Skip to main content
SpringerLink
Log in

Über Reaktionen cyclischer Oxalylverbindungen, 7. Mitt.

Reactions of cyclic oxalyl compounds, VII: Syntheses of heterocycles, CLXIII

Synthesen von Heterocyclen, 163. Mitt.

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

Abstract

Benzamide oxime reacts with oxalyl chloride (molar rate 2∶1) to give the oxadiazino-oxadiazine derivative3. Benzamide oxime O-ethers and oxalyl chloride cyclize in boiling xylene yielding 3-phenyl-4.5-dihydro-1.2.4-oxadiazol-5-one (7) or5, depending on the reaction time. The imidazolium salt4 is postulated as the common intermediate.

Zusammenfassung

Benzamidoxim reagiert mit Oxalylchlorid zum Oxadiazino-oxadiazin-Derivat3. Benzamidoxim-äther und Oxalylchlorid cyclisieren sich je nach Reaktionsdauer in siedendem Xylol über das entsprechende Imidazolium-Salz4 entweder zum 3-Phenyl-4,5-dihydro-1,2,4-oxadiazol-5-on (7) oder, wie im Falle des Äthyl-äthers, zur Verbindung5 (C11H12N2O2).

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. F. Eloy undR. Lenaers, Chem. Rev.62, 166 (1962).

    Google Scholar 

  2. O. Schulz, Ber. dtsch. chem. Ges.18, 2458 (1885).

    Google Scholar 

  3. F. Tiemann, Ber. dtsch. chem. Ges.18, 1060 (1885).

    Google Scholar 

  4. F. Tiemann, Ber. dtsch. chem. Ges.19, 1457 (1886).

    Google Scholar 

  5. A. Wurm, Ber. dtsch. chem. Ges.22, 3130 (1889).

    Google Scholar 

  6. E. Ziegler, A. Argyrides undW. Steiger, Mh. Chem.102, 301 (1971).

    Google Scholar 

  7. J. Goerdeler undR. Sappelt, chem. Ber.100, 2064 (1967).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie der Universität Graz, Graz, Österreich

    E. Ziegler, G. Kollenz & H. Igel

Authors
  1. E. Ziegler
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Kollenz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. Igel
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Herrn Prof. Dr.H. Kämmerer, Universität Mainz, mit freundschaftlichen Grüßen zum 60. Geburtstag gewidmet.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ziegler, E., Kollenz, G. & Igel, H. Über Reaktionen cyclischer Oxalylverbindungen, 7. Mitt.. Monatshefte für Chemie 103, 599–604 (1972). https://doi.org/10.1007/BF00904963

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00904963

Search

Navigation