Synthesis 2009(1): 69-78  
DOI: 10.1055/s-0028-1083237
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Novel Halogenated 4(1H)-Quinolones by Thermolysis of Arylaminomethylene-1,3-dioxane-4,6-diones

Sven Rotzolla, Helmut Reinkea, Christine Fischerb, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 13 July 2008
Publication Date:
01 December 2008 (online)

Abstract

A variety of novel 4(1H)-quinolone derivatives were prepared by thermolysis of aminomethylene Meldrum’s acid derivatives.

    References

  • 1 Cimino G. de Rosa S. deStefano S. Spinelli A. Sodano G. Tetrahedron Lett.  1984,  25:  2925 
  • 2 Molinski TF. Faulkner DJ. Tetrahedron Lett.  1988,  29:  2137 
  • 3 Royt PW. Honeychuk RV. Ravich V. Ponnaluri P. Pannel LK. Buyer JS. Chandhoke V. Stalick WM. de Sesso LC. Donohue S. Ghei R. Releya JD. Ruiz R. Bioorg. Chem.  2001,  29:  387 
  • 4 Jaquemond-Collet I. Bessiere JM. Hannedouche S. Bertrand C. Fouraste I. Moulis C. Phytochem. Anal.  2001,  12:  312 
  • 5 Wentland MP. Perni RB. Dorff PH. Brundage RP. Castaldi MJ. Bailey TR. Carabateas PM. Bacon ER. Young DC. Woods MG. Rosi D. Drozd ML. Kullnig RK. Dutko FJ. J. Med. Chem.  1993,  36:  1580 
  • 6 Schmidt RD. Taschenatlas der Biotechnologie und Gentechnik   Wiley-VCH Verlag; Weinheim: 2002. 
  • 7a Legros JY. Primault G. Fiaud JC. Tetrahedron  2001,  57:  2507 
  • 7b Walker SD. Barder T. Martinelli JR. Buchwald SL. Angew. Chem. Int. Ed.  2004,  43:  1871 
  • 7c Wolf C. Kovi KE. Eur. J. Org. Chem.  2006,  1917 
  • 7d Graf GI. Hastreiter D. da Silva LE. Rebelo RA. Montalban AG. McKillop A. Tetrahedron  2002,  58:  9095 
  • 8 Price CC. Roberts RM. J. Am. Chem. Soc.  1946,  68:  1204 
  • 9 Biere H. Seelen W. Liebigs Ann. Chem.  1976,  1972 
  • 10 Heindel ND. Kennewell PD. Fish VB. J. Heterocycl. Chem.  1969,  6:  77 
  • 11 inventors; British Patent  1147760. Sterling Drug Inc.  ; Chem. Abstr. 1969, 71, 49967a
  • 12 Cassis R. Tapia R. Valderrama JA. Synth. Commun.  1985,  15:  125 
  • 14a Beifuss U. Schniske U. Feder G. Tetrahedron  2001,  57:  1005 
  • 14b Kocienski PJ. Protecting Groups   Thieme; Stuttgart: 1994. 
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CCDC-695059 (3d), CCDC-695060 (4o) and CCDC-695061 (6c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.