TY - JOUR T1 - Ammonium persulfate activated DMSO as a one-carbon synthon for the synthesis of methylenebisamides and other applications JF - RSC Advances Y1 - 2015 A1 - Mahajan, Pankaj S. A1 - Tanpure, Subhash D. A1 - More, Namita A. A1 - Gajbhiye, Jayant M. A1 - Mhaske, Santosh B. AB -

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.

PB - ROYAL SOC CHEMISTRY CY - THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND VL - 5 IS - 123 U3 -

Foreign

U4 - 3.289 ER -