Article ; Online: Arylative Methylation of 2,3-Dihydropyrazines and Pyrazinones Using Dimethyl Sulfoxide as a C1 Source.
The Journal of organic chemistry
2023 Volume 88, Issue 5, Page(s) 2931–2941
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 ... ...
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. |
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Language | English |
Publishing date | 2023-02-14 |
Publishing country | United States |
Document type | Journal Article |
ZDB-ID | 123490-0 |
ISSN | 1520-6904 ; 0022-3263 |
ISSN (online) | 1520-6904 |
ISSN | 0022-3263 |
DOI | 10.1021/acs.joc.2c02675 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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