Synthesis 2003(14): 2221-2225  
DOI: 10.1055/s-2003-41067
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Unsymmetrical β-Enamino Ketones

Atanas P. Venkov*, Plamen A. Angelov
Department of Organic Chemistry, University of Plovdiv, 24 ‘Tsar Asen’ str., 4000 Plovdiv, Bulgaria
e-Mail: angelov@argon.acad.bg;
Weitere Informationen

Publikationsverlauf

Received 21 May 2003
Publikationsdatum:
24. September 2003 (online)

Abstract

A convenient procedure for modification of β-enaminones by α-C-acylation and subsequent acidic cleavage is described. The unsymmetrical β-enamino ketones obtained in this way could be hydrolyzed to provide an entry towards various unsymmetrical 1,3-diketones.

    References

  • 2a Greenhill JV. Chem. Soc. Rev.  1977,  6:  277 
  • 2b Lue P. Greenhill JV. Adv. Heterocycl. Chem.  1996,  67:  207 
  • 2c Michael JP. De Koning CB. Gravestock D. Hosken GD. Howard AS. Jungmann CM. Krause RWM. Parsons AS. Pelly SC. Stanbury TV. Pure Appl. Chem.  1999,  71:  979 
  • 2d Katritzky AR. Barcock RA. Long QH. Balasubramanian M. Malhotra N. Greenhill JV. Synthesis  1993,  233 
  • 3a Bartoli G. Cimarelli C. Palmieri G. Bosco M. Dalpozzo R. Synthesis  1990,  895 
  • 3b Katritzky AR. Fang Y. Donkor A. Xu J. Synthesis  2000,  2029 
  • 4a Venkov AP. Angelov PA. Synth. Commun.  2003,  33:  3025 
  • 5a Tietze LF. Wichmann J. Chem. Ber.  1992,  2571 
  • 5b Tietze LF. Wichmann J. Liebigs Ann. Chem.  1992,  1063 
  • 6a Kozerski L. Tetrahedron  1976,  1299 
  • 6b Alt GH. Speziale AJ. J. Org. Chem.  1964,  798 
  • 6c Burgemeister T. Dannhardt G. Eibler E. Paulus B. Ziereis K. Arch. Pharm. (Weinheim, Ger.)  1988,  345 
  • 8a Dudek GO. Volpp GP. J. Am. Chem. Soc.  1963,  2697 
  • 8b Dudek GO. Holm RH. J. Am. Chem. Soc.  1962,  2691 
  • 9a Ringel C. Mayer R. J. Prakt. Chem.  1964,  333 
  • 9b Morris ML. Koob RD. Org. Mass Spectrom.  1982,  17:  503 
  • 9c Walker HG. Hauser CW. J. Am. Chem. Soc.  1946,  68:  2742 
  • 9d Hoehn H. inventors; US Patent  4273776. 
  • 10 Boehme H. Traenka M. Z. Chem.  1985,  25:  21 
1

Dr Atanas Venkov passed away suddenly on July 21st, 2003, aged 62.

7

The phosphoric acid used in these experiments was obtained by adding P2O5 (39.4 g) to 85% H3PO4 (d = 1.7, 58.82 mL/100 g).