Monatshefte für Chemie / Chemical Monthly

, Volume 116, Issue 8–9, pp 979–994 | Cite as

Synthese von 3,3a-Dihydro-2H,5H-azeto[2,1-b]benzo[d]1,3-oxazin-2,5-dionen, 2. Mitt.

  • Karl-Hans Ongania
  • Josef Egerbacher
Organische Chemie And Biochemie

Synthesis of 3,3a-dihydro-2H-5H-azeto[2,1-b]benzo[d]-1,3-oxazin-2,5-diones, II

Abstract

Starting from the thioformimidates4 a, b, c and substituted acetylchlorides, the 3R*/4S* 4-methylthio-2-azetidinones5, 13 a, b, c are synthesized.5 is dehalogenated to6. Debenzylation of6 leads to7 and10, which undergo ring closure to9 and12 by the action of chlorine inDME. Hydrazinolysis of13 a, b, c and acylation of the intermediates14 a, b, c afford15 a, b, c. Removal of the protective groups leads to16 d, e, f. The diastereomeric mixtures17 d, e, f, which are obtained by the chlorolysis of16 d, e, f, undergo ring closure to the 3R*/4S* isomers of the title compounds18 d, e, f either spontaneously or by action of silvertetrafluoroborate/silveroxide. Chlorolysis of19 yields the diastereomeric mixture20. Treatment of20 with silvertetrafluoroborate/silveroxide gives21 and22.

Keywords

1-(Carboxyaryl)-4-methylthio-3-phenoxyacetylamino-2-azetidinones 1-(Carboxyaryl)-4-methylthio-3-phthalimido-2-azetidinones Chlorolysis Silveroxide Silvertetrafluoroborate 

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Literatur

  1. 1.
    Mitt.:Ongania K. H., Schwarzenbrunner U., Humer K., Monatsh. Chem.115, 215 (1984).Google Scholar
  2. 2.
    Seno Y.,Yoshioka M., J. C. S. Chem. Comm.1980, 1069;Norasida M.,Yoshida T.,Nagata W., J. Med. Chem.22, 756 (1979).Google Scholar
  3. 3.
    Sheehan J. C., Ben-Ishai D., Piper J. U., J. Amer. Chem. Soc.95, 3064 (1973).Google Scholar
  4. 4.
    Neuere Übersichten:Bose A. K., Rham B., Manhas, in: Stereoselektive Synthesis of Natural Products (Bartmann W., Winterfeld E., Hrsg.), 1. Aufl., S. 181. Amsterdam-Oxford: Excerpta Medica. 1977.Isaacs N. S., Q. Rev., Chem. Soc.1976, 181;Mukerjee A. K., Singh A. K., Tetrahedron34, 1731 (1978).Google Scholar
  5. 5.
    Lattrell R.,Lohaus G., Liebigs Ann. Chem.1974, 870 und dort zitierte Literatur.Google Scholar
  6. 6 a).
    Clauß K.,Grimm D.,Prossel G., Liebigs Ann. Chem.1974, 539;Google Scholar
  7. 6 b).
    Bachi M. D., Breiman R., J. C. S. Perkin I 1980, 11;Google Scholar
  8. 6 c).
    Bachi M. D.,Sasson S.,Vaya J., J. C. S. Perkin1980, 2228;Google Scholar
  9. 6 d).
    Kukolja S., J. Amer. Chem. Soc.93, 6267 (1971);Google Scholar
  10. 6 e).
    Hoppe D.,Klaft M., Liebigs Ann. Chem.1980, 1527, und dort zitierte Literatur.Google Scholar
  11. 7.
    Kukolja S., Lammert S. R., J. Amer. Chem. Soc.97, 5582 (1975).Google Scholar

Copyright information

© Springer-Verlag 1985

Authors and Affiliations

  • Karl-Hans Ongania
    • 1
  • Josef Egerbacher
    • 1
  1. 1.Institut für Organische und Pharmazeutische ChemieUniversität InnsbruckInnsbruckÖsterreich

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