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Synthesis 2010(16): 2794-2798
DOI: 10.1055/s-0030-1258146
DOI: 10.1055/s-0030-1258146
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed One-Pot Synthesis of Substituted Benzimidazo[1,2-a]quinolines
Further Information
Received
19 March 2010
Publication Date:
01 July 2010 (online)
Publication History
Publication Date:
01 July 2010 (online)

Abstract
A one-pot procedure for the synthesis of substituted benzimidazo[1,2-a]quinolines from the corresponding benzimidazoles and 2-bromobenzaldehydes has been developed. The titled products were prepared through Knoevenagel condensation and copper-catalyzed intramolecular Ullmann-type coupling in moderate to good yields.
Key words
Knoevenagel condensation - copper catalyst - Ullmann coupling - quinoline synthesis - cascade process
-
1a
Cox O.Jackson H.Vargas VA.Baez A.Gonzalez BC. J. Med. Chem. 1982, 25: 1378 -
1b
Rida SM.Soliman FSG.Badawey E.Kappe T. J. Heterocycl. Chem. 1988, 25: 1725 -
1c
Pastor J.Siro JG.Garcio-Navio JL.Vaquero JJ.Alvarez-Builla J.Gago F.de Pascual-Teresa B.Pastor M.Melia Rodrigo M. J. Org. Chem. 1997, 62: 5476 -
1d
El-Hawash SAM.Badawey E.Kappe T. Pharmazie 1999, 54: 341 -
1e
Katritzky AR.Tymoshenko DO.Monteux D.Vuedensky V.Nikonov G.Cooper CB.Deshpande M. J. Org. Chem. 2000, 65: 8059 -
1f
Demirayak S.Abu Mohsen U.Cagri Karaburun S. Eur. J. Med. Chem. 2002, 37: 255 -
1g
He Y.Yang J.Baogen W.Risen L.Swayze EE. Bioorg. Med. Chem. Lett. 2004, 14: 1217 - 2
Morgan G.Stewart J. J. Chem. Soc. 1938, 1292 -
3a
Hranjec M.Karminski-Zamola G. Molecules 2007, 12: 1817 -
3b
Hranjec M.Kralj M.Karminski-Zamola G. J. Med. Chem. 2007, 50: 5696 - 4
Venkatesh C.Sundaram GSM.Ila H.Junjappa H.
J. Org. Chem. 2006, 71: 1280 - 5
Cai Q.Li Z.-Q.Wei J.-J.Fu L.-B.Ha C.-Y.Pei D.-Q.Ding K. Org. Lett. 2010, 12: 1500 -
6a
Johnson JR. Org. React. 1942, 1: 210 -
6b
Prout FS. J. Org. Chem. 1953, 18: 928 -
6c
Simpson J.Rathbone DL.Billington DC. Tetrahedron Lett. 1999, 40: 7031 -
6d
Ganushchak NI.Lesyuk AI.Fedorovich IS.Obushak ND.Andrushenko VN. Russ. J. Org. Chem. (Engl. Transl.) 2003, 39: 1295 -
6e
Saczewski F.Reszka P.Gdaniec M.Grunert R.Bednarski PJ. J. Med. Chem. 2004, 47: 3438 - For selected examples on ligand-promoted Ullmann-type amination, see:
-
7a
Ma D.Zhang Y.Yao J.Wu S.Tao F. J. Am. Chem. Soc. 1998, 120: 12459 -
7b
Ma D.Xia C. Org. Lett. 2001, 3: 2583 -
7c
Klapars A.Antilla JC.Huang X.Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727 -
7d
Gujadhur RK.Bates CG.Venkataraman D. Org. Lett. 2001, 3: 4315 -
7e
Antilla JC.Klapars A.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684 -
7f
Kwong FY.Buchwald SL. Org. Lett. 2003, 5: 793 -
7g
Ma D.Cai Q.Zhang H. Org. Lett. 2003, 5: 2453 -
7h
Zhang H.Cai Q.Ma D. J. Org. Chem. 2005, 70: 5164 -
7i
Shafir A.Buchwald SL. J. Am. Chem. Soc. 2006, 128: 8742 -
7j
Ma H.Jiang X. J. Org. Chem. 2007, 72: 8943 -
7k
Ma D.Cai Q. Acc. Chem. Res. 2008, 41: 1450 - 8
Büchi J.Zwicky H.Aebi A. Arch. Pharm. (Weinheim, Ger.) 1960, 293: 758