Acid-Catalyzed Heterocyclization of Trialkylnaphthazarin Thioglucosides in Angular Quinone-Carbohydrate Tetracycles


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Abstract

Tetracyclic naphthoquinone-carbohydrate conjugates with an angular-fused heterocycle were obtained for the first time by the intramolecular condensation of naphthazarin thioglucosides in a mixture of n-butanol and methanesulfonic acid under reflux. The competing reaction is hydrolysis of the thioglucosidic bond with formation of trialkylmercaptonaphthazarins.

About the authors

Y. E. Sabutskii

Elyakov Pacific Institute of Bioorganic Chemistry

Email: sergpol@piboc.dvo.ru
Russian Federation, pr. 100 let Vladivostoku 159, Vladivostok, 690022

V. A. Denisenko

Elyakov Pacific Institute of Bioorganic Chemistry

Email: sergpol@piboc.dvo.ru
Russian Federation, pr. 100 let Vladivostoku 159, Vladivostok, 690022

R. S. Popov

Elyakov Pacific Institute of Bioorganic Chemistry

Email: sergpol@piboc.dvo.ru
Russian Federation, pr. 100 let Vladivostoku 159, Vladivostok, 690022

S. G. Polonik

Elyakov Pacific Institute of Bioorganic Chemistry

Author for correspondence.
Email: sergpol@piboc.dvo.ru
Russian Federation, pr. 100 let Vladivostoku 159, Vladivostok, 690022

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