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Synthesis 2011(16): 2644-2650
DOI: 10.1055/s-0030-1260099
DOI: 10.1055/s-0030-1260099
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Facile Synthesis of Pyrimidine-Isoxazoline Hybrids in a [bmim][PF6]-Water Biphasic System
Further Information
Received
25 March 2011
Publication Date:
27 July 2011 (online)
Publication History
Publication Date:
27 July 2011 (online)
Abstract
The convenient synthesis of a library of pyrimidine-isoxazoline hybrids in 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6])-water/potassium hydroxide at ambient temperature has been accomplished. The ionic liquid [bmim][PF6], immiscible in water, can be easily recycled for reuse after separation of the products without any noticeable diminution in its activity. The protocol is rapid, the yields are good to excellent, and the method is facile.
Key words
pyrimidines - dihydroisoxazoles - ionic liquids - water - biphasic systems
- Supporting Information for this article is available online:
- Supporting Information
- 1
Gaonkar SL.Lokanatha Rai KM.Prabhuswamy B. Med. Chem. Res. 2007, 15: 407 -
2a
Zificsak CA.Hlasta DJ. Tetrahedron 2004, 60: 8991 -
2b
Haino T.Tanaka M.Ikeda K.Kubo K.Mori A.Fukazawa Y. Tetrahedron Lett. 2004, 45: 2277 -
3a
Kromann H.Slok FA.Stensbol TB.Brauner-Osborne H.Madsen U.Krogsgaard-Larsen P. J. Med. Chem. 2002, 45: 988 -
3b
Conti P.De Amici M.Roda G.Vistoli G.Stensbol TB.Brauner-Osborne H.Madsen U.Toma L.De Micheli C. Tetrahedron 2003, 59: 1443 - 4
Hansen TV.Wu P.Fokin VV. J. Org. Chem. 2005, 70: 7761 - 5
Waldo JP.Larock RC. Org. Lett. 2005, 7: 5203 - 6
Vicentini CB.Verones AC.Poli T.Guameri M.Gioni P.Ferreti V. J. Heterocycl. Chem. 1990, 27: 1481 - 7
Higashida S.Nakashima H.Tohda Y.Tani K.Nishiwaki N.Ariga M. Heterocycles 1992, 34: 1511 - 8
Mizuno K.Ichinose N.Tamai T.Otsuja Y. J. Org. Chem. 1992, 57: 4669 - 9
Shankar BB.Yang DY.Girton S.Ganguly AK. Tetrahedron Lett. 1998, 39: 2447 - 10
Bhosale S.Kurhade S.Prasad UV.Palle VP.Bhuniya D. Tetrahedron Lett. 2009, 50: 3948 - 11
Martins MAP.Pereira CMP.Cunico W.Moura S.Rosa FA.Peres RL.Machado P.Zanatta N.Bonacorso HG. Ultrason. Sonochem. 2006, 13: 364 - 12
Chowdhury P.Das AM.Goswami P. Steroids 2005, 70: 494 - 13
Norman AL.Shurrush KA.Calleroz AT.Mosher MD. Tetrahedron Lett. 2007, 48: 6849 -
14a
Eibler E.Kasbauer J.Pohl H.Sauer J. Tetrahedron Lett. 1987, 28: 1097 -
14b
Corbett DF. J. Chem. Soc., Perkin Trans. 1 1986, 421 - 15
Armstrong SK.Collington EW.Knight JG.Naylorb A.Warren S. J. Chem. Soc., Perkin Trans. 1 1993, 1433 -
16a
Liu KC.Shelton BR.Howe RK. J. Org. Chem. 1980, 45: 3916 -
16b
Gi HJ.Xiang Y.Schinazi RF.Zhao K. J. Org. Chem. 1997, 62: 88 - 17
Lee GA. Synthesis 1982, 508 - 18
Ye Y.Zheng Y.Xu GY.Liu LZ. Heteroat. Chem. 2003, 14: 254 - 19
Hassner A.Lokanatha Rai KM. Synthesis 1989, 57 - 20
Kim J.Ryu E. Synth. Commun. 1990, 20: 1373 - 21
Kanemasa S.Matsuda H.Kamimurac A.Kakinamid T. Tetrahedron 2000, 56: 1057 - 22
Kumar V.Kaushik MP. Tetrahedron Lett. 2006, 47: 1457 - 23
Seregin IV.Ovchinnikov IV.Makhova NN.Lyubetsky DV.Lyssenko KA. Mendeleev Commun. 2003, 13: 230 - 24
Armstrong W.He L.Liu YS. Anal. Chem. 1999, 71: 3873 - 25
Suarez PA.Dullius JEL.Einloft S.DeSouza RF.Dupont J. Polyhedron 1996, 15: 1217 - 26
Manthiriyappan S.Lee CK. J. Mol. Catal. B: Enzym. 2009, 60: 1