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Synthesis 2011(4): 619-625
DOI: 10.1055/s-0030-1258402
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’
Further Information
Received
1 November 2010
Publication Date:
12 January 2011 (online)
Publication History
Publication Date:
12 January 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.
Key words
furan - one-pot synthesis - supported reagents
- 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