A reaction of 2-carbonyl-substituted 1H-benzo[f]chromenes with N-arylamides of cyanoacetic acid

A reaction of 2-trifluoroacetyl-1 H -benzo[ f ]chromenes with N -arylamides of cyanoacetic acid led to the synthesis of a series of 2-oxo-6-trifluoromethylpyridine-3-carboxamides as products of a cascade of the carbo-Michael reaction, Thorpe–Ziegler cyclization, and Dimroth rearrangement. In the cas...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2024-04, Vol.60 (3-4), p.156-160
Main Authors: Osipov, Dmitry V., Krasnikov, Pavel E., Artemenko, Alina A.
Format: Article
Language:English
Subjects:
Adducts
Carbonyls
Chemistry
Chemistry and Materials Science
Michael reaction
Organic Chemistry
Pharmacy
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Summary:A reaction of 2-trifluoroacetyl-1 H -benzo[ f ]chromenes with N -arylamides of cyanoacetic acid led to the synthesis of a series of 2-oxo-6-trifluoromethylpyridine-3-carboxamides as products of a cascade of the carbo-Michael reaction, Thorpe–Ziegler cyclization, and Dimroth rearrangement. In the case of 1 H -benzo[ f ]chromene-2-carbaldehydes, the corresponding Knoevenagel adducts were isolated.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-024-03312-4