Skip to main content
SpringerLink
Log in

Aminomethylation of 2-(2-furyl)imidazo-[1,2-a]pyridine

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The aminomethylation (morpholino- and piperidinomethylation) of 2-(2-furyl)imidazo[1,2-a]-pyridine proceeds primarily at the 3 position of the imidazopyridine system at equimolecular ratios of the reagents, but also proceeds at the 5 position of the furan ring when there is a slight excess of formaldehyde and amine. The structure of the product of monomorpholinomethylation was proved by nitration to give a mononitro derivative that was identical to the 3-morpholinomethyl-2-(5-nitro-2-furyl)imidazo[1,2-a]pyridine prepared by the morpholinomethylation of 2-(5-nitro-2-furyl)imidazo[1,2-a]pyridine. Thin-layer chromatography and IR and UV spectroscopy were used to prove the structures.

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

Literature cited

  1. J. G. Lombardino, J. Org. Chem., 30, 2403 (1965).

    Google Scholar 

  2. J. P. Paolini and R. K. Robins, J. Org. Chem., 30, 4085 (1965).

    Google Scholar 

  3. L. Almirante, L. Polo, A. Mugnaini, et al., J. Med. Chem., 8, 305 (1965).

    Google Scholar 

  4. R. F. Holdren and R. M. Hixon, J. Am. Chem. Soc., 68, 1198 (1946).

    Google Scholar 

  5. E. L. Eliel and M. T. Fisk, Organic Syntheses, Vol. 35 (1955), p. 78.

    Google Scholar 

  6. H. E. Winberg, F. S. Fawcett, W. E. Mochel, and C. W. Theobald, J. Am. Chem. Soc., 82, 1428 (1960).

    Google Scholar 

  7. R. F. Holdren, J. Am. Chem. Soc., 69, 464 (1947).

    Google Scholar 

  8. L. I. Vereshchagin, R. I. Katkevich, and S. P. Korshunov, Khim. Geterotsikl. Soedin., 12 (1967).

  9. N. O. Saldabol, A. Ya. Medne, and S. A. Giller, Chemistry of Five-Membered Nitrogen Heterocycles [in Russian], Rostov-on-Don (1966), p. 151.

  10. N. O. Saldabol and I. B. Mazheika, Khim. Geterotsikl. Soedin., 118 (1969).

  11. N. O. Saldabol, L. N. Alekseeva, B. A. Brizga, L. V. Kruzmetra, and S. A. Giller, Khim.-Farmats. Zh., No. 7, 20 (1970).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, Riga

    N. O. Saldabol, L. L. Zeligman & S. A. Giller

Authors
  1. N. O. Saldabol
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. L. Zeligman
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. A. Giller
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 818–821, June, 1971.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Saldabol, N.O., Zeligman, L.L. & Giller, S.A. Aminomethylation of 2-(2-furyl)imidazo-[1,2-a]pyridine. Chem Heterocycl Compd 7, 763–766 (1971). https://doi.org/10.1007/BF00476829

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00476829

Keywords

Search

Navigation