Skip to main content
SpringerLink
Log in

1,2-Oxazoline durch Addition von Trimethylbenzonitriloxid an 2-Hydroxyethylamino-1,4-benzochinone und deren Chinolderivate

1,2-Oxazolines by addition of trimethylbenzonitril oxide to 2-hydroxyethylamino-1,4-quinones and their quinol derivatives

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

Summary

Addition of trimethylbenzonitril oxide to 2-hydroxyethylamino-1,4-quinones and 3,4-dihydro-4-alkyl-8a-methoxy-2H-1,4-benzoxazin-6(8aH)-ones leads to 7,8,9a,9b-tetrahydro-3aH-1,2-oxazolo[4,5-h]-1,4-benzoxazin-4(6H)-ones. In order to determine constitution and conformation of the addition products an NMR-spectroscopic analysis and an X-ray crystal structure analysis of 6-benzyl-9a-hydroxy-3-mesityl-7,8,9a,9b-tetrahydro-3aH-1,2-oxazolo[4,5-h]-31,4-benzoxazin-4-(6H)-one3a were carried out at room temperature: C25H26N2O4,M r=418.49, monoclinic, P21/n,a=13.716(6),b=19.993(6),c=15.348(6) Å, β = 98.55(4)°,V=4162(1)Å3,Z=8,d x=1.336g/cm3,R=6.77%,R w=4.55% (2994 observables, 560 parameters).

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. König K. H. (1959) Chem. Ber.92: 257

    Google Scholar 

  2. McMurtrey K. D., Daves G. D. (1970) J. Org. Chem.35: 4252

    Google Scholar 

  3. Berg H., König K. H., Tresselt D., Wagner H. (1960) Ricera Sci.30 [Suppl. 5]: 1

    Google Scholar 

  4. Rettig H. P., Berg H. (1963) Z. physik. Chem.222: 193

    Google Scholar 

  5. Berg H., Bauer E., Tresselt D. (1960) Advances in Polarography1: 382

    Google Scholar 

  6. Berg H., König K. H. (1958) Anal. Chim. Acta18: 140

    Google Scholar 

  7. Jancke H., Radeglia R., Tresselt D., Berg H. (1977) Z. Chem.17: 105

    Google Scholar 

  8. Huisgen R. (1963) Angew. Chem.75: 742

    Google Scholar 

  9. Kalinowski H. O. (1984)13C-NMR-Spektroskopie. G. Thieme, Stuttgart New York, p. 162

    Google Scholar 

  10. Dähne S., Leupold D. (1972) J. Prakt. Chem.314: 525

    Google Scholar 

  11. Grundmann C., Dean J. M. (1965) J. Org. Chem.30: 2809

    Google Scholar 

  12. Sheldrick G. M. (1986) SHELXS-86, a computer program for crystal structure solution. Univ. of Göttingen, BRD;

    Google Scholar 

  13. Sheldrick G. M. (1976) SHELX-76, a computer program for crystal structure determination. Univ. of Cambridge, England;

    Google Scholar 

  14. DIFABS: Walker N., Stuart D. (1983) Acta Cryst.A39: 158–166;

    Google Scholar 

  15. PLATON: Spek A. L. (1982) In: Sayre D. (ed.), Computational Crystallography. Clarendon Press, Oxford, p. 528;

    Google Scholar 

  16. Johnson C. K. (1965) ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Karl-Franzens-Universität, A-8010, Graz, Österreich

    Manfred Schubert-Zsilavecz & Dagmar Gusterhuber

  2. Institut für Anorganische Chemie, Karl-Franzens-Universität, A-8010, Graz, Österreich

    Ferdinand Belaj

Authors
  1. Manfred Schubert-Zsilavecz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dagmar Gusterhuber
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ferdinand Belaj
    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

Schubert-Zsilavecz, M., Gusterhuber, D. & Belaj, F. 1,2-Oxazoline durch Addition von Trimethylbenzonitriloxid an 2-Hydroxyethylamino-1,4-benzochinone und deren Chinolderivate. Monatsh Chem 121, 555–564 (1990). https://doi.org/10.1007/BF00810865

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00810865

Keywords

Search

Navigation