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Condensation of 5-amino-4-arylpyrazoles with itaconic acid and maleic anhydride

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Chemistry of Heterocyclic Compounds Aims and scope

Substituted 5-amino-4-arylpyrazoles on condensation with itaconic acid form substituted tetrahydropyrazolo[1,5-a]pyrimidines, and on condensation with maleic anhydride form 2,3-dihydro-1H-imidazolo[1,2-b]pyrazoles, which on more extended heating rearrange into tetrahydro-pyrazolo[1,5-a]pyrimidines.

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References

  1. S. Selleri, F. Bruni, C. Costagli, A. Costanzo, G. Guerrini, G. Ciciani, P. Gratteri, C. Bonaccini, P. Malmberg Aiello, F. Besnard, S. Renard, B. Costa, and C. Martini, J. Med. Chem., 46, 310 (2003).

    Article  CAS  Google Scholar 

  2. L. K. Gavrin, A. Lee, B. A. Provencher, W. W. Massefski, S. D. Huhn, G. M. Ciszewski, D. C. Cole, and J. C. McKew, J. Org. Chem., 72, 1043 (2007).

    Article  CAS  Google Scholar 

  3. F. J. Moy, A. Lee, L. K. Gavrin, Z. B. Xu, A. Sievers, E. Kieras, W. Stochaj, L. Mosyak, J. McKew, and D. H. H. Tsao, J. Med. Chem., 53, 1238 (2010).

    Article  CAS  Google Scholar 

  4. E. E. Emelina, A. A. Petrov, and A. V. Firsov, Zh. Org. Khim., 39, 299 (2003).

    Google Scholar 

  5. N. L. Nam, I. I. Grandberg, and V. I. Sorokin, Khim. Geterotsikl. Soedin., 1555 (2002). [Chem. Heterocycl. Compd., 38, 1371 (2002).]

    Google Scholar 

  6. V. D. Orlov, Kh. Kiroga, N. N. Kolos, and S. M. Desenko, Khim. Geterotsikl. Soedin., 962 (1988). [Chem. Heterocycl. Compd., 24, 791 (1988).]

  7. A. Costanzo, F. Bruni, G. Auzzi, S. Selleri, and L. Pecori Vettori, J. Heterocycl. Chem., 27, 695 (1990).

    Article  CAS  Google Scholar 

  8. R. V. Rudenko, S. A. Komykhov, S. M. Desenko, V. I. Musatov, O. V. Shishkin, I. A. Konovalova, E. V. Vashchenko, and V. A. Chebanov, Synthesis, 783 (2011).

  9. A. A. El-Agamey, S. O. Abdalla, and M. R. H. El-Moghayar, Monatsh. Chem., 115, 1413 (1984).

    Article  CAS  Google Scholar 

  10. M. H. Elnagdi, D. H. Fleita, and M. R. H. El-Moghayar, Tetrahedron, 31, 63 (1975).

    Article  CAS  Google Scholar 

  11. V. I. Minkin, A. D. Garnovskii, J. Elguero, A. R. Katritzky, and O. V. Denisko, Adv. Heterocycl. Chem., 76, 157 (2000).

    Article  CAS  Google Scholar 

  12. S. I. Filimonov, V. B. Lyskov, L. P. Vatlina, S. A. Filimonova, S. I. Firgang, G. A. Stashina, and A. S. Shashkov, Izv. Vuzov. Khim. Khim. Tekhnol., 51, No. 8, 15 (2008).

    CAS  Google Scholar 

  13. V. D. Orlov, M. Tuèni, N. N. Kolos, N. V. Getmanskii, and Kh. Kiroga, Khim. Geterotsikl. Soedin., 787 (1988). [Chem. Heterocycl. Compd., 24, 643 (1988).]

    Google Scholar 

  14. I. I. Grandberg, V.-P. Din, and A. N. Kost, Zh. Obshch. Khim., 31, 2311 (1961).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Yaroslavl State Technical University, 88 Moskovskii Ave., Yaroslavl, 150023, Russia

    S. I. Filimonov, M. K. Korsakov, Zh. V. Chirkova & I. G. Abramov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    G. A. Stashina & S. I. Firgang

  3. Voronezh State University, 1 Universitetskaya Sq., Voronezh, 394006, Russia

    Yu. A. Kovygin & Kh. S. Shikhaliev

Authors
  1. S. I. Filimonov
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  2. M. K. Korsakov
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  3. Zh. V. Chirkova
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  4. I. G. Abramov
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  5. G. A. Stashina
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  6. S. I. Firgang
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  7. Yu. A. Kovygin
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  8. Kh. S. Shikhaliev
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Corresponding author

Correspondence to S. I. Filimonov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1065-1072, July, 2013.

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Filimonov, S.I., Korsakov, M.K., Chirkova, Z.V. et al. Condensation of 5-amino-4-arylpyrazoles with itaconic acid and maleic anhydride. Chem Heterocycl Comp 49, 993–999 (2013). https://doi.org/10.1007/s10593-013-1337-7

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  • DOI: https://doi.org/10.1007/s10593-013-1337-7

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