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Pyrimidines

III. Dehydrogenation of 4-phenylbenzo[h]quinazoline derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Dehydrogenation of 2-hydroxy-4-phenyl-3, 4, 5, 6-tetrahydrobenzo[h]quinazoline with Pd/C, diphenyl disulfide, chloranil, and N-bromosuccinimide, was investigated. Dihydroderivatives of 2-hydroxy-4-phenylbenzo[h]quinazoline were obtained. The action of N bromosuccinimide led to dehydrogenation and bromination. Treatment of 2-hydroxy-4-phenylbenzo[h]quinazoline and its bromine derivative with phosphorus oxychloride, followed by hydrogenation, gave 4-phenylbenzo[h]quinazoline. The structures of the compounds prepared are confirmed by spectroscopic data.

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References

  1. V. P. Mamaev and V. F. Sedova, ZhOKh, Collection: Biologically Active Compounds (in press).

  2. D. J. Brown, E. Hoerger, and S. F. Mason, J. Chem. Soc., 211, 1955.

  3. I. E. Gearien and S. B. Binkley, J. Org. Chem., 23, 491, 1958.

    Google Scholar 

  4. N. W. Gabel and S. B. Binkley, J. Org. Chem., 23, 643, 1958.

    Google Scholar 

  5. G. H. Hitchings, P. B. Russell, and N. Whittaker, J. Chem. Soc., 1019, 1956.

  6. B. Lythgoe and L. S. Rayner, J. Chem. Soc., 2323, 1951.

  7. B. J. Brown and R. F. Evans, J Chem. Soc., 532, 1962.

  8. S. Gabriel, Ber., 36, 800, 1903.

    Google Scholar 

  9. R. Wilkendorf, Ber., 52, 606, 1919.

    Google Scholar 

  10. K. Schofield, J. Chem. Soc., 1937, 1952.

  11. Houben-Weyl, Methoden der Organischen Chemie, Stuttgart, 4/2, S. 192, 1955.

    Google Scholar 

  12. R. A. Barnes, J. Am. Chem. Soc., 70, 145, 1948.

    Google Scholar 

  13. R. Filler, Chem. Rev., 63, 21, 1963.

    Google Scholar 

  14. T. Nishiwaki, Chem. and Pharmac. Bull., 10, 1029, 1962;

    Google Scholar 

  15. I. Carbon, J. Org. Chem., 25, 1731, 1960.

    Google Scholar 

  16. Nakasaki, Nippon Kagaku Zasshi, 74, 403, 1953

    Google Scholar 

  17. N. N. Vorozhtsov, Jr. and V. A. Koptyug, ZhOKh, 28, 1646, 1958.

    Google Scholar 

  18. L. J. Bellamy, The Infra-Red Spectra of Complex Molecules [Russian translation], IL, Moscow, pp. 116, 194, 1963.

    Google Scholar 

  19. Yu. N. Sheinker and Yu. I. Pomerantsev, ZhOKh, 30, 79, 1956.

    Google Scholar 

  20. D. J. Brown, The Pyrimidines, J. Wiley and Sons, New York-London, p. 485, 1962.

    Google Scholar 

  21. Heterocyclic Compounds, edited by R. C. Elderfield [Russian translation], IL, Moscow, 6, p. 286, 1960.

    Google Scholar 

  22. A. E. Gillam and E. S. Stern, An Introduction to Electronic Absorption Spectroscopy in Organic Chemistry [Russian translation], IL, Moscow, p. 74, 1957.

    Google Scholar 

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For Part II see [1].

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Mamaev, V.P., Sedova, V.F. Pyrimidines. Chem Heterocycl Compd 1, 409–414 (1966). https://doi.org/10.1007/BF00473822

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  • DOI: https://doi.org/10.1007/BF00473822

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