Skip to main content
SpringerLink
Log in

Über einige Umsetzungen von 2,5-Diamino- sowie 2-Amino-1,3,4-thiadiazolen mit α-Halogenketonen zu Imidazo[2,1-b]-1,3,4-thiadiazolen

Some reactions of 2,5-diamino- and 2-amino-1,3,4-thiadiazoles with α-halogen ketones to imidazo[2,1-b]-1,3,4-thiadiazoles

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

Abstract

2,5-Diamino-1,3,4-thiadiazole (1) reacts with α-halogencarbonyl compounds to 2-imino-3-phenacyl(acetonyl)-5-amino-1,3,4-thiadiazolines (3) which easily can be cyclised to 2-amino-6-aryl (alkyl)-imidazo[2,1-b]-1,3,4-thiadiazoles (4), the structure of which was proofed.

On the basis of the amino function in position 2 these substances were able to form easilySchiff bases (5, 6, 7). Their semicyclic amidine system did not allow as yet to integraet it in a third ring system.

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

Literatur

  1. A. Sitte, H. Paul undG. Hilgetag, Z. Chem.7, 341 (1967).

    Google Scholar 

  2. R. Wessel, Dissertation, Humboldt-Univ. Berlin 1970.

  3. A. Sitte, R. Wessel undH. Paul, Mh. Chem.106, 1291 (1975).

    Google Scholar 

  4. G. Pulvermacher, Ber. dtsch. chem. Ges.27, 613 (1894).

    Google Scholar 

  5. M. Freund undC. Meinecke, Ber. dtsch. chem. Ges.29, 2511 (1896).

    Google Scholar 

  6. G. Young undW. Eyre, J. chem. Soc.79, 54 (1901).

    Google Scholar 

  7. T. Matsukawa undS. Ban, J. pharmac. Soc. Japan [Yakugaku Zasshi]72, 610 (1952); zit. nach Chem. Abstr.47, 6409 (1953).

    Google Scholar 

  8. B. Kickhöfen undF. Kröhnke, Chem. Ber.88, 1109 (1955).

    Google Scholar 

  9. J. Goerdeler undW. Roth, Chem. Ber.96, 534 (1963).

    Google Scholar 

  10. H. Beyer undA. Hetzheim, Chem. Ber.97, 1031 (1964).

    Google Scholar 

  11. G. Weber undF. Maggio, Ann. Chimica52, 747 (1962).

    Google Scholar 

  12. T. Pyl, F. Waschk undH. Beyer, Ann. Chem.663, 113 (1963).

    Google Scholar 

  13. H. Paul undA. Sitte, Mh. Chem.102, 550 (1971).

    Google Scholar 

  14. S. Ban, J. pharmac. Soc. Japan [Yakugaku Zasshi]74, 658 (1954); Chem. Abstr.48, 10740 (1954).

    Google Scholar 

  15. A. Hantzsch undO. Schwab, Ber. dtsch. chem. Ges.34, 822 (1901).

    Google Scholar 

  16. G. Barnikow undJ. Bödeker, J. prakt. Chem.313, 1148 (1971); dort weitere Lit.-Hinweise.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Sektion Chemie, Humboldt-Universität zu Berlin, Hessische Straße 1/2, DDR-1040, Berlin, Deutsche Demokratische Republik

    Heinz Paul, Adolf Sitte & Rolf Wessel

Authors
  1. Heinz Paul
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Adolf Sitte
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rolf Wessel
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

8. Mitt. über Heterocyclen; 7. Mitt.:A. Sitte, R. Wessel undH. Paul, Mh. Chem.106, 1291 (1975).

Rights and permissions

Reprints and permissions

About this article

Cite this article

Paul, H., Sitte, A. & Wessel, R. Über einige Umsetzungen von 2,5-Diamino- sowie 2-Amino-1,3,4-thiadiazolen mit α-Halogenketonen zu Imidazo[2,1-b]-1,3,4-thiadiazolen. Monatshefte für Chemie 108, 665–680 (1977). https://doi.org/10.1007/BF00912812

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00912812

Search

Navigation