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Polycyclic rod-shaped azo dyes based on aminophenylpyrimidines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have synthesized rod-shaped tricyclic monoazo and bisazo dyes based on amino derivatives of arylpyrimidines and N,N-dialkylanilines orp-nitroso-N,N-dialkylanilines. We have shown that the process of azo coupling of the diazonium salt obtained from 2,5-bis(p-arninophenyl)pyritnidine is accompanied by dediazoniation, with substitution of the diazonium group by hydrogen or an aryl group. The monoazo dyes obtained display mesomorphic properties which are absent in the bisazo dyes.

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References

  1. A. V. Ivashchenko, Dichroic Dyes for Liquid Crystal Displays, CRC Press, Boca Raton (1994).

    Google Scholar 

  2. S. Wu, J. D. Margerum, M. Ho, and B. M. Fung, Appl, Phys. Lett.,64, 2191 (1994).

    Google Scholar 

  3. Dichroic Dyes for Liquid-Crystal Displays. Aniline Dye Industry Series [in Russian], Rev. Inf. MNPO NIOPiK; NIITÉKhIM, Moscow (1987).

  4. M. Kaneko, T. Ozawa, T. Yoneyama, S. Imazeki, A. Mucoh, and M. Sato, Eur. Pat. Appl. 76,633; Chem. Abstr.,99, 46062 (1983).

    Google Scholar 

  5. M. Kaneko, T. Yoneyama, J. Iwanami, S. Imazeki, A. Mukoo, and M. Sato, Eur. Pat. Appi. 98,522; Chem. Abstr.,100, 148633 (1984).

    Google Scholar 

  6. M. A. Mikhaleva, G. A. Igonina, V. T. Lazareva, V. G. Rumyantsev, and V. P. Mamaev, Khim. Geterotsiki. Soedin., No. 2, 209 (1993).

  7. L. Z. Gandel'sman, S. V. Shelyazhenko, L. A. Nechitailo, Yu. A. Fialkov, and T. S. Plyusnina, Ukr. Khim. Zh.,54, 608 (1988).

    Google Scholar 

  8. Houben-Weyl, Methods of Organic Chemistry [in German], Georg Thieme Verlag, Stuttgart/New York (1990); Vol. E 161/2, p. 1052.

    Google Scholar 

  9. D. F. De Tar and M. N. Turetzky, J. Am. Chem. Soc.,77, 1745 (1955).

    Google Scholar 

  10. C. Galli, Chem. Rev.,88, 765 (1988).

    Google Scholar 

  11. H. Gies and E. Pfeil, Lieb. Ann.,578, 11 (1952).

    Google Scholar 

  12. R. Nishiyama, Tetrahedron Lett., No. 15, 1403 (1967).

  13. J.H. Gorvin, J. Chem. Soc., No. 7, 1693 (1951).

  14. I. Takagishi, Y. Hashida, and K. Matsui, Bull. Chem. Soc. Jpn.,52, 2635 (1979).

    Google Scholar 

  15. G. Winter, H. Hartung, W. Brandt, and M. Jaskolski, Mol. Cryst. Liq. Cryst.,150b, 289 (1987).

    Google Scholar 

  16. S. Takenaka, T. Hirobata, and S. Kusabayashi, Bull. Chem. Soc. Jpn.,58, 1079 (1985).

    Google Scholar 

  17. V. P. Borovik, V. A. Semikolenov, and V. P. Mamaev, Izv. Sibirsk. Otdel. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 4, 94 (1988).

  18. V. P. Borovik, A. I. Shadrina, and V. P. Mamaev, Sibirsk. Khim. Zh., No. 6, 77 (1991).

  19. V. P. Borovik, S. G. Baram, E. Yu. Kozlova, and V. P. Mamaev, Izv. Sibirsk. Otdel. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 5, 97 (1985).

  20. R. M. Wagner and C. Jutz, Chem. Ber.,104, 2975 (1971).

    Google Scholar 

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Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences, Novosibirsk 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 693–702, May, 1996. Original article submitted January 25, 1996.

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Sedova, V.F., Borovik, V.P., Mikhaleva, M.A. et al. Polycyclic rod-shaped azo dyes based on aminophenylpyrimidines. Chem Heterocycl Compd 32, 596–604 (1996). https://doi.org/10.1007/BF01164793

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