RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2011(3): 459-462
DOI: 10.1055/s-0030-1258393
DOI: 10.1055/s-0030-1258393
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with Hexamethyldisilazane in Molten Tetrabutylammonium Bromide
Weitere Informationen
Received
15 November 2010
Publikationsdatum:
11. Januar 2011 (online)
Publikationsverlauf
Publikationsdatum:
11. Januar 2011 (online)

Abstract
A simple and efficient method for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in molten tetrabutylammonium bromide as an inexpensive and non toxic solvent has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, the use of an ionic liquid as a green solvent, and the availability of reagents.
Key words
2,4,5-triaryl-1H-imidazole - hexamethyldisilazane - ionic liquids - aldehydes
- 1
Brimblecombe RW.Duncan WAM.Durant GJ.Emmett JC.Ganellin CR.Parons ME. J. Int. Med. Res. 1975, 3: 86 - 2
Lee JC.Laydon JT.McDonnell PC.Gallagher TF.Kumar S.Green D.McNulty D.Blumenthal MJ.Heys JR.Landvatter SW.Strickler JE.McLaughlin MM.Siemens IR.Fisher SM.Livi GP.White JR.Adams JL.Young PR. Nature 1994, 372: 739 - 3
Maier T,Schmierer R,Bauer K,Bieringer H,Buerstell H, andSachse B. inventors; US 4,820,335. ; Chem. Abstr. 1989, 111, 19494 - 4
Schmierer R,Mildenberger H, andBuerstell H. inventors; DE 3614364. ; Chem. Abstr. 1988, 108, 37838 - 5
Heeres J.Backx LJJ.Mostmans JH.Van Custem J. J. Med. Chem. 1979, 22: 1003 - 6
Abrahams SL.Hazen RJ.Batson AG.Phillips AP. J. Pharmacol. Exp. Ther. 1989, 249: 359 - 7
Radziszewski B. Chem. Ber. 1882, 15: 1493 - 8
Japp FR.Robinson HH. Chem. Ber. 1882, 15: 1268 - 9
Grimmett MR. In Comprehensive Heterocyclic Chemistry II Vol. 3:Katritzky AR.Rees CW.Scriven EFV. Pergamon; Oxford: 1996. p.77 - 10
Balalaie S.Arabanian A.Hashtroudi MS. Monatsh. Chem. 2000, 131: 945 - 11
Sharma GVM.Jyothi Y.Lakshmi PS. Synth. Commun. 2006, 36: 2991 - 12
Heravi MM.Bakhtiari K.Oskooie HA.Taheri S.
J. Mol. Catal. A: Chem. 2007, 263: 279 - 13
Kidwai M.Mothsra P.Bansal V.Goyal R. Monatsh. Chem. 2006, 137: 1189 - 14
Sangshetti JN.Kokare ND.Kothakar SA.Shinde DB. Monatsh. Chem. 2008, 139: 125 - 15
Usyatinsky AY.Khmelnitsky YL. Tetrahedron Lett. 2000, 41: 5031 - 16
Wolkenberg SE.Winoski DD.Leister WH.Wang Y.Zhoa Z.Lindsley CW. Org. Lett. 2004, 6: 1453 - 17
Kidwai M.Saxena S.Rastogi S. Bull. Korean Chem. Soc. 2005, 26: 2051 - 18
Wang LM.Wang YH.Tian H.Yao YF.Shao JH.Liu B. J. Fluorine Chem. 2006, 127: 1570 -
19a
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 -
19b
Khodaei MM.Khosropour AR.Kookhazadeh M. Can. J. Chem. 2005, 83: 209 -
20a
Welton T. Chem. Rev. 1999, 99: 2071 -
20b
Rajagopal R.Jarikote DV.Srinivasan KV. Chem. Commun. 2002, 616 -
21a
Khosropour AR.Khodaei MM.Beygzadeh M.Jokar M. Heterocycles 2005, 65: 767 -
21b
Khodaei MM.Khosropour AR.Jowkar M. Synthesis 2005, 1301 - 22
Shelke KF.Sapkal SB.Sonar SS.Madje BR.Shingate BB.Shingare MS. Bull. Korean Chem. Soc. 2009, 30: 5