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Synthesis of heterocycles on the basis of products of arylation of unsaturated compounds 22.* 3-Aryl-2-chloropropanal in the synthesis of N-Aryl-5-(R-benzyl)-1,3-thiazole-2-amines

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Chemistry of Heterocyclic Compounds Aims and scope

3-Aryl-2-chloropropanal was obtained by the reaction of arenediazonium chlorides with acrolein in the presence of copper(II) chloride. N-Aryl(2-pyridyl)-5-(R-benzyl)-1,3-thiazole-2-amines were formed in high yield by the reaction of these aldehydes with aryl- and 2-pyridylthioureas. The same compounds were obtained by the reaction of 5-(R-benzyl)-1,3-thiazole-2-amines with aniline.

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References

  1. M. D. Obushak, V. S. Matiychuk, and V. V. Turytsa, Tetrahedron Lett., 50, 6112 (2009).

    Article  CAS  Google Scholar 

  2. S. Ueda, H. Terauchi, M. Kawasaki, A. Yano, and M. Ido, Chem. Pharm. Bull., 52, 634 (2004).

    Article  CAS  Google Scholar 

  3. D. Zuev, J. A. Michne, S. S. Pin, J. Zhang, M. T. Taber, and G. M. Dubowchik, Bioorg. Med. Chem. Lett., 15, 431 (2005).

    Article  CAS  Google Scholar 

  4. A. Dondoni and A. Marra, Chem. Rev., 104, 2557 (2004).

    Article  CAS  Google Scholar 

  5. R. M. Borzilleri, R. S. Bhide, J. C. Barrish, C. J. D'Arienzo, G. M. Derbin, J. Fargnoli, J. T. Hunt, R. Jeyaseelan, A. Kamath, D. W. Kukral, P. Marathe, S. Mortillo, L. Qian, J. S. Tokarski, B. S. Wautlet, X. Zheng, and L. J. Lombardo, J. Med. Chem., 49, 3766 (2006).

    Article  CAS  Google Scholar 

  6. Y. Sagara, M. Mitsuya, M. Uchiyama, Y. Ogino, T. Kimura, N. Ohtake, and T. Mase, Chem. Pharm. Bull., 53, 437 (2005).

    Article  CAS  Google Scholar 

  7. S. Wang, C. Meades, G. Wood, A. Osnowski, S. Anderson, R. Yuill, M. Thomas, M. Mezna, W. Jackson, C. Midgley, G. Griffiths, J. Fleming, S. Green, I. McNae, S.-Y. Wu, C. McInnes, D. Zheleva, M. D. Walkinshaw, and P. M. Fischer, J. Med. Chem., 47, 1662 (2004).

    Article  CAS  Google Scholar 

  8. B. S. Zimenkovskii, R. V. Kutsyk, R. B. Lesyk, V. S. Matiychuk, N. D. Obushak, and T. I. Klofinskaya, Khim.-Farm. Zh., 40, No.6, 57 (2006).

    Google Scholar 

  9. J. V. Metzger (editor), Thiazole and Its Derivatives. John Wiley and Sons, London (1979), Vol. 3, p.23.

  10. A. R. Katritzky, C. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, Elsevier (1997), Vol. 6, p. 326.

  11. I. K. Moiseev, M. N. Zemtsova, and N. V. Makarova, Khim. Geterotsikl, Soed., 867 (1994). [Chem. Heterocycl. Comp., 30, 745 (1994)].

    Google Scholar 

  12. J. V. Metzger (editor), Thiazole and Its Derivatives. John Wiley and Sons, London (1979), Vol. 1, p. 165.

  13. J. M. Sprague and A. H. Land, in: R. Elderfield (editor), Heterocyclic Compounds (Russian translation). Izd-vo inostr. lit., Moscow (1961), Vol. 5, p.395.

  14. N. D. Obushak, V. S. Matiichuk, and N. I. Ganushchak, Zh. Org. Khim., 33, 1081 (1997).

    Google Scholar 

  15. N. D. Obushak, V. S. Matiichuk, R. Ya. Vasyl'shin, and Yu. V. Ostashok, Zh. Org. Khim., 40, 412 (2004).

    Google Scholar 

  16. D. S. Emolat'ev, V. L. Alifanov, V. B. Rybakov, E. V. Babaev, and E. V. Van der Eycken, Synthesis, 2083 (2008).

  17. A. P. Engoyan, K. A. Eliazyan, V. A. Pivazyan, E. A. Kazaryan, and V. V. Dovlatyan, Khim. Geterotsikl. Soedin., 1240 (2005). [Chem. Heterocycl. Comp., 41, 1062 (2005)].

    Google Scholar 

  18. M. Annese, A. B. Corradi, L. Forlani, C. Rizzoli, and P. Sgarabotto, J. Chem. Soc., Perkin Trans 2, 615 (1994).

  19. T. N. Birkinshaw, S. A. Harkin, P. T. Kaye, G. D. Meakins, and A. K. Smith, J. Chem. Soc., Perkin Trans 1, 939 (1982).

  20. G. C. Barrett, Tetrahedron, 36, 2023 (1980).

    Article  CAS  Google Scholar 

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Correspondence to N. D.Obushak.

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For Communication 21, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.4, 624-629, April 2010.

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Matiychuk, V.S., D.Obushak, N., Pidlypnyi, N.I. et al. Synthesis of heterocycles on the basis of products of arylation of unsaturated compounds 22.* 3-Aryl-2-chloropropanal in the synthesis of N-Aryl-5-(R-benzyl)-1,3-thiazole-2-amines. Chem Heterocycl Comp 46, 495–499 (2010). https://doi.org/10.1007/s10593-010-0537-7

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  • DOI: https://doi.org/10.1007/s10593-010-0537-7

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