1. Intramolecular cyclization of 9,10-anthraquinones promoted by reaction with halogenophosphoranes
- Author
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Rashid Z. Musin, A. V. Ilyasov, Igor A. Litvinov, A. A. Kutyrev, K. M. Enikeyev, V. A. Naumov, V. V. Biryukov, O. N. Katayeva, and V. V. Moskva
- Subjects
chemistry.chemical_classification ,Intramolecular reaction ,Stereochemistry ,Organic Chemistry ,Intramolecular cyclization ,Biochemistry ,Carbonyl group ,Haloketone ,Medicinal chemistry ,Anthraquinone ,Quinone ,chemistry.chemical_compound ,chemistry ,Drug Discovery ,Anthraquinones ,Phenols - Abstract
The results of the research of an unknown reaction of halogenophosphoranes (Ia-Ie) with peri-oxy(amino)-9,10-anthraquinones leading to the formation of anthrones (Via-Ie, XIII) and tetrahydroanthracenes (XIa,b) are reported. The scheme of reaction includes the formation of phosphabenzanthrone (V) and anthraquinone (III) which was fixed by a low temperature 31p NMR spectroscopy. The driving force of discovered reaction of anthraquinone cyclization is explained by specific character of transference of electronic influence from substituents to a carbonyl group contained in anthraquinones. Certain properties of products formed having an unusual structure from the viewpoint of the chemistry of anthraquinones are described.
- Published
- 1990
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