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Electrophilic and nucleophilic substitution in oxazolo[3,2-f]xanthines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Bromination of 2-aryloxazolo[3,2-flxanthines gives the 3-bromoderivatives whereas 8-methyl-2-phenyloxazolo[3,2-f]xanthine is nitrated in the para-position of the phenyl substituent. Alkylation of oxazolo[3,2-f]xanthines by ethylmonoiodoacetate gives the ethyl esters of oxazolo[3,2-f]xanthinyl-6-acetic acids. Reaction of oxazolo[3,2-f]xanthines with sodium sulfide gives thiazolo[3,2-f]xanthines whereas the reaction with secondary amines opens the oxazole ring.

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Literature Cited

  1. N. I. Romanenko, N. A. Klyuev, I. V. Fedulova, B. A. Priimenko, S. N. Garmash, A. Yu. Chervinskii, and A. N. Stepanov, Khim. Geterotsikl. Soedin., No. 8, 1133 (1986).

    Google Scholar 

  2. S. N. Garmash, B. A. Priimenko, N. A. Klyuev, N. I. Romanenko, V. A. Golets, and T. A. Kozik, Khim. Geterotsikl. Soedin., No. 4, 534 (1988).

    Google Scholar 

  3. V. I. Minkin, B. Ya. Simkin, and R. M. Minyaev, Theory of Molecular Structure [in Russian], Vysshaya Shkola, Moscow (1979).

    Google Scholar 

  4. J. Klosa, J. Prakt. Chem., 6, 182 (1958).

    Google Scholar 

  5. A. N. Krasovskii, M. I. Yurchenko, P. M. Kochergin, and I. I. Soroka, Khim. Geterotsikl. Soedin., No. 8, 1121 (1975).

    Google Scholar 

  6. R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York (1974).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1396–1399, October, 1990.

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Garmash, S.N., Skul'skaya, E.A., Priimenko, B.A. et al. Electrophilic and nucleophilic substitution in oxazolo[3,2-f]xanthines. Chem Heterocycl Compd 26, 1164–1167 (1990). https://doi.org/10.1007/BF00472193

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  • DOI: https://doi.org/10.1007/BF00472193

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