A convenient microwave-assisted desulfitative dimethylamination of the 2(1H)-pyrazinone scaffold using N,N-dimethylformamide

Sharma, Anuj; Mehta Pravinchandra, Vaibhav; Van der Eycken, Erik

doi:10.1016/j.tet.2008.01.030

A convenient microwave-assisted desulfitative dimethylamination of the 2(1H)-pyrazinone scaffold using N,N-dimethylformamide

Author:

Sharma, Anuj

Mehta Pravinchandra, Vaibhav ; Van der Eycken, Erik

Keywords:

microwave-assisted organic synthesis (maos), 2(1h)-pyrazinone, dimethylamination, desulfitative, dmf, solution-phase synthesis, arylboronic acids, dimethylformamide, heterocycles, irradiation, derivatives, transition, inhibitors, taxoids, halides, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, microwave-assisted organic synthesis (MAOS), 2(1H)-pyrazinone, DMF, SOLUTION-PHASE SYNTHESIS, ARYLBORONIC ACIDS, IRRADIATION, DERIVATIVES, DECORATION, TAXOIDS, HALIDES, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3101 Biochemistry and cell biology, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

A convenient microwave-assisted methodology is developed for the generation of 5-chloro-3-(dimethylamino)pyrazin-2(1H)-ones. The method entails a chemoselective desulfitative removal of a phenylthioether bond upon DMF/H2O treatment in the presence of sodium carbonate, yielding the desired compounds in 73-96%. (c) 2008 Elsevier Ltd. All rights reserved.