Abstract
Quinoxalin-2-one (1) reacts with ethyl acetoacetate in trifluoroacetic acid (TFA) to form 3-(2-oxopropylideno)-3,4-dihydroquinoxaline-2-one (2) and 3-(3-oxo-3,4- dihydroquinoxaline-2-(1H)-ylidene)methylquinoxaline-2-(1H)-one (3). The reaction product 3 was also obtained by heating the compound 1 with acetone in the presence of TFA.
Highlights
Compounds with various types of biological activity were found among quinoxaline derivatives. [1, 2] Quinoxidine and Dioxidine were used as antimicrobial agents [3].The features of the synthesis and biological activity of quinoxaline derivatives are described in the review [4]
● The replacement of hydrogen led to the formation of water, which activated the process of cleavage of the dicarbonyl group of 3-(2-oxopropylideno)-3,4-dihydroquinoxaline-2-one
● The formation of 3-(3-oxo-3,4-dihydroquinoxaline-2-(1H)-ylidene) methylquinoxaline-2-(1H)-one was the result of C,C-coupling of compounds quinoxaline-2-one and 3-(2-oxopropylideno)-3,4dihydroquinoxaline-2-one, to the reaction of quinoxaline-2-one 1 with acetone
Summary
● The replacement of hydrogen led to the formation of water, which activated the process of cleavage of the dicarbonyl group of 3-(2-oxopropylideno)-3,4-dihydroquinoxaline-2-one. The acyl group of com pound 3-(2-oxopropylideno)-3,4-dihydroquinoxaline-2-one was "vicarious" in this reaction. ● The formation of 3-(3-oxo-3,4-dihydroquinoxaline-2-(1H)-ylidene) methylquinoxaline-2-(1H)-one was the result of C,C-coupling of compounds quinoxaline-2-one and 3-(2-oxopropylideno)-3,4dihydroquinoxaline-2-one, to the reaction of quinoxaline-2-one 1 with acetone
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