Journal
TETRAHEDRON
Volume 124, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.132963
Keywords
Darzens condensation; Hinsberg-Ko?rner cyclo-annulation; 3-Benzylquinoxalin-2(1H)-ones; Aryloxirane-2-carboxamides; 5-Arylidene-2; 2-dimethyl-1; 3-oxazolidin-4-ones; 4-Formyl-3-benzyl-3; 4-dihydroquinoxalin-2(1H)-ones
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Funding
- Russian Science Foundation
- [18-13-00315-p]
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A facile and highly efficient strategy has been proposed for the synthesis of 3-benzylquinoxalin-2(1H)-ones and their partially reduced N-formyl derivatives, featuring mild conditions, easy work-up, practicality, and robustness.
A facile and highly efficient strategy has been delineated for the synthesis of 3-benzylquinoxalin-2(1H)-ones and their partially reduced N-formyl derivatives via a Hinsberg-Ko euro rner type cyclo-annulation re-action using 5-arylidene-2,2-dimethyl-1,3-oxazolidin-4-ones as pyruvate surrogates. 3-Benzylquinoxalin-2(1H)-ones with a wide range of substituents in both the benzyl moiety and the quinoxaline ring are formed in good to excellent yields and are easily converted into partially reduced N- formyl derivatives when boiled in a mixture of formic acid and formamide (1:1). The method features are mild condition, easy work-up (a simple filtration), practicality and robustness, excellent tolerance to the nature of substituents in starting compounds.(c) 2022 Published by Elsevier Ltd.
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