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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

Facile Iodine(III)-Mediated Approach for the Regioselective Chlorination of 2-Aryl-2,3-dihydro-4(1H)-quinolones

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Pages 596-603 | Received 09 Jun 2008, Published online: 28 Jan 2009

REFERENCES

  • McBee , E. T. ; Hass , H. B. Developments in the chlorination of satrurated hydrocarbons . Ind. Eng. Chem. 1943 , 33 , 137 .
  • Neale , R. S. ; Sehepers , R. G. ; Walsh , M. R. The chlorination of reactive anilines . J. Org. Chem. 1964 , 29 , 3390 .
  • Nilkson , T. E. ; Roche-Dolson , C. A. A convenient procedure for the chlorination of deactivated anilines . Synthesis 1985 , 669 .
  • (a) Varvoglis , A. Hypervalent Iodine in Organic Synthesis , Academic Press : London , 1997 ; (b) Skulski, L.; Organic iodine (I, II, V) chemistry: 10 years of developments at the medical university of Warsaw, Poland. Molecules 2000, 5, 1331; (c) Zhdankin, V.V.; Stang, P.J. Developments in the Chemistry of Polyvalent Iodine Compounds. Chem. Rev. 2002, 102, 2523; (d) Zhdankin, V. V. Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A. Ed., Johnz Wiley & Sons, Ltd.: Chichester, England, 2004.
  • Zanka , A. ; Takeuchi , H. ; Kubota , A. Large-scale preparation of iodobenzene dichloride and efficient monochlorination of 4-aminoacetophenone . Org. Process Res. Devel. 1998 , 2 , 270 – 273 .
  • Prakash , O. ; Batra , A. ; Sharma , V. ; Saini , R. K. ; Verma , R. S. Hypervalent iodine(III) mediated synthesis of 2-substituted benzoxazoles . J. Ind. Chem. Soc. 2003 , 80 , 1031 – 1033 .
  • Prakash , O. ; Sharma , P. K. ; Saini , N. Hypervalent iodine reagents in the synthesis of heterocyclic compounds . Synlett 1994 , 221 – 227 .
  • Prakash , O. ; Batra , H. ; Kaur , H. ; Sharma , P. K. ; Sharma , V. ; Singh , S. P. ; Moriarty , R. M. Hypervalent iodine oxidative rearrangement of anthranilamides, salicylamides, and some p-substituted amides: A new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones, and related compounds . Synthesis 2001 , 541 .
  • Sadana , A. ; Mirza , Y. ; Aneja , K. R. ; Prakash , O. Hypervalent iodine–mediated synthesis of 1-aryl/hetryl-1,2,4-triazolo[4,3-a] pyridines and 1-aryl/hetryl 5-methyl-1,2,4-triazolo[4,3-a]quinolines as antibacterial agents. Eur. J. Med. Chem. 2003, 38, 533–536.
  • Prakash , O. ; Bhardwaj , V. ; Kumar , R. ; Tayagi , P. ; Aneja , K. R. Organoiodine(III)–mediated synthesis of 3-aryl/hetryl-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidines as antibacterial agents . Eur. J. Med. Chem. 2004 , 39 , 1073 – 1077 .
  • Prakash , O. ; Kumar , R. ; Sharma , D. ; Naithani , R. ; Kumar , R. Organoiodine(III)-mediated efficient synthesis of new 3,9-diaryl-bis-1,2,4-triazolo[4,3-a][4,3-c]pyrimidines . Heteroatom Chem. 2006 , 17 , 653 – 655 .
  • Prakash , O. ; Kumar , A. ; Sadana , A. K. ; Singh , S. P. A novel synthesis of new 3-aryl-7-methylpyrano[4,3-b]pyran-4h,5h-diones using hypervalent iodine(III) reagents . Synthesis 2006 , 0021 .
  • The studies dealing with the biological activities of 2-aryl-6-chloro-2,3-dihydro-4(1H)-quinolones (3) are under way and will be published elsewhere.
  • (a) Donnely , J. A. ; Farrel , D. F. The chemistry of 2′-amino analogs of 2′-hydroxychalcone and its derivatives . J. Org. Chem , 1990 , 55 , 1757 . (b) Chalcone derivatives as precursors of 1,2,3,4-tetrahydro-4-quinolones. Tetrahedron 1990, 46, 885.
  • 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 .
  • Tokes , A. L. ; Forro , I. Bromo-derivatives of 2′-NHR-3,4-methylenedioxychalcone and its 4-quinolone isomer . Synth. Commun. 1991 , 21 , 1201 .

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