Formation of 3-[2-oxo-2-(2-heteryl)ethylidene]-3,4-dihydroquinoxalin-2(1H)-ones in the reaction of 5-aryl-4-heteroyl-3-hydroxy-1-thiazolyl-3-pyrrolin-2-ones with o-phenylenediamine
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We have previously shown that the reaction of 1,5-diaryl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones with o-phenylenediamine gives dihydropyrrolo[2,3-b]quinoxalines . A similar process accompanied by dehydrogenation takes place upon fusing 1,5-diaryl-3-hydroxy-4-methylsulfonyl-3-pyrrolin-2-ones with o-phenylenediamine . In the case of the reaction of 1,5-diaryl-4-tert-butoxycarbonyltetrahydropyrrole-2,3-diones with o-phenylenediamine the single reaction product is a 1,2-diaryl-3,10-dioxo-1,2,4,9-tetrahydro-pyrrolo[3,4-b][1,5]benzodiazepines .
With the aim of further examining the properties of the substituted pyrrole-2,3-diones, we have studied the reaction of 5-aryl-4-heteroyl-3-hydroxy-1-thiazolyl-3-pyrrolin-2-ones with o-phenylenediamine. The starting compounds were prepared according to the previously reported method .
Refluxing compounds 1, 2 with o-phenylenediamine in glacial acetic acid for 3 h gives only 3-[2-oxo-2-(2-heteryl)ethylidene]-3,4-dihydroquinoxalin-2(1H)...
Keywords5-aryl-4-heteroyl-3-hydroxy-1-thiazolyl-3-pyrrolin-2-ones binucleophiles o-phenylene-diamine quinoxalones
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