Download PDF
Synthesis 2003(2): 0227-0232
DOI: 10.1055/s-2003-36827
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Functionalized 4H-Pyran and Cyclohexanone Derivatives via Three-Component Reactions of Dimethyl Acetonedicarboxylate, Aromatic Aldehydes­, and Malononitrile

Dieter Heber*a, Edmont V. Stoyanov*b
Department of Pharmaceutical Chemistry, University of Kiel, Gutenbergstr. 76, 24118 Kiel, Germany
Fax: +49(431)8801118; e-Mail: dheber@pharmazie.uni-kiel.de;
Department of Industrial Pharmacy, Faculty of Pharmacy, Medical University of Sofia, Dunav 2, 1000 Sofia, Bulgaria
e-Mail: estoyanov@yahoo.com;
Further Information

Publication History

Received 30 September 2002
Publication Date:
22 January 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

Dependent on the reaction time, the three-component condensation of dimethyl acetonedicarboxylate (1), aromatic aldehydes 2, and malononitrile (3) gives rise to 4H-pyran derivatives 5 after reflux for 15 min. Moreover, using excess of benzaldehyde and prolonged heating for 150 min afforded multifunctional cyclohexanone derivatives 8. Different substitution patterns in the phenyl nucleus of 8 can be achieved by condensation of 4H-pyran derivatives 5 with benzaldehydes 2.

Key words

heterocycles - carbocycles - Michael additions - rearrangements - cyclizations - condensation

    References

  • 1 Gurevich AI. Dobrynin VN. Kolosov MN. Popravko SA. Riabova ID. Antibiotiki (Moscow)  1971,  16:  510 ; Chem. Abstr. 1971, 75, 95625
    Google Scholar
  • 2 Bystrov NS. Tetrahedron Lett.  1975,  32:  2791 
    Google Scholar
  • 3 Brondz I. Tetrahedron Lett.  1982,  32:  1299 
    Google Scholar
  • 4 Berghöfer R. Dissertationes Botanicae   Verlag J. Cramer; Berlin, Stuttgart: 1987.  p.106 
    Google Scholar
  • 5 Maisenbacher P. Dissertation   Universität Tübingen; Germany: 1991. 
    Google Scholar
  • 6 House H. Wickham P. Mueller H. J. Am. Chem. Soc.  1962,  84:  3139 
    CrossrefGoogle Scholar
  • 7 Mannich C. Mohs P. Chem. Ber.  1930,  63:  608 
    Google Scholar
  • 8 Mannich C. Veit F. Chem. Ber.  1935,  68:  506 
    Google Scholar
  • 9 Haensel W. Haller R. Arch. Pharm. (Weinheim, Ger.)  1970,  303:  334 
    Google Scholar
  • 10 Abed NM. Hafez EAA. Elsakka I. Ibrahim MH. J. Heterocycl. Chem.  1984,  21:  1261 
    Google Scholar
  • 11 Ibrahim NS. Heterocycles  1986,  24:  935 
    Google Scholar
  • 12 El-Sakka IA. El-Kousy SM. J. Prakt. Chem.  1991,  332:  345 
    Google Scholar
  • 13 Martin N. Quinterio M. Seoane C. Albert A. Cano FH. Abramovich R. Tetrahedron  1992,  48:  1581 
    CrossrefGoogle Scholar
  • 14 Elnagdi MH. Abdel-Motaleb RM. Mustafa M. Zayed MF. Kamel EM. J. Heterocycl. Chem.  1987,  24:  1677 
    Google Scholar
  • 15 Soto JL. Seoane C. Martin N. Blanco L. Heterocycles  1983,  20:  803 
    Google Scholar
  • 16 Ciller JA. Martin N. Seoane C. Soto JL. J. Chem. Soc., Perkin Trans. 1  1985,  2581 
    CrossrefGoogle Scholar
  • 17 Abed NM. Ibrahim NS. Elnagdi MH. Z. Naturforsch., B: Anorg. Chem. Org. Chem.  1986,  41:  925 
    Google Scholar
  • 18 Martin N. Seoane C. Soto JL. Tetrahedron  1988,  44:  5861 
    CrossrefGoogle Scholar
  • 19 Marguan MM. Martin N. Seoane C. Soto JL. J. Liebigs Ann. Chem.  1989,  145 
    Google Scholar
  • 20 Martin N. Quinteiro M. Seoane C. Tetrahedron  1992,  48:  1581 
    CrossrefGoogle Scholar
  • 21 Martinez-Grau A. Marco JL. Bioorg. Med. Chem. Lett.  1997,  7:  3165 
    CrossrefGoogle Scholar
  • 22 O’Callaghan CN. McMurry TBH. J. Chem. Res. Miniprint  1999,  8:  2179 
    Google Scholar
  • 23 DeLucas AI. Fernandez-Gadea J. Martin N. Seoane C. Tetrahedron  2001,  57:  5591 
    CrossrefGoogle Scholar
  • 24 Rowland AT. Filla SA. Coutlangus MD. Winemiller MD. Chamberlin MJ. Czulada G. Johnson SD. J. Org. Chem.  1998,  63:  4359 
    CrossrefGoogle Scholar
  • 25 Eliel EL. Wilen SH. Mander LN. Stereochemistry of Organic Compounds   Wiley; New York: 1994.  p.726-729  
    Google Scholar
  • 26 Yi-Qun L. J. Chem. Res., Synop.  2000,  11:  524 
    Google Scholar