., 2015, 5, 101641 DOI: 10.1039/C5RA21801B

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