Skip to main content
Log in

Synthesis of macroheterocycles, analogs of dibenzo-crown compounds. 1. 15-membered oxathiadiamines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Macrocyclic diamides have been synthesized by the condensation of 1,4-bis(2-aminophenyl)-1,4-dioxa(dithia)butanes with the diacid chlorides of glutaric, diglycolic, and thiodiglycolic acids under conditions of high dilution. Subsequent reduction with diborane led to the corresponding macrocyclic diamine containing atoms of oxygen and (or) sulfur. Structural assignments were made using data of mass spectrometry and IR, PMR, and 13C NMR spectra.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. F. Vögtle and E. Weber, Angew. Chem. Int. Ed., 18, 753 (1979).

    Google Scholar 

  2. E. Blasius and K. F. Jansen, in: Topics in Current Chemistry, Vol. 98, Host Guest Complex Chemistry I, Springer, Berlin-Heidelberg-New York (1981), p. 163.

    Google Scholar 

  3. C. J. Pedersen, J. Am. Chem. Soc., 89, 7017 (1967).

    Google Scholar 

  4. G. W. Gokei and S. H. Korzeniowski, Macrocyclic Polyether Syntheses, Berlin-Heidelberg- New York (1982), pp. 168, 280.

  5. H. Stetter and K. H. Meyer, Chem. Ber., 94, 1410 (1961).

    Google Scholar 

  6. T. Doornbos and J. Strating, Synth. Comm., 19, 11 (1971).

    Google Scholar 

  7. P. G. Grimsley, L. F. Lindoy, H. C. Lip, R. J. Smith, and J. K. Baker, Austr. J. Chem., 30, 2095 (1977).

    Google Scholar 

  8. K. R. Adam, L. F. Lindoy, H. C. Lip, J. H. Rea, B. W. Skelton, and A. H, White, J. Chem. Soc. Dalton Trans., 74 (1981).

  9. J. T. Clerk, E. Pretsch, and S. Sternhell, 13C Kernresonanzspektroscopie, Verlagsgesellschaft, Frankfurt am Main (1973), p. 101.

  10. V. M. Bzhezovskii, G. A. Kalabin, I. A. Aliev, B. A. Trofimov, M. A. Shakhgel'diev, and A. M. Kuliev, Izv-. Akad. Nauk SSSR, Ser. Khim., 1999 (1976).

  11. R. D. Cannon, B. Chiswell, and L. M. Venanzi, J. Chem. Soc. A, 1277 (1967).

  12. Sintez Geterotsikl. Soedin., Pt. 6, 34 (1964).

  13. N. G. Luk'yanenko, A. V. Bogatskii, V. A. Shapkin, and Yu. A. Popkov, Zh. Org. Khim., 17, 1069 (1981).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 267–271, February, 1985.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Formanovski, A.A., Murakhovskaya, A.S. Synthesis of macroheterocycles, analogs of dibenzo-crown compounds. 1. 15-membered oxathiadiamines. Chem Heterocycl Compd 21, 225–229 (1985). https://doi.org/10.1007/BF00504214

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00504214

Keywords

Navigation