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Synthesis 2006(22): 3849-3854
DOI: 10.1055/s-2006-950306
DOI: 10.1055/s-2006-950306
PAPER
© Georg Thieme Verlag Stuttgart · New York
Solvent-Free Synthesis of γ-Nitroketones and γ-Nitroesters Promoted by the Ionic Liquid/K2CO3 Catalytic System
Weitere Informationen
Received
22 June 2006
Publikationsdatum:
09. Oktober 2006 (online)
Publikationsverlauf
Publikationsdatum:
09. Oktober 2006 (online)
Abstract
A convenient solvent-free synthesis of γ-nitroketones and γ-nitroesters based on the reaction of nitroalkanes with α,β-unsaturated carbonyl compounds in the ultrasonically activated heterogeneous catalytic system 1-butyl-3-methylimidazolium tetra-fluoroborate ([bmim][BF4])/K2CO3 has been developed. The system retained its catalytic activity over three reaction cycles.
Key words
Michael additions - ionic liquids - catalysis - esters - ketones
- 1
Perlmutter P. Conjugate Addition Reactions in Organic Synthesis Pergamon; Oxford: 1992. - 2
Ballini R.Bosica G.Fiorini D.Palmieri A.Petrini M. Chem. Rev. 2005, 105: 933 - 3
Mdoe JEG.Clark JH.Macquarrie DJ. Synlett 1998, 625 -
4a
Ballini R.Bosica G. Tetrahedron Lett. 1996, 37: 8027 -
4b
Boruah A.Baruah M.Prajapati D.Sandh JS. Chem. Lett. 1996, 965 -
4c
Ranu BC.Bhar S. Tetrahedron 1992, 48: 1327 - 5
Jouglet B.Blanco L.Rousseau G. Synlett 1991, 907 -
6a
Welton T. Chem. Rev. 1999, 99: 2071 -
6b
Wasserscheid P.Welton T. Ionic Liquids in Synthesis Willey-VCH; New York: 2003. -
7a
Kryshtal GV.Zhdankina GM.Astakhova IV.Zlotin SG. Russ. Chem. Bull. 2004, 53: 647 -
7b
Fan X.Hu X.Zhang X.Wang J. Aust. J. Chem. 2004, 57: 1067 -
7c
Kotrusz P.Toma S.Schmalz H.-G.Adler A. Eur. J. Org. Chem. 2004, 1577 -
7d
Yadav JS.Reddy BVS.Baishya G.Narsaiah AV. Chem. Lett. 2005, 102 -
7e
Ranu BC.Banerjee S. Org. Lett. 2005, 7: 3049 -
7f
Gallo V.Giardina-Papa D.Mastrorilli P.Nobile CF.Suranna GP.Wang Y. J. Organomet. Chem. 2005, 690: 2215 -
8a
Kryshtal GV.Zhdankina GM.Zlotin SG. Eur. J. Org. Chem. 2005, 2822 -
8b
Zlotin SG.Kryshtal GV.Zhdankina GM.Belyakov PA.Serebryakov EP. Russ. Chem. Bull. 2004, 53: 659 - 9
Tsogoeva SB.Jagtap SB.Ardemasova ZA.Kalikhevich VN. Eur. J. Org. Chem. 2004, 4014 - 10
Davey W.Tivey DJ. J. Chem. Soc. 1958, 2276 -
11a
Ono N.Kamimuro A.Kaji A. Synthesis 1984, 226 -
11b
Sebti S.Boukhal H.Hanafi N.Boulaajaj S. Tetrahedron Lett. 1999, 40: 6207 -
12a
Prieto A.Halland N.Joergensen KA. Org. Lett. 2005, 7: 3897 -
12b
Smith LJ.Showell JS. J. Org. Chem. 1952, 17: 827 -
12c
Kozlov LM.Fink EF. Trudy Kazan. Khim. Tekhnol. Inst. im. S. M. Kirova 1954-1955, 19-20: 49 ; Chem. Abstr. 1957, 51, 11267h -
12d
Nazarski RB.Skowroñski R. J. Chem. Soc., Perkin Trans. 1 1989, 1603 -
13a
Clark JH.Cork DG.Gibls HW. J. Chem. Soc., Perkin Trans. 1 1983, 2253 -
13b
Bapat JB.Black DSC. Aust. J. Chem. 1968, 21: 2483 -
13c
Barton DHR.Motherwell WB.Simon ES.Zard SZ. J. Chem. Soc., Perkin Trans. 1 1986, 2243 -
13d
Tishchenko JG.Berezovskii VV. Vesti Acad. Navuk BSSR, Ser. Khim. Navuk. 1977, 83 ; Chem. Abstr. 1987, 88, 22077z -
13e
Kambe S.Yasuda H. Bull. Chem. Soc. Jpn. 1966, 39: 2549 -
13f
Isagulyants VS.Markosyan EL. J. Appl. Chem. USSR (Engl. Transl.) 1964, 1146 -
14a
Kryshtal GV.Zhdankina GM.Zlotin SG. Russ. Chem. Bull. (Engl. Transl.) 2004, 53: 652 -
14b
Serebryakov EP.Nigmatov AG. Pharm. Chem. J. (Engl. Transl.) 1990, 24: 104 - 15
Ballini R.Bosica G.Fluorini D. Tetrahedron Lett. 2001, 42: 8471 - 16 For the use of organic salts with fluorinated anions as recoverable PTCs, see:
Kryshtal GV.Zhdankina GM.Zlotin SG. Eur. J. Org. Chem. 2005, 2822 -
17a
House HO.Respess WL.Whitesides GM. J. Org. Chem. 1966, 31: 3128 -
17b
Naves JR.Ardizio P. Bull. Soc. Chim. Fr. 1953, 494 -
17c
Russell A.Kenyon RL. Org. Synth., Coll. Vol. III Wiley; New York: 1955. p.747 - 18
Suarez PAZ.Dullius JIL.Finloft S.De Souza RF.Dupont J. Polyhedron 1996, 15: 1217