Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 6
108
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of N‐Aryl‐2‐substituted Tetrahydrobenzimidazoles via Direct N‐Arylation

, &
Pages 1001-1009 | Received 06 Apr 2006, Published online: 24 Feb 2007

References

  • Dannhardt , G. and Kiefer , W. 2001 . Cyclooxygenase inhibitors—Current status and future prospects . Eur. J. Med. Chem. , 36 ( 2 ) : 109 – 126 .
  • Friesen , R. W. , Brideau , C. , Chan , C.‐C. , Charleson , S. , Deschenes , D. , Dube , D. , Ethier , D. , Fortin , R. , Gauthier , J. Y. , Girard , Y. , Gordon , R. , Greig , G. , Riendeau , D. , Savoie , C. , Wang , Z. , Wong , E. , Visco , D. , Xu , L. J. and Young , R. N. 1998 . 2‐Pyridinyl‐3‐(4‐methylsulfonyl)phenylpyridines: Selective and orally active cyclooxygenase‐2 inhibitors . Bioorg. Med. Chem. Lett. , 8 : 2777 – 2782 .
  • Penning , T. D. , Tally , J. J. , Bertenshaw , S. R. , Carter , J. S. , Collins , P. W. , Doctor , S. , Graneto , M. J. , Lee , L. F. , Malecha , J. W. , Miyashiro , J. M. , Rogers , R. S. , Rogier , D. J. , Yu , S. S. , Anderson , G. D. , Burton , E. G. , Cogburn , J. N. , Gregory , S. A. , Koboldt , C. M. , Perkins , W. E. , Seibert , K. , Veenhuizen , A. W. , Zhang , Y. Y. and Isakson , P. C. 1997 . Synthesis and biological evaluation of the 1,5‐diarylpyrazole class of cyclooxygenase‐2 inhibitors: Identification of 4‐[5‐(4‐methylphenyl)‐3‐(trifluoromethyl)‐1H‐pyrazol‐1‐yl]benzenesulfonamide (SC‐58635, celecoxib) . J. Med. Chem. , 40 ( 9 ) : 1347 – 1365 .
  • Talley , J. J. , Brown , D. L. , Carter , J. S. , Graneto , M. J. , Koboldt , C. M. , Masferrer , J. L. , Perkins , W. E. , Rogers , R. S. , Shaffer , A. F. , Zhang , Y. Y. , Zweifel , B. S. and Seibert , K. 2000 . 4‐[5‐Methyl‐3‐phenylisoxazol‐4‐yl]‐benzenesulfonamide, valdecoxib: A potent and selective inhibitor of COX‐2 . J. Med. Chem. , 43 ( 5 ) : 775 – 777 .
  • Khanna , I. K. , Weier , R. M. , Yu , Y. , Xu , X. , Koszyk , F. J. , Collins , P. W. , Koboldt , C. M. , Veenhuizen , A. W. , Perkins , W. E. , Casler , J. J. , Masferrer , J. L. , Zhang , Y. Y. , Gergory , S. A. , Seibert , K. and Isakkson , P. 1997 . 1,2‐Diarylimidazole as potent and cyclooxygenase‐2 selective inhibitors, and orally active anti‐inflammatory agents . J. Med. Chem. , 40 : 1634 – 1647 .
  • Lunn , W. H. W. , William , H. W. , Monn , J. A. and Zimmerman , D. M. US Patent, 1999, 5,552,426 .
  • Wasserman , H. H. , Wolff , M. S. , Ktiller , H. , Aaito , I. and Pickett , J. E. 1981 . The dye‐sensitized photooxidation of imidazoles . Tetrahedron , 37 suppl. 1 : 191 – 200 .
  • Khan , M. A. and Polya , J. B. 1970 . Syntheses of heterocyclic compounds, part II: N‐arylimidazoles by Ullmann condensation . J. Chem. Soc. , : 85 – 90 .
  • Katritzky , A. R. and Rees , C. W. 1984 . Comprehensive Heterocyclic Chemistry Vol. 5 , 390 Oxford : Pergamon Press .
  • Begtrup , M. 1979 . Reactions of 4‐halogeno‐ and 4‐methylthio‐imidazolium salts with sulphide and methanethiolate ions . J. Chem. Soc. Perkin Trans. , : 521 – 527 .
  • Smith , W. J. III and Sawyer , J. S. 1996 . A novel and selective method for the N‐arylation of indoles mediated by KF/Al2O3 . Tetrahedron Lett. , 37 ( 3 ) : 299 – 302 .
  • Hashimoto , H. , Imamura , K. , Haruta , J. and Wakitani , K. 2002 . 4‐(4‐Cycloalkyl/aryl‐oxazol‐5‐yl)benzenesulfonamides as selective cyclooxygenase‐2 inhibitors: Enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX‐2 inhibitor JTE‐522(1) . J. Med. Chem. , 45 ( 7 ) : 1511 – 1517 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.