Hypervalent Iodine in Synthesis 81: A One-Pot Procedure for the Synthesis of 1H-Imidazole Derivatives by Cyclocondensation of Ketones with [Hydroxy(tosyloxy)iodo]benzene and Amidines

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

-Tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB), followed by treatment with amidines provides a one-pot procedure for the synthesis of 1H-imidazole derivatives with good yields.

References

• 1 Grimmet MR. Comprehensive Organic Chemistry   Vol. 4:  Barton D. Ollis WB. Pergammon Press; New York: 1979. 
  Google Scholar
• 2 Fox SW. Chem. Rev.  1943,  32:  47 
  CrossrefGoogle Scholar
• 3 Townsend LB. Chem. Rev.  1967,  67:  533 
  CrossrefGoogle Scholar
• 4a Vorlaufige M. Chem. Ber.  1901,  34:  637 
  Google Scholar
• 4b Burtles R. Pyman FL. J. Chem. Soc.  1923,  123:  361 
  Google Scholar
• 4c Weidenhagen R. Herrmann R. Chem. Ber.  1935,  68:  1953 
  Google Scholar
• 4d Bredereck H. Theilig G. Chem. Ber.  1953,  86:  88 
  Google Scholar
• 4e Novelli A. Santis AD. Tetrahedron Lett.  1967,  265 
  Google Scholar
• 4f Kornis RM. Nyitrai J. Lempert K. Chem. Ber.  1971,  104:  3080 
  Google Scholar
• 4g Scheinbaum ML. Dines MB. Tetrahedron Lett.  1971,  2205 
  Google Scholar
• 4h Nakanishi S. Nantaku J. Otsuji Y. Chem. Lett.  1983,  341 
  Google Scholar
• 4i Inoue M. Matsumoto K. Ohta A. J. Heterocycl. Chem.  1983,  20:  1277 
  Google Scholar
• 4j Singh B. Heterocycles  1992,  34:  2373 
  Google Scholar
• 5a Stang PJ. Surber BW. Chen ZC. Roberts KA. Anderson AG. J. Am. Chem. Soc.  1987,  109:  228 
  CrossrefGoogle Scholar
• 5b Chen ZC. Jin YY. Stang PJ. J. Org. Chem.  1987,  52:  4117 
  CrossrefGoogle Scholar
• 5c Chen ZC. Stang PJ. Jin YY. J. Org. Chem.  1987,  52:  4115 
  CrossrefGoogle Scholar
• 5d Yan J. Zhong LR. Chen ZC. J. Org. Chem.  1991,  56:  459 
  CrossrefGoogle Scholar
• 5e Liu ZD. Chen ZC. J. Org. Chem.  1993,  58:  1924 
  CrossrefGoogle Scholar
• 5f Chen DW. Chen ZC. Tetrahedron Lett.  1994,  35:  7637 
  CrossrefGoogle Scholar
• 5g Yan J. Chen ZC. Tetrahedron Lett.  1999,  40:  5757 
  CrossrefGoogle Scholar
• 6 Zhang PF. Chen ZC. Synthesis  2000,  1219 
  Article in Thieme ConnectGoogle Scholar
• 7 Kempter G. Spindler J. Fiebig HJ. Sarodnick G. J. Prakt. Chem.  1971,  313:  977 
  CrossrefGoogle Scholar