Synthesis 2011(4): 619-625  
DOI: 10.1055/s-0030-1258402
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Furans Using Base- and Acid-Supported Reagents ‘Na2CO3/Al2O3-PPA/SiO2

Tadashi Aoyama*a,b, Takashi Nagaokaa, Toshio Takidoa, Mitsuo Kodomaric
a Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
Fax: +81(3)32590818; e-Mail: [email protected];
b The Center for Creative Materials Research, Research Institute of Science and Technology, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
c Department of Bioscience and Engineering, Shibaura Institute of Technology, Fukasaku, Minuma-ku, Saitama 337-8570, Japan
Weitere Informationen

Publikationsverlauf

Received 1 November 2010
Publikationsdatum:
12. Januar 2011 (online)

Abstract

A convenient method for the one-pot synthesis of furans from β-keto esters and α-halo ketones was developed using an acid- and base-supported reagent system ‘Na2CO3/Al2O3-PPA/SiO2’. The condensation reaction of triketones, which are formed from the reaction of β-keto esters with α-halo ketones in the presence of Na2CO3/Al2O3, was promoted by PPA/SiO2 to give the corresponding furans in good yields. This method is simple and easy to perform in comparison with stepwise processes, and the yields are good.

    References

  • 1 Lipshutz BH. Chem. Rev.  1986,  86:  795 
  • 2 Lansiaux A. Dassonneville L. Facompré M. Kumar A. Stephens CE. Bajic M. Tanious F. Wilson WD. Boykin DW. Bailly C. J. Med. Chem.  2002,  45:  1994 
  • 3 Nakanishi K. Natural Products Chemistry   Kodansha Ltd.; Tokyo: 1974. 
  • 4 Hou XL. Cheung HY. Hon TY. Kwan PL. Lo TH. Tong SY. Wong HNC. Tetrahedron  1998,  54:  1995 
  • 5 Kürt L. Czakó B. Strategic Applications of Named Reactions in Organic Synthesis   Elsevier Academic; Amsterdam: 2005. 
  • 6 Stauffer F. Neier R. Org. Lett.  2000,  2:  3535 
  • 7 Christopfel WC. Miller L. J. Org. Chem.  1986,  51:  4169 
  • 8 Bambury RE. Yaktin HK. Wyckoff KK. J. Heterocycl. Chem.  1968,  5:  95 
  • 9 Chochois H. Sauthier M. Maerten E. Castanet Y. Mortreux A. Tetrahedron  2006,  62:  11740 
  • 10 Aoyama T. Takido T. Kodomari M. Synlett  2005,  2739 
  • 11 Aoyama T. Orito M. Takido T. Kodomari M. Synthesis  2008,  2089 
  • 12 Aoyama T. Okada K. Nakajima H. Matsumoto T. Takido T. Kodomari M. Synlett  2007,  387 
  • 13 Alagoz O. Yilmaz M. Tarik PA. Synth. Commun.  2006,  36:  1005 
  • 14 Lutz R. McGinn CE. Bailey PS. J. Am. Chem. Soc.  1943,  65:  843 
  • 15 Davies HML. Romines KR. Tetrahedron  1988,  44:  3343 
  • 16 Wang G. Guan Z. Tang R. He Y. Synth. Commun.  2010,  40:  370 
  • 17 Babudri F. Cicco SR. Farinola GM. Lopez LC. Naso F. Pinto V. Chem. Commun.  2007,  3756