A new heteropentacyclic system via coupling sterically crowded o-benzoquinone with o-phenylenediamines.

The reaction between 3,5-di(tert-butyl)-o-benzoquinone 1 and o-phenylenediamine performed under oxidative conditions that is highly sensitive to the reaction conditions (type of solvent, ratio of reactants, and duration of the reaction) gives rise to various derivatives of a new condensed 10H-quinoxalino[3,2,1-kl]phenoxazin-10-one heteropentacyclic system. The reaction of 1 with N-phenyl-o-phenylenediamine results in the formation of three phenazine-like compounds and, unexpectedly, a derivative of a new spiro[1,3]dioxole-2,2'-furanyl-1H-benzo[d]imidazole system. The molecular structures of the prepared compounds were authenticated by NMR, mass spectra and X-ray crystallography data.

Citation

Eugeny Ivakhnenko, Vasily Malay, Oleg Demidov, Pavel Knyazev, Nadezhda Makarova, Vladimir Minkin. A new heteropentacyclic system via coupling sterically crowded o-benzoquinone with o-phenylenediamines. Organic & biomolecular chemistry. 2023 Jan 18;21(3):621-631

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PMID: 36562504

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