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The Journal of Organic Chemistry

The Journal of Organic Chemistry

IF: 3.3
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Arylative Methylation of 2,3-Dihydropyrazines and Pyrazinones Using Dimethyl Sulfoxide as a C1 Source

Published:14 February 2023 DOI: 10.1021/acs.joc.2c02675 PMID: 36786556
Kuntal Palit, Nayim Sepay and Niranjan Panda*, 

Abstract

Divergent synthesis of α-C–H methylated pyrazines and pyrazinones using dimethyl sulfoxide as a nonconventional methylating agent under metal-free conditions was reported. Dimethyl sulfoxide-coordinated bromine cation pools generated from the treatment of dimethyl sulfoxide and 1,2-dibromoethane undergo Pummerer-type fragmentation to afford an electrophilic methyl(methylene)sulfonium ion for reaction with a carbon nucleophile followed by aromatization to afford α-methylated pyrazines and pyrazinones.

Substances (2)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Dimethyl sulfoxide 67-68-5 C2H6OS 1925 suppliers $5.00-$120900.00
1,2-Dibromoethane 106-93-4 C2H4Br2 476 suppliers $15.00-$1166.55

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