Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(17): 2849-2854
DOI: 10.1055/s-2006-942522
DOI: 10.1055/s-2006-942522
PAPER
© Georg Thieme Verlag Stuttgart · New York
Ionic Liquid Promoted Facile One-Pot Synthesis of 1-Pyridylimidazo[1,5-a]pyridines from Dipyridylketone and Aryl Aldehydes
Further Information
Received
6 February 2006
Publication Date:
25 July 2006 (online)
Publication History
Publication Date:
25 July 2006 (online)
Abstract
A highly efficient one-pot methodology has been developed to synthesize a class of substituted 1-pyridylimidazo[1,5-a]pyridines, using Bronsted acidic ionic liquid 1-butylimidazolium tetrafluoroborate, [Hbim]BF4 in excellent isolated yields in the absence of any catalyst. The methodology is characterized by simple work-up procedures along with efficient recovery and recycling of the ionic liquid, which acts as a reaction medium as well as a promoter.
Key words
imidazo[1,5-a]pyridines - aldehyde - heterocycles - ionic liquids - ammonium acetate
- 1
Biachi G.Rodriguez A.Yakurshigiu K. J. Org. Chem. 1989, 54: 4497 - 2
Bolger L.Brittain RJ.Jack D.Jackson MR.Martin LE.Mills J.Poynter D.Tyers MB. Nature (London) 1972, 238: 354 - 3
Zito SW.Martlnez M. J. Biol. Chem. 1980, 255: 8645 - 4
Jansonius JN.Eichele G.Ford GC.Picot D.Thaller C.Vicent MG. In TransaminasesChristen P.Metzler DE. Wiley; New York: 1985. p.110 - 5
Arbilla S.Allen J.Wick A.Langer S. Eur. J. Pharmacol. 1986, 130: 257 - 6
Ford NF.Browne LJ.Campbell T.Gemenden C.Goldstein R.Gude C.Wasley JNF. J. Med. Chem. 1985, 28: 164 - 7
Ligtenbarg AJ.Spek AL.Hage R.Feringa BL. J. Chem. Soc., Dalton Trans. 1999, 659 - 8
Bluhm ME.Ciesielski M.Gorls H.Walter O.Doring M. Inorg. Chem. 2003, 42: 8878 -
9a
Bower JD.Ramage GR. J. Chem. Soc. 1955, 2834 -
9b
Winterfeld K.Franzke H. Angew. Chem., Int. Ed. Engl. 1963, 75: 1101 -
10a
Bourdais J.Omar A.-ME. J. Heterocycl. Chem. 1980, 17: 555 -
10b
El Khadem HS.Kawai J.Swartz DL. Heterocycles 1989, 28: 239 - 11
Sasaki K.Tsurumori A.Hirota T. J. Chem. Soc., Perkin Trans. 1 1998, 3851 - 12
Palacios F.Alonso C.Rubiales G. Tetrahedron 1995, 51: 3683 - 13
Katritzky AR.Qiu G. J. Org. Chem. 2001, 66: 2862 -
14a
Krapcho AP.Powell JR. Tetrahedron Lett. 1986, 27: 3713 -
14b
Grigg R.Kennewell P.Savic V.Sridharan V. Tetrahedron 1992, 48: 10423 - 15
Wang J.Dyers L.Mason R.Amoyaw P.Bu XR. J. Org. Chem. 2005, 70: 2353 - 16
Bluhm ME.Ciesielski M.Gorls H.Walter O.Doring M. Angew. Chem. Int. Ed. 2002, 41: 2962 -
17a
Welton T. Chem. Rev. 1999, 99: 2071 -
17b
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 -
18a
Deshmukh RR.Rajagopal R.Srinivasan KV. Chem. Commun. 2001, 1544 -
18b
Rajagopal R.Jarikote DV.Srinivasan KV. Chem. Commun. 2002, 616 -
19a
Palimkar SS.Siddiqui SA.Thomas D.Lahoti RJ.Srinivasan KV. J. Org. Chem. 2003, 68: 9371 -
19b
Siddiqui SA. Synlett 2006, 155 - 20
Perrin DD. Ionization Constant of Inorganic Acids and Bases in Aqueous Solution 2nd ed.: Pergamon; Elmsford, New York: 1982. - 21
Fletcher KA.Storey IA.Hendricks AE.Pandey S.Pandey S. Green Chem. 2001, 3: 210