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Synthesis and study of new 2-aryl-1-(4-nitrophenyl)-1,1a-dihydroazireno[1,2-a]quinoxaline derivatives

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New derivatives of photochromic 2-aryl-1-(4-nitrophenyl)-1,1a-dihydroazireno[1,2-a]quinoxalines were synthesized by condensation of 4-methyl-and 4,5-dimethyl-1,2-phenylenediamine with 1,3-diaryl-2,3-dibromopropan-1-ones. The reactions of 4-methyl-1,2-phenylenediamine produce mixtures of regioisomers. The chemical properties of the reaction products were studied. The structure of one of the latter was established by X-ray diffraction.

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  1. A. Padwa and S. S. Murphree, Prog. Heterocycl. Chem., 1999, 11, 66.

    Article  CAS  Google Scholar 

  2. V. D. Orlov, N. P. Vorob’eva, A. A. Tishchenko, and I. P. Krainov, Zh. Prikl. Spektrosk., 1991, 54, 638 [J. Appl. Spectr., 1991, 54, 403 (Engl. Transl.)].

    CAS  Google Scholar 

  3. H. W. Heine, R. H. Weese, and R. A. Cooper, J. Org. Chem., 1967, 32, 2708.

    Article  CAS  Google Scholar 

  4. H. W. Heine and R. P. Henzel, J. Org. Chem., 1969, 34, 171.

    Article  CAS  Google Scholar 

  5. V. D. Orlov, F. G. Yaremenko, N. N. Kolos, N. S. Pivnenko, and V. F. Lavrushin, Dokl. Akad. Nauk Ukr. SSR, Ser. B [Reports Ukr. Acad. Sci., Ser. B], 1978, No. 3, 247 (in Russian).

  6. K. I. Pashkevich and O. G. Khomutov, Zh. Org. Khim., 1999, 35, 106 [Russ. J. Org. Chem., 1999, 35, 100 (Engl. Transl.)].

    Google Scholar 

  7. A. I. Zbruyev, N. P. Vorob’eva, and F. G. Yaremenko, Tez. dokl. Ukrain. konf. “Khimiya azotsoderzhashchikh geterotsiklov” [Abstrs of Papers, Ukrainian Conf. “Chemistry of Nitrogen-Containing Heterocycles”], Kharkov, 1997, 24 (in Russian).

  8. V. D. Orlov, N. P. Vorob’eva, N. N. Demenkova, V. S. Chesnovskii, and F. G. Yaremenko, Khim. Geterotsikl. Soedin., 1988, 328 [Chem. Heterocycl. Compd., 1988, 24, 267 (Engl. Transl.)].

    Google Scholar 

  9. N. N. Kolos, V. D. Orlov, E. Ya. Yuzefovskaya, F. G. Yaremenko, N. P. Vorob’eva, O. V. Shishkin, Yu. T. Struchkov, and S. M. Ivkov, Khim. Geterotsikl. Soedin., 1995, 950 [Chem. Heterocycl. Compd., 1995, 31, 827 (Engl. Transl.)].

    Google Scholar 

  10. A. Gazit, H. App, G. McMahon, J. Chen, A. Levitzki, and F. D. Bohmer, J. Med. Chem., 1996, 39, 2170.

    Article  CAS  Google Scholar 

  11. A. A. H. Saeed and E. K. Ebraheem, J. Heterocycl. Chem., 1983, 20, 1739.

    Article  CAS  Google Scholar 

  12. V. D. Orlov, F. G. Yaremenko, N. N. Kolos, and V. F. Lavrushin, Khim. Geterotsikl. Soedin., 1980, 544 [Chem. Heterocycl. Compd., 1980, 16, 424 (Engl. Transl.)].

    Google Scholar 

  13. Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 1989, 58, 713 [Russ. Chem. Rev., 1989, 58 (Engl. Transl.)].

    CAS  Google Scholar 

  14. V. D. Orlov, F. G. Yaremenko, Yu. N. Surov, and V. F. Lavrushin, Zh. Obshch. Khim., 1979, 49, 2602 [J. Gen. Chem. USSR, 1979, 49, 2305 (Engl. Transl.)].

    CAS  Google Scholar 

  15. G. M. Sheldrick, SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data, Rev. 5.1, Siemens Analytical X-ray Instruments Inc. (Germany), 1998.

    Google Scholar 

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 350–356, February, 2006.

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Zbruyev, A.I., Yaremenko, F.G., Chebanov, V.A. et al. Synthesis and study of new 2-aryl-1-(4-nitrophenyl)-1,1a-dihydroazireno[1,2-a]quinoxaline derivatives. Russ Chem Bull 55, 362–368 (2006).

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