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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 3, pp 327–335 | Cite as

Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives

  • L. M. PotikhaEmail author
  • V. A. Kovtunenko
  • A. V. Turov
  • G. V. Palamarchuk
  • R. I. Zubatyuk
  • O. V. Shishkin
Article

The direction of the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one (γ-bromodypnone) with hydrazines depends on the nature of the substituent they contain. Reaction with 1-methylhydrazinium hydrosulfate gives 1-methyl-3,5-diphenylpyridazin-1-ium bromide but carboxylic acid hydrazides give N-(2,4-diphenyl-1H-pyrrol-1-yl)carboxylic acid amides. γ-Bromodypnone and phenylhydrazine give both 1,3,5-triphenyl-1,4-dihydropyridazine and N,2,4-triphenyl-1H-pyrrol-1-amine (15%). 1-(2,4-Dinitrophenyl)hydrazine gives the 2,4-dinitrophenylhydrazone of (Z)-4-bromo-1,3-diphenyl-2-buten-1-one. Condensation of 2,4-diphenyl-1H-pyrrol-1-amine with aromatic aldehydes readily leads to N-(arylmethylidene)-2,4-diphenyl-1H-pyrrol-1-amines and alkylation with methyl iodide gives N,N-dimethyl-2,4-diphenyl-1H-pyrrol-1-amine.

Keywords

1-aminopyrrole γ-bromodypnone 2,4-diphenyl-1H-pyrrol-1-amine 3,5-diphenylpyri-dazine 

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References

  1. 1.
    V. A. Kovtunenko, Medicinal Compounds with Activity on the CNS System [in Russian], VTF Perun, Kiev (1997).Google Scholar
  2. 2.
    S. E. Korostova, A. I. Mikhaleva, A. M. Vasil'tsov, and B. A. Trofimov, Zh. Org. Khim., 34, 967 (1998).Google Scholar
  3. 3.
    R. C. Effland and J. T. Klein, US Pat. 4546105; Chem. Abstr., 104, 186307 (1986).Google Scholar
  4. 4.
    J. Kulagowski, J. Janusz, and P. D. Leeson, US Pat. 2265372; Chem. Abstr., 120, 134504 (1993).Google Scholar
  5. 5.
    W. Flitsch, U. Lewinski, R. Temme, and B. Wibbeling, Liebigs Ann. Chem., 623 (1990).Google Scholar
  6. 6.
    M. McLeod, N. Boudreault, and Y. Leblanc, J. Org. Chem., 61, 1180 (1996).CrossRefGoogle Scholar
  7. 7.
    R. A. Gadzhaly, V. M. Fedoseev, N. A. Netkacheva, Ch. N. Akhmedov, and M. Sh. Sultanova. Khim. Geterotsikl. Soedin., 998 (1989). [Chem. Heterocycl. Comp., 25, 837 (1989)].Google Scholar
  8. 8.
    A. N. Kost, I. I. Grandberg, A. P. Terent'ev, and S. I. Milovanova, Zh. Obshch. Khim., 29, 93 (1959).Google Scholar
  9. 9.
    L. M. Potikha and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 626 (2007). [Chem. Heterocycl. Comp., 43, 523 (2007)].Google Scholar
  10. 10.
    R. Faragher and T. L. Gilchrist, J. Chem. Soc., Perkin Trans. 1, 336 (1976).Google Scholar
  11. 11.
    L. M. Potikha and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 848 (2006). [Chem. Heterocycl. Comp., 42, 741 (2006)].Google Scholar
  12. 12.
    Y. Tamura and N. Tsujimoto, Tetrahedron, 28, 21 (1972).CrossRefGoogle Scholar
  13. 13.
    M. Fischer, Liebigs Ann. Chem., 527, 1 (1932).Google Scholar
  14. 14.
    Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 58, 713 (1989).Google Scholar
  15. 15.
    H.-B. Burgi and J. D. Dunitz, Structure Correlation, Vol. 2, VCH, Weinheim (1994), p. 741.CrossRefGoogle Scholar
  16. 16.
    J. I. Cook, C. A. Hunter, C. M. R. Low, A. Perez-Velasco, and J. G. Vinter, Angew. Chem., Int. Ed., 46, 3706 (2007).CrossRefGoogle Scholar
  17. 17.
    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 (1998).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • L. M. Potikha
    • 1
    Email author
  • V. A. Kovtunenko
    • 1
  • A. V. Turov
    • 1
  • G. V. Palamarchuk
    • 2
  • R. I. Zubatyuk
    • 2
  • O. V. Shishkin
    • 2
  1. 1.Taras Shevchenko National UniversityKievUkraine
  2. 2.Institute for Single CrystalsUkraine National Academy of SciencesKharkivUkraine

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