Skip to main content
SpringerLink
Log in

Direct arylation of tetrazolo[1,5-a]pyridine and its benzenologues

Direkte Arylierung von Teterazolo[1,5-a]pyridin und dessen Benzologen (Kurze Mitteilung)

Short communication

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Diphenyliodonium fluoroborate proved to be a suitable reagent for direct arylation of bridge head nitrogen containing fused heteroaromatic systems. By this one step method, 1-aryl-tetrazolo[1,5-a]pyridinium salt (3) can be obtained. Arylation of related benzenologues gave not only 1-aryl but also 2-aryltetrazolium salts.

Zusammenfassung

Kondensierte Heteroaromaten mit Brückenkopf-Stickstoff können direkt mit Diphenyl-Jodonium Fluoroborat aryliert werden. In dieser Weise wird 1-Aryltetrazolo[1,5-a]pyridinium Salz (3) in einer Reaktionsstufe synthetisiert. Arylierung der verwandten Benzologen führten nicht nur zu 1-Aryl, sondern auch zu 2-Aryltetrazolium Salzen.

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

References

  1. Fused azolium salts. Part VII. For Part VI see:Hajós Gy., Messmer A., J. Heterocycl. Chem.21, 809 (1984).

    Google Scholar 

  2. Gelléri A., Radics L., Messmer A., Nagy S., Tetrahedron Lett.21, 663 (1980).

    Google Scholar 

  3. Messmer A.,Gelléri A.,Hajós Gy., Symp. on Ambient Reactivity of Conjugated Systems, Salford, 1973. Abstract of Papers, p. 53.

  4. Anderson S.,Glover E.,Vaughan K. D., J. Chem. Soc. Perkin I.1975, 1232.

  5. Makarova L. G.,Nesmeyanov A. N., Izvest. Akad. Nauk. SSSR1945, 617.

  6. Varvoglis A., Synthesis1984, 709.

  7. Nesmeyanov A. N., Makarova L. G., Tolstaya T. P., Tetrahedron1, 145 (1957).

    Google Scholar 

  8. Messmer A., Gelléri A., Angew. Chem.77, 171 (1965).

    Google Scholar 

  9. Messmer A.,Gelléri A.,Hajós Gy., Eur. Symp. of Organic Chem. II, Stresa (Italy) 1981, Abstract of Papers, p. 155.

  10. Messmer A., Hajós Gy., J. Org. Chem.46, 843 (1981).

    Google Scholar 

  11. 3-Phenyltetrazolo[5,1—a]isoquinolinium and 1-phenyltetrazolo[1,5—a]-quinolinium salts, when treated with sodium carbonate or sodium dithionate, result in rapid nitrogen evolution or immediate formation of hetaryl triazene, respectively.

  12. Duffin G. F., Adv. Heterocycl. Chem.3, 38 (1964).

    Google Scholar 

  13. Paudler W. W., Brumbaugh R. J., J. Heterocycl. Chem.5, 2929 (1968).

    Google Scholar 

  14. Beringer F. M., J. Phys. Chem.60, 141 (1956).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Central Research Institute for Chemistry, Hungarian Academy of Sciences, H-1525, Budapest, Hungary

    András Messmer, György Hajós, Judit Fleischer & Mátyás Czugler

Authors
  1. András Messmer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. György Hajós
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Judit Fleischer
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mátyás Czugler
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Messmer, A., Hajós, G., Fleischer, J. et al. Direct arylation of tetrazolo[1,5-a]pyridine and its benzenologues. Monatsh Chem 116, 1227–1231 (1985). https://doi.org/10.1007/BF00811256

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00811256

Keywords

Search

Navigation