Skip to main content
SpringerLink
Log in

Dearylation with aromatization on cyclocondensation of 4-(dimethyl-amino)benzaldehyde, 2-phenacylaza-heterocycles, and 1,3-[N,C]dinucleophiles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Three-component cyclocondensation involving p-(dimethylamino)benzaldehyde, 2-phenacylazahetero-cycle, and a 1,3-[N,C]-nucleophile (3,5-dimethoxyaniline, 6-amino-1,3-dimethylpyrimidine-2,4-dione, 1-amino-3-methyl-5-phenylpyrazole) in boiling acetic acid is accompanied by aromatization of the initially formed annelated 4-(p-dimethylaminophenyl)-3-hetaryl-2-phenyl-1,4-dihydropyridines, the direction of which, with splitting off the dimethylaminophenyl substituent or its retention, is determined by the basicity of the hetaryl residue and the structure of the second ring, constructed on the binucleophile. A possible reaction mechanism is discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. C. Simon, T. Constantieux, and J. Rodriguez, Eur. J. Org. Chem., 4957 (2004).

  2. F. E. Sausinsh and G. Ya. Duburs, Khim. Geterotsikl. Soedin., 435 (1992). [Chem. Heterocycl. Comp., 28, 363 (1992)].

    Google Scholar 

  3. J. Quiroga, B. Insuastu, A. Hormaza, C. Saitz, and C. Julian, J. Heterocycl. Chem., 35, 575 (1998).

    Article  CAS  Google Scholar 

  4. A. Agarwal and P. M. S. Chauhan, Synth. Commun., 34, 4447 (2004).

    Article  CAS  Google Scholar 

  5. B. Loev and K. M. Snader, J. Org. Chem., 30, 1914 (1965).

    Article  CAS  Google Scholar 

  6. A. Singer and S. M. McElvain, Org. Synth. Coll., 2, 214 (1943).

    Google Scholar 

  7. G. Ya. Vanag and E. I. Stankevich, Zh. Obshch. Khim., 3287 (1960).

  8. I. B. Dzvinchuk and N. A. Tolmacheva, Khim. Geterotsikl. Soedin., 554 (2001). [Chem. Heterocycl. Comp., 37, 506 (2001)].

    Google Scholar 

  9. I. B. Dzvinchuk, Khim. Geterotsikl. Soedin., 578 (2007). [Chem. Heterocycl. Comp., 43, 474 (2007)].

  10. I. B. Dzvinchuk and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 585 (2007). [Chem. Heterocycl. Comp., 43, 480 (2007)].

    Google Scholar 

  11. V. M. Potapov, Stereochemistry [in Russian], Khimiya, Moscow (1988), p. 246.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 02094, Ukraine

    I. B. Dzvinchuk

Authors
  1. I. B. Dzvinchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. B. Dzvinchuk.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 101-109, January, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dzvinchuk, I.B. Dearylation with aromatization on cyclocondensation of 4-(dimethyl-amino)benzaldehyde, 2-phenacylaza-heterocycles, and 1,3-[N,C]dinucleophiles. Chem Heterocycl Comp 45, 85–92 (2009). https://doi.org/10.1007/s10593-009-0230-x

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-009-0230-x

Keywords

Search

Navigation