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Synthesis 2004(14): 2381-2385
DOI: 10.1055/s-2004-831185
DOI: 10.1055/s-2004-831185
PAPER
© Georg Thieme Verlag Stuttgart · New York
Silver Phosphotungstate: A Novel and Recyclable Heteropoly Acid for Friedländer Quinoline Synthesis
Further Information
Received
26 March 2004
Publication Date:
19 August 2004 (online)
Publication History
Publication Date:
19 August 2004 (online)
Abstract
o-Aminoaryl ketones undergo smooth condensation with α-methylene ketones on the surface of silver heteropoly acid (Ag3PW12O40) under mild reaction conditions to afford the corresponding polysubstituted quinolines in excellent yields with high selectivity. The catalyst can be recovered by simple filtration and can be recycled in subsequent reactions.
Keywords
heteropoly acids - o-aminoaryl ketones - α-methylene ketones - quinolines
-
1a
Larsen RD.Corley EG.King AO.Carrol JD.Davis P.Verhoeven TR.Reider PJ.Labelle M.Gauthier JY.Xiang YB.Zamboni RJ. J. Org. Chem. 1996, 61: 3398 -
1b
Chen YL.Fang KC.Sheu J.-Y.Hsu SL.Tzeng CC. J. Med. Chem. 2001, 44: 2374 -
1c
Roma G.Braccio MD.Grossi G.Mattioli F.Ghia M. Eur. J. Med. Chem. 2000, 35: 1021 -
2a
Kalluraya B.Sreenivasa S. Farmaco 1998, 53: 399 -
2b
Doube D.Blouin M.Brideau C.Chan C.Desmarais S.Eithier D.Falgueyret JP.Friesen RW.Girard M.Girard Y.Guay J.Tagari P.Young RN. Bioorg. Med. Chem. Lett. 1998, 8: 1255 - 3
Maguire MP.Sheets KR.McVety K.Spada AP.Zilberstein A. J. Med. Chem. 1994, 37: 2129 -
4a
Agarwal AK.Jenekhe SA. Macromolecules 1991, 24: 6806 -
4b
Zhang X.Shetty AS.Jenekhe SA. Macromolecules 1999, 32: 7422 -
4c
Zhang X.Shetty AS.Jenekhe SA. Macromolecules 2000, 33: 2069 -
4d
Jenekhe SA.Lu L.Alam MM. Macromolecules 2001, 34: 7315 -
5a
Jones G. In Comprehensive Heterocyclic Chemistry II Vol. 5:Katritzky AR.Rees CW.Scriven EFV. Pergamon; New York: 1996. p.167 -
5b
Cho CS.Oh BH.Kim TJ.Shim SC. Chem. Commun. 2000, 1885 ; and references cited therein -
5c
Jiang B.Si Y.-C. J. Org. Chem. 2002, 67: 9449 -
6a
Skraup H. Ber. 1880, 13: 2086 -
6b
Friedländer P. Ber. 1882, 15: 2572 -
6c
Mansake RHF.Kulka M. Org. React. 1953, 7: 59 -
6d
Linderman RJ.Kirollos SK. Tetrahedron Lett. 1990, 31: 2689 -
6e
Theoclitou M.-E.Robinson LA. Tetrahedron Lett. 2002, 43: 3907 -
7a
Cheng C.-C.Yan S.-J. Org. React. 1982, 28: 37 -
7b
Thummel RP. Synlett 1992, 1 -
7c
Eckert H. Angew. Chem., Int. Ed. Engl. 1981, 20: 208 -
7d
Gladiali S.Chelucci G.Mudadu MS.Gastaut MA.Thummel RP. J. Org. Chem. 2001, 66: 400 - 8
Fehnel EA. J. Heterocycl. Chem. 1967, 4: 565 -
9a
Strekowski L.Czamy A. J. Fluorine Chem. 2000, 104: 281 -
9b
Hu Y.-Z.Zang G.Thummel RP. Org. Lett. 2003, 5: 2251 -
10a
Kwon TW.Song SJ.Cho SJ. Tetrahedron Lett. 2003, 44: 255 -
10b
McNaughton BR.Miller BL. Org. Lett. 2003, 5: 4257 -
10c
Yadav JS.Reddy BVS.Rao RS.Kumar VN.Nagaiah K. Synthesis 2003, 1610 -
10d
Arkadi A.Chiarini M.Di Giuseppe S.Marinelli F. Synlett 2003, 203 -
10e
Palimkar SS.Siddiqui SA.Daniel T.Lahoti RJ.Srinivasan KV. J. Org. Chem. 2003, 68: 9371 - 11
Clark JH. Acc. Chem. Res. 2002, 35: 791 -
12a
Okuhara T.Mizuno N.Misono M. Appl. Catal. A 2001, 222: 63 -
12b
Kozhevnikov IV. Chem. Rev. 1998, 98: 171 - 13 Preparation of Ag3PW12O40:
Haber J.Pamin K.Matachowski L.Napruszewska B.Poltowicz J. J. Catal. 2002, 207: 296