Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 17
328
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Highly Efficient One-Pot Synthesis of 2-Aminobenzoxazoles Using Triflic Acid as a Cyclodesulfurizing Reagent

, , &
Pages 2631-2639 | Received 20 Apr 2010, Published online: 29 Jun 2011

REFERENCES

  • (a) Brittain , D. R. ; Johnstone , C. ; Davies , G. M. ; Large , M. S. Heterocyclic derivatives and their use as integrin inhibitor. World Patent 2000005224, 2000; (b) Harris , N. V. ; Fenton , G. Substituted tetrahydroisoquinolines for use in the treatment of inflammatory diseases. World Patent 2002098426, 2002; (c) Surleraux , D. L. N. G. ; Vendeville , S. M. H. ; Verschueren , W. G. ; De Bethune , M.-P. T. M. M. G. ; De Kock , H. A. ; Tahri , A. Broad spectrum 2-amino-benzoxazole sulphonamide HIV protease inhibitors. World Patent 2002092595, 2002 .
  • (a) Haviv , F. ; Ratajczyk , J. D. ; DeNet , R. W. ; Kerdesky , F. A. ; Walters , R. L. ; Schmidt , S. P. ; Holms , J. H. ; Young , P. R. ; Carter , G. W. 3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: Inhibitors of immune complex induced inflammation . J. Med. Chem. 1988 , 31 , 1719 – 1728 ; (b) Lok , R. ; Leone , R. E. ; Williams , A. J. Facile rearrangements of alkynylamino heterocycles with noble metal cations . J. Org. Chem. 1996 , 61 , 3289 – 3297 .
  • Ozaki , S. Recent advances in isocyanate chemistry . Chem. Rev. 1972 , 72 , 457 – 496 .
  • Ogura , H. ; Mineo , S. ; Nakagawa , K. Studies on heterocyclic compounds, XXXIV. Synthesis of 2-substituted aminobenzoxazoles with nickel peroxide . Chem. Pharm. Bull. 1981 , 29 , 1518 – 1524 .
  • (a) Janssens , F. E. ; Van Offenwert , T. T. ; Stokbroekx , R. A. ; Boar , B. R. Substituted N-[(4-piperidinyl)alkyl] bicyclic condensed ozazol- and thiazolamines. Eur. Patent Appl. EP 0199400, 1986; (b) Stokbroekx , R. A. ; Luyckx , M. G. M. ; Janssens , F. E. Benzoxazol- and benzothiazolamine derivatives. Eur. Patent Appl. EP 184257, 1986; (c) Qian , X.-H. ; Li , Z.-B. ; Song , G.-H. ; Li , Z. Yellow HgO as an efficient cyclodesulfurizing agent in the synthesis of 2-substituted aminobenzoxazoles from N-(2-hydroxyphenyl)-N′-phenylthioureas . J. Chem. Res., Synop. 2001 , 4 , 138 – 139 .
  • (a) Simov , D. ; Davidkov , K. Synthesis of 2-aminobenzoxazoles and 2-iminobenzoxazolines . Chem. Heterocycl. Comp. 1976 , 12 , 151 – 152 ; (b) Simov , D. ; Davidkov , K. Synthesis and IR spectra of some 2-aminobenzoxazole derivatives . Chem. Heterocycl. Comp. 1981 , 17 , 437 – 440 .
  • (a) Chang , H.-S. ; Yon , G.-H. ; Kim , Y.-H. Facile synthesis of 2-substituted aminobenzoxazole: One-pot cyclodesulfurization of N-(2-hydroxyphenyl)-N′-phenylthioureas with superoxide radical anion . Chem. Lett. 1986 , 1291 – 1294 .
  • Wishart , N. ; Rudolph , A. ; Ritter , K. Transition metal–mediated process. U.S. Patent Appl. 20030109714, 2003 .
  • Omar , A. ; Mohsen , M. E. ; Habib , N. S. ; Aboulwafa , O. M. The cyclodesulfurization of thio compounds, XVI: Dicyclohexylcarbodiimide as an efficient cyclodesulfurizing agent in the synthesis of heterocyclic compounds from various thio compounds . Synthesis 1977 , 864 – 865 .
  • Kim , H. T. ; Lee , N. ; Lee , G-J. ; Kim , J. N. A mild cyclodesulfurization of N-(2-hydroxyethyl)-N′-phenylthioureas to 2-phenylamino-2-oxazolines using TsCl/NaOH . Tetrahedron 2001 , 57 , 7137 – 7141 .
  • Tian , Z. ; Plata , D. J. ; Wittenberger , S. J. ; Bhatia , A. V. A general synthesis of N-aryl- and N-alkyl-2-aminobenzoxazoles. Tetrahedron Lett. 2005, 46, 8341–8343.
  • (a) Howells , R. D. ; McCown , J. D. Trifluoromethanesulfonic acid and derivatives . Chem. Rev. 1977 , 77 , 69 – 92 ; (b) Stang , P. J. ; White , M. R. Trifilic acid and its derivatives . Aldrichim. Acta 1983 , 16 , 15 – 22 ; (c) Stang , P. J. ; White , M. R. In Encyclopedia of Reagents for Organic Synthesis. L. A. Paquette (Ed.); Wiley: Chichester, 1995; pp. 5143–5146 .
  • (a) Kirihara , M. ; Yokoyama , S. ; Momose , T. A significant effect of triflic acid on the hypervalent λ n-iodane-mediated fragmentation of the tertiary cyclopropanol system . Synth. Commun. 1998 , 28 , 1947 – 1956 ; (b) Zhang , H.-B. ; Liu , L. ; Liu , Y.-L. ; Chen , Y.-J. ; Wang , J. ; Wang , D. Triflic acid–catalyzed Michael reactions of indole and pyrrole compounds with α,β-unsaturated ketones in water . Synth. Commun. 2007 , 37 , 173 – 181 ; (c) Coulombel , L. ; Duñach , E. Cycloisomerization of olefinic carboxylic acids catalyzed by trifluoromethanesulfonic acid . Synth. Commun. 2005 , 35 , 153 – 160 .
  • (a) Victor , J. C. ; Nicholas , S. D. A one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles . Tetrahedron Lett. 2006 , 47 , 3747 – 3750 ; (b) Villemin , D. ; Bar , N. ; Hammadi , M. Triflic acid an efficient catalyst for the Thiele–Winter reaction . Tetrahedron Lett. 1997 , 38 , 4777 – 4778 .
  • Khatik , G. L. ; Pal , A. ; Apsunde , T. D. ; Nair , V. A. A highly efficient methodology for 5-methyl-3-aryl-2-thiooxazolidin-4-ones using lithium perchlorate in DIPEA mediated synthesis . J. Heterocycl. Chem. 2010 , 47 , 734 – 739 .
  • (a) Shimizu , K. Solubilization and desulfurization of high sulfur coal under mild conditions with trifluoromethanesulfonic acid . Fuel Energy Abstr. 1996 , 37 , 335 ; (b) Shimizu , K. ; Iwami , Y. ; Suganuma , A. ; Saito , I. Behaviour of sulfur in high-sulfur coal in a superacidic medium without gaseous hydrogen . Fuel 1997 , 76 , 939 – 943 .

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.