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Fused polycyclic nitrogen-containing heterocycles 20. Thiazolo[3,4-a]quinoxalines from 4-hydroxy-2-phenyliminothiazolidines and C-substituted 1,2-phenylenediamines

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Abstract

The condensation of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidine with 4,5-dimethyl-1,2-phenylenediamine affords 7,8-dimethyl-3-phenyl-1-phenyliminothiazolo[3,4-a]quinox-alin-4(5 H)- one; the condensation with 1,2-phenylenediamines containing different substituents at positions 4 and 5 gives both theoretically possible isomeric thiazolo[3,4-a]quinoxalines, which differ in the distribution of these substituents between positions 7 and 8 in the benzene ring of the quinoxaline system. 3a-Hydroxy-7,8-dimethyl-3-phenyl-l-phenylimino-3,3a-di-hydrothiazolo[3,4-a]quinoxalin4(5 H)- one was isolated and characterized as the intermediate of the reaction giving rise to thiazolo[3,4-a]quinoxaline from 4,5-dimethyl-1,2-phenylene-diamine. This intermediate is a covalent hydrate of the final product.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. A. Mamedov, N. A. Zhukova, T. N. Beschastnova, A. T. Gubaidullin, Ya. A. Levin & I. A. Litvinov

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  1. V. A. Mamedov
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  2. N. A. Zhukova
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  3. T. N. Beschastnova
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  4. A. T. Gubaidullin
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  5. Ya. A. Levin
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  6. I. A. Litvinov
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Correspondence to V. A. Mamedov.

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Dedicated to Academician A. I. Konovalov on his 75th birthday.

For Part 19, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 1904-200, January, 2009.

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Mamedov, V.A., Zhukova, N.A., Beschastnova, T.N. et al. Fused polycyclic nitrogen-containing heterocycles 20. Thiazolo[3,4-a]quinoxalines from 4-hydroxy-2-phenyliminothiazolidines and C-substituted 1,2-phenylenediamines. Russ Chem Bull 58, 191–202 (2009). https://doi.org/10.1007/s11172-009-0029-z

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  • DOI: https://doi.org/10.1007/s11172-009-0029-z

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