Acid-catalyzed rearrangement of 3-(β-2-aminostyryl)quinoxalin-2(1H)ones—a new and efficient method for the synthesis of 2-benzimidazol-2-ylquinolines

The reaction of 3‐ethoxycarbonylmethylene‐3,4‐dihydroquinoxalin‐2(1H)‐one 5 with the Vilsmeier reagent, the treatment of 3‐(3,4‐dihydroquinoxalin‐2(1H)‐on‐3‐yl)‐1,2‐dihydro‐1,5‐benzodiazepin‐2(1H)‐one hydrochloride 7 with 10% sodium hydroxide and 3‐benzimidazoylquinoxaline‐2(1H)‐one 3 with both 1,2‐phenylenediamine dihydrochloride, and the reactions of 1,2‐phenylenediamine have been reinvestigated, and the structures of these reaction products have been revised. The aforementioned reactions have been shown to proceed with the formation of 1‐N,N‐dimethylaminomethylene‐2‐oxo‐1,2‐dihydrofuro[2,3‐b]quinoxaline 10 in the first case, the formation of 3‐[2‐(benzimidazol‐2‐on‐1‐yl)vinyl]‐1H‐quinoxalin‐2‐one 12 in the second case, and the formation of 2,3‐bis‐(1H‐benzimidazol‐2‐yl)quinoxaline 17 in the third case and not the formation of 3‐(N,N‐dimethylaminocarbonyl)furo[2,3‐b]quinoxaline hydrochloride 6, the free base of 3‐(3,4‐dihydroquinoxalin‐2(1H)‐on‐3‐yl)‐1,2‐dihydro‐1,5‐benzodiazepin‐2(1H)‐one 7, that is, compound 11 and benzodiazepine derivative 4, as has been described earlier. In the third case, the formation of 2,3‐bis‐(1H‐benzimidazol‐2‐yl)quinoxaline 17 occurs according to the novel quinoxalin‐2(1H)‐one benzimidazole rearrangement discovered by us. The potential mechanisms for the investigated reactions are discussed.

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Rearrangements of Quinoxalin(on)es for the Synthesis of Benzimidazol(on)es

Мамедов

2016

Quinoxalines

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Acid-catalyzed rearrangement of 3-(β-2-aminostyryl)quinoxalin-2(1H)ones—a new and efficient method for the synthesis of 2-benzimidazol-2-ylquinolines

Cited by 24 publications

References 45 publications

ChemInform Abstract: Acid‐Catalyzed Rearrangement of 3‐(β‐2‐Aminostyryl)quinoxalin‐2(1H)ones — A New and Efficient Method for the Synthesis of 2‐Benzimidazol‐2‐ylquinolines.

ChemInform Abstract: Acid‐Catalyzed Rearrangement of 3‐(β‐2‐Aminostyryl)quinoxalin‐2(1H)ones — A New and Efficient Method for the Synthesis of 2‐Benzimidazol‐2‐ylquinolines.

Three Questionable Cases in the Chemistry of Quinoxalines and Benzodiazepines in the Way of the Syntheses of Benzimidazoles

Rearrangements of Quinoxalin(on)es for the Synthesis of Benzimidazol(on)es

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