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New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives

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Abstract

The reactions of benzene-1,2-diamine with 5-substituted 2-(alkylsulfanyl)-4-methylpyrimidin-6(1H)-ones and 2-(propylsulfanyl)- and 5-iodo-2-(propylsulfanyl)-3,4-dihydroquinazolines at 175–185°C under solvent-free conditions unexpectedly afforded benzo[4,5]imidazo[1,2-a]pyrimidine, benzo[4,5]imidazo[2,1-b]-quinazoline, and 2,2′-(benzene-1,2-diyldiimino)bis[pyrimidin-4(3H)-ones]. The described reaction is the first example of synthesis of these heterocyclic systems by fusion of benzimidazole to pyrimidine or quinazoline and is likely to follow ANRORC mechanism.

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References

  1. Shaabani, A., Farhangi, E., and Shaabani, S., Iran. J. Chem. Chem. Eng., 2013, vol. 32, p. 3.

    CAS  Google Scholar 

  2. Shaabani, A., Seyyedhamzeh, M., Ganji, N., and Ng, S.W., J. Iran. Chem. Soc., 2014, vol. 11, p. 481.

    Article  CAS  Google Scholar 

  3. Nowicka, A., Liszkiewicz, H., Nawrocka, W.P., Wietrzyk, J., Kempinska, K., and Drys, A., Cent. Eur. J. Chem., 2014, vol. 12, p. 1047.

    Article  CAS  Google Scholar 

  4. Tardy, S., Orsato, A., Mologni, L., Bisson, W.H., Donadoni, C., Gambacorti-Passerini, C., Scapozza, L., Gueyrard, D., and Goekjian, P.G., Bioorg. Med. Chem., 2014, vol. 22, p. 1303.

    Article  CAS  Google Scholar 

  5. Sirko, S.M., Gorobets, N.Yu., Musatov, V.I., and Desenko, S.M., Molecules, 2009, vol. 14, p. 5223.

    Article  CAS  Google Scholar 

  6. Carpenter, R.D., Lam, K.S., and Kurth, M.J., J. Org. Chem., 2007, vol. 72, p. 284.

    Article  CAS  Google Scholar 

  7. Murav’eva, K.M., Arkhangel’skaya, T.V., Shchukina, M.N., Zykova, T.N., and Pershin, G.N., Khimiya Geterotsiklicheskikh Soedinenii (Chemistry of Heterocyclic Compounds), Giller, S.A., Ed., Riga: Zinatne, 1967, vol. 1, p. 411; Chem. Abstr., 1969, vol. 70, no. 96 748 u.

  8. Makisumi, Y., Chem. Pharm. Bull., 1964, vol. 12, p. 789.

    Article  CAS  Google Scholar 

  9. Chi, Y.F. and Kao, Y.S., J. Am. Chem. Soc., 1936, vol. 58, p. 769.

    Article  CAS  Google Scholar 

  10. Wheeler, H.L. and McFarland, D.F., Am. Chem. J., 1909, vol. 42, p. 101.

    CAS  Google Scholar 

  11. De Cat, A. and Van Dormael, A., Bull. Soc. Chim. Belg., 1950, vol. 59, p. 573.

    Article  Google Scholar 

  12. Dave, G.R., Mewada, G.S., and Amin, G.C., Acta Chim. Acad. Sci. Hung., 1962, vol. 34, p. 101.

    CAS  Google Scholar 

  13. Srivastava, K.S.L., Indian J. Appl. Chem., 1971, vol. 34, nos. 3–4, p. 145.

    CAS  Google Scholar 

  14. Bird, C.W., Tetrahedron, 1965, vol. 21, p. 2179.

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    A. A. Harutyunyan

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  1. A. A. Harutyunyan
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Correspondence to A. A. Harutyunyan.

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Original Russian Text © A.A. Harutyunyan, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 7, pp. 1018–1023.

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Harutyunyan, A.A. New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives. Russ J Org Chem 52, 1012–1017 (2016). https://doi.org/10.1134/S1070428016070150

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  • DOI: https://doi.org/10.1134/S1070428016070150

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