Skip to main content
SpringerLink
Log in

Novel synthesis and reactions of 1,4,7-trimethyl-4,5,7,8-tetrahydro-6h-imidazo[4,5-e][1,4]diazepine-5,8-dione—a cyclic caffeine analog

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The synthesis of a cyclic homolog of caffeine is reported. Its 2-nitro- and 2-amino derivatives were obtained for the first time. It was shown that the 2-bromo and 2-chloro substituted cyclic homologs react with nucleophiles under basically identical conditions. Whereas 8-bromocaffeine can give a normal Ullman reaction product via heating with powdered copper in ethylene glycol, the homolog gives only a reduction product and does not react with potassium thiocyanate or cyanide.

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. K. Isshiki, Y. Takahashi, H. Iinuma, H. Naganawa, J. Umezawa, T. Takeuchi, H. Umezawa, S. Nishimura, N. Okada, and K. Tatsuta, J. Antibiot.,40, 1461 (1987).

    Google Scholar 

  2. T. Fujii, T. Saito, and T. Fujisawa, Heterocycles,27, 1163 (1988).

    Google Scholar 

  3. P. K. Bridson, Heterocycles,38, 1007 (1994).

    Google Scholar 

  4. É. I. Ivanov, A. V. Bogatskii, and K. S. Zakharov, Dokl. Akad. Nauk,255, 591 (1980).

    Google Scholar 

  5. A. V. Bogatskii and É. I. Ivanov, Ukr. Khim. Zh., No. 10, 1074 (1980).

    Google Scholar 

  6. É. I. Ivanov, G. D. Kalayanov, and I. M. Yaroshchenko, Khim. Geterotsikl. Soedin., No. 7, 955 (1992).

    Google Scholar 

  7. R. Elderfield (ed.), Heterocyclic Compounds, [Russian translation], Vol. 8, Mir, Moscow (1969), p. 955.

    Google Scholar 

Download references

Authors
  1. É. I. Ivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

A. V. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, Odessa 270080. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 824–827, June, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ivanov, É.I. Novel synthesis and reactions of 1,4,7-trimethyl-4,5,7,8-tetrahydro-6h-imidazo[4,5-e][1,4]diazepine-5,8-dione—a cyclic caffeine analog. Chem Heterocycl Compd 34, 719–722 (1998). https://doi.org/10.1007/BF02252283

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02252283

Keywords

Search

Navigation