Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5222738 | Tetrahedron | 2009 | 4 Pages |
Abstract
2-Arylazo-1-vinylpyrroles 1-6 react with CF3CO2H (benzene, reflux, 5Â h) in a peculiar way: instead of expected electrophilic addition of CF3CO2H to the N-vinyl group, the latter is transferred to the azo group followed by NN bond cleavage to afford substituted 2-methylquinolines 10-12 in up to 56% yields. The reaction was shown (1H, 13C, and 15N NMR) to start with the protonation of the azo group with further inter- and intramolecular involving of two protonated N-vinyl groups to finally build up the quinoline cycle over the aryl moiety.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Elena Yu. Schmidt, Elena Yu. Senotrusova, Igor A. Ushakov, Al'bina I. Mikhaleva, Boris A. Trofimov,