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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 4
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Original Articles

Antimony Trichloride: An Efficient and Mild Catalyst for Cyclization of 2-Aminochalcones to the Corresponding 2-Aryl-2,3-Dihydroquinolin-4(1H)-ones

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Pages 476-481 | Received 23 Jan 2009, Published online: 03 Feb 2010

REFERENCES

  • Kalinin , V. N. ; Shostakovsky , M. V. ; Ponomaryov , A. B. A new route to 2-aryl-4-quinolones via palladium-catalyzed carbonylative coupling of o-iodoanilines with terminal arylacetylenes . Tetrahedron Lett. 1992 , 33 , 373 – 376 .
  • (a) Singh , O. V. ; Kapil , R. S. A new route to 2-aryl-4-quinolones via thallium(III) p-tolylsulphonate-mediated oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones . Synth. Commun. 1993 , 23 , 277 – 283 ; (b) Prakash , O. ; Kumar , D. ; Saini , R. K. ; Singh , S. P. Hypervalent iodine oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones: An easy access to 2-aryl-4-quinolones . Synth. Commun. 1994 , 24 , 2167 – 2172 .
  • Xia , Y. ; Yang , Z.-Y. ; Xia , P. ; Bastow , K. F. ; Tachibana , Y. ; Kuo , S.-C. ; Hamel , E. ; Hackl , T. ; Lee , K.-H. Antitumor agents, 181: Synthesis and biological evaluation of 6–7,2′,3′,4′-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents . J. Med. Chem. 1998 , 41 , 1155 .
  • (a) Torii , S. ; Okumoto , H. ; He-Xu , L. Palladium-catalyzed carbonylation to form 2-substituted 1,4-dihydro-4-oxo-quinoline. Tetrahedron Lett. 1991, 32, 237–240; (b) Homi , O. E. O. ; Peltonen , C. ; Heikkila , L. 2-Aryl-4-quinolones and fused quinolines from β-chloroarylidinemalonates and related chloro esters. J. Org. Chem. 1990, 55, 2513.
  • (a) Donnelly , J. A. ; Farrell , D. F. Chalcone derivatives as precursors of 1,2,3,4-tetrahydro-4-quinolones . Tetrahedron 1990 , 46 , 885 – 894 ; (b) Donnelly , J. A. ; Farrell , D. F. The chemistry of 2′-amino analogs of 2′-hydroxychalcone and its derivatives . J. Org. Chem. 1990 , 55 , 1757 ; (c) Tokes , A. L. ; Litkei , G. Schmidt reaction on 2-aryl-1,2,3,4-tetrahydro-4-quinolone . Synth. Commun. 1993 , 23 , 895 – 902 .
  • (a) Tokes , A. L. ; Szilagyi , L. Resolution of (±)-2,3-dihydro-2-phenyl-4 (1H)-quinolone . Synth. Commun. 1987 , 17 , 1235 – 1245 ; (b) Tokes , A. L. ; Litkei , G. ; Szilagyi , L. N-Heterocycles by cyclization of 2′-NHR-chalcones, 2′-NHR-chalcone dibromides, and 2′-NHR-α-azidochalcones . Synth. Commun. 1992 , 22 , 2433 – 2445 .
  • (a) Varma , R. S. ; Saini , R. K. Microwave-assisted isomerization of 2′-aminochalcones on clay: An easy route to 2-aryl-1,2,3,4-tetrahydro-4-quinolones . Synlett 1997 , 857 – 858 ; (b) Kumar , K. H. ; Muralidharan , D. ; Perumal , P. T. Indium(III) chloride/silica gel–promoted facile and rapid cyclization of 2-aminochalcones to 2-aryl-2,3-dihydroquinolin-4-(1H)-ones under solvent-free conditions . Synthesis 2004 , 63 – 68 .
  • (a) Ahmed , N. ; van Lier , J. E. Silica-gel-supported TaBr5: New catalyst for the facile and rapid cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 2725 – 2729 ; (b) Ahmed , N. ; van Lier , J. E. Alumina-supported CeCl3 · 7H2O-NaI: An efficient catalyst for the cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions . Tetrahedron Lett. 2007 , 48 , 13 – 15 , and reference cited therein.
  • (a) Maiti , G. ; Kundu , P. Imino Diels–Alder reactions: An efficient one-pot synthesis of pyrano and furanoquinoline derivatives catalyzed by SbCl3 . Tetrahedron Lett. 2006 , 47 , 5733 – 5736 ; (b) Maiti , G. ; Kundu , P. Antimony trichloride–catalyzed Michael addition of indoles to the α,β-unsaturated ketones . Synth. Commun. 2007 , 37 , 2309 .

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