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Volumn 41, Issue 20, 2011, Pages 3060-3065

Condensation reactions of aromatic aldehydes with active methylene compounds catalyzed by alkaline ionic liquid

Author keywords

Active methylene compounds; alkaline ionic liquid; aromatic aldehydes; Knoevenagel condensation reaction

Indexed keywords

ALDEHYDE; CARBENE; IONIC LIQUID;

EID: 79960623984     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.517361     Document Type: Article
Times cited : (12)

References (33)
  • 1
    • 33947475960 scopus 로고
    • Reactions catalyzed by potassium fluoride III: The Knoevenagel reaction
    • Rand, L.; Swisher, J. V.; Cronin, C. J. Reactions catalyzed by potassium fluoride, III: The Knoevenagel reaction. J. Org. Chem. 1962, 27(10), 3505-3507.
    • (1962) J. Org. Chem. , vol.27 , Issue.10 , pp. 3505-3507
    • Rand, L.1    Swisher, J.V.2    Cronin, C.J.3
  • 2
    • 0001294942 scopus 로고
    • Substituted quinodimethans, I: Preparation and chemistry of 7 7 8,8-tetracyanoquinodimethan
    • Acker, D. S.; Hertler, W. R. Substituted quinodimethans, I: Preparation and chemistry of 7,7,8,8-tetracyanoquinodimethan. J. Am. Chem. Soc. 1962, 84(17), 3370-3374.
    • (1962) J. Am. Chem. Soc. , vol.84 , Issue.17 , pp. 3370-3374
    • Acker, D.S.1    Hertler, W.R.2
  • 3
    • 0026440620 scopus 로고
    • Acid-base catalysts derived from weakly acidic ion exchange resin: Efficiency in the Knoevenagel condensation
    • Saito, T.; Goto, H.; Honda, K.; Fujii, T. Acid-base catalysts derived from weakly acidic ion exchange resin: Efficiency in the Knoevenagel condensation. Tetrahedron Lett. 1992, 33(49), 7535-7538.
    • (1992) Tetrahedron Lett. , vol.33 , Issue.49 , pp. 7535-7538
    • Saito, T.1    Goto, H.2    Honda, K.3    Fujii, T.4
  • 4
    • 0001056276 scopus 로고
    • Ion-exchange resin catalysis of the Knoevenagel condensation of ketones
    • Richardhein, W.; Melvin, J. Ion-exchange resin catalysis of the Knoevenagel condensation of ketones. J. Org. Chem. 1961, 26(12), 4874-4878.
    • (1961) J. Org. Chem. , vol.26 , Issue.12 , pp. 4874-4878
    • Richardhein, W.1    Melvin, J.2
  • 5
    • 0010428097 scopus 로고    scopus 로고
    • The Knoevenagel condensation catalyzed by potassium fluoride
    • Dai, G. Y.; Shi, D. Q.; Zhou, L. H. The Knoevenagel condensation catalyzed by potassium fluoride. Huaxue Shiji 1996, 18(1), 39-40.
    • (1996) Huaxue Shiji , vol.18 , Issue.1 , pp. 39-40
    • Dai, G.Y.1    Shi, D.Q.2    Zhou, L.H.3
  • 6
    • 0036296302 scopus 로고    scopus 로고
    • Synthesis of ethyl a-cyanocinnamates catalyzed by KF-Al2O3 under ultrasound irradiation
    • Wang, S. X.; Li, J. T.; Yang, W. Z.; Li, T. S. Synthesis of ethyl a-cyanocinnamates catalyzed by KF-Al2O3 under ultrasound irradiation. Ultrasonics Sonochem. 2002, 9(3), 159-161.
    • (2002) Ultrasonics Sonochem. , vol.9 , Issue.3 , pp. 159-161
    • Wang, S.X.1    Li, J.T.2    Yang, W.Z.3    Li, T.S.4
  • 7
    • 33847330608 scopus 로고    scopus 로고
    • Layered silicate PLS-1: A new solid base catalyst for C-C bond forming reactions
    • DOI 10.1016/j.catcom.2006.08.015, PII S1566736706002858
    • Komura, K.; Kawamura, T.; Sugi, Y. Layered silicate PLS-1: A new solid base catalyst for C-C bond-forming reactions. Cat. Commun. 2007, 8(4), 644-648. (Pubitemid 46331001)
    • (2007) Catalysis Communications , vol.8 , Issue.4 , pp. 644-648
    • Komura, K.1    Kawamura, T.2    Sugi, Y.3
  • 8
    • 0343150934 scopus 로고    scopus 로고
    • Silica gel catalysed Knoevenagel condensation in dry media under microwave irradiation
    • DOI 10.1016/0040-4039(95)02318-6
    • De la Cruz, P.; Díez-Barra, E.; Loupy, A.; Langa, F. Silica gel-catalysed Knoevenagel condensation in dry media under microwave irradiation. Tetrahedron Lett. 1996, 37(7), 1113-1116. (Pubitemid 26052127)
    • (1996) Tetrahedron Letters , vol.37 , Issue.7 , pp. 1113-1116
    • De La Cruz, P.1    Diez-Barra, E.2    Loupy, A.3    Langa, F.4
  • 9
    • 24144493722 scopus 로고    scopus 로고
    • Niobium (V) chloride catalyzed Knoevenagel condensation: An efficient protocol for the preparation of electrophilic alkenes
    • DOI 10.1016/j.molcata.2005.06.026, PII S1381116905004231
    • Leelavathi, P.; Kumar, S. R. Niobium(V) chloride-catalyzed Knoevenagel condensation: An efficient protocol for the preparation of electrophilic alkenes. J. Mol. Cat. A: Chem. 2005, 240(1-2), 99-102. (Pubitemid 41231728)
    • (2005) Journal of Molecular Catalysis A: Chemical , vol.240 , Issue.1-2 , pp. 99-102
    • Leelavathi, P.1    Kumar, S.R.2
  • 10
    • 33750071701 scopus 로고    scopus 로고
    • A novel catalyst for the Knoevenagel condensation of aldehydes with malononitrile and ethyl cyanoacetate under solvent free conditions
    • DOI 10.1016/j.catcom.2006.03.008, PII S1566736706000768
    • Gawande, M. B.; Jayaram, R. V. A novel catalyst for the Knoevenagel condensation of aldehydes with malononitrile and ethyl cyanoacetate under solvent-free conditions. Catal. Commun. 2006, 7(12), 931-935. (Pubitemid 44585237)
    • (2006) Catalysis Communications , vol.7 , Issue.12 , pp. 931-935
    • Gawande, M.B.1    Jayaram, R.V.2
  • 11
    • 26044469928 scopus 로고    scopus 로고
    • 3 catalyzed Knoevenagel reaction of methylene compounds with aldehydes under solvent-free condition
    • Wang, L. M.; Sheng, J.; Zhang, L.; Han, J. W.; Fan, Z. Y.; Tian, H. Yb(OTf)3-catalyzed Knoevenagel reaction of methylene compounds with aldehydes under solvent-free condition. Chin. J. Org. Chem. 2005, 25(8), 964-968. (Pubitemid 41405095)
    • (2005) Chinese Journal of Organic Chemistry , vol.25 , Issue.8 , pp. 964-968
    • Wang, L.-M.1    Han, J.-W.2    Sheng, J.3    Fan, Z.-Y.4    Zhang, L.5    Tian, H.6
  • 13
    • 0034193712 scopus 로고    scopus 로고
    • Fluorapatite: New solid catalyst of the Knoevenagel reaction in heterogeneous media without solvent
    • Sebti, S.; Nazih, R.; Tahir, R.; Salhi, L.; Saber, A. Fluorapatite: New solid catalyst of the Knoevenagel reaction in heterogeneous media without solvent. Appl. Cat. A: Gen. 2000, 197(2), L187-L190.
    • (2000) Appl. Cat. A: Gen. , vol.197 , Issue.2
    • Sebti, S.1    Nazih, R.2    Tahir, R.3    Salhi, L.4    Saber, A.5
  • 14
    • 33750496468 scopus 로고    scopus 로고
    • Knoevenagel condensation over acidic zeolite
    • Zuo, B. J.; Wang, Q. L.; Wang, Y.; Ma, Y. D. Knoevenagel condensation over acidic zeolite. Chin. J. Cat. 2002, 23(6), 555-558.
    • (2002) Chin. J. Cat. , vol.23 , Issue.6 , pp. 555-558
    • Zuo, B.J.1    Wang, Q.L.2    Wang, Y.3    Ma, Y.D.4
  • 15
    • 34247264381 scopus 로고    scopus 로고
    • Knoevenagel condensation catalysed by poly(vinyl chloride)-supported tetraethylenepentamine (PVC-TEPA)
    • Dong, F.; Li, Y. Q.; Dai, R. F. Knoevenagel condensation catalysed by poly(vinyl chloride)-supported tetraethylenepentamine (PVC-TEPA). Chin. Chem. Lett. 2007, 18, 266-268.
    • (2007) Chin. Chem. Lett. , vol.18 , pp. 266-268
    • Dong, F.1    Li, Y.Q.2    Dai, R.F.3
  • 16
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids: Solvents for synthesis and catalysis
    • Welton, T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem. Rev. 1999, 99(8), 2071-2084.
    • (1999) Chem. Rev. , vol.99 , Issue.8 , pp. 2071-2084
    • Welton, T.1
  • 17
    • 12344296667 scopus 로고    scopus 로고
    • Chemical and biochemical transformations in ionic liquids
    • DOI 10.1016/j.tet.2004.10.070, PII S0040402004017867
    • Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Chemical and biochemical transformations in ionic liquids. Tetrahedron. 2005, 61, 1015-1060. (Pubitemid 40126710)
    • (2005) Tetrahedron , vol.61 , Issue.5 , pp. 1015-1060
    • Jain, N.1    Kumar, A.2    Chauhan, S.3    Chauhan, S.M.S.4
  • 18
    • 33846807717 scopus 로고    scopus 로고
    • Reactivity of ionic liquids
    • DOI 10.1016/j.tet.2006.11.001, PII S0040402006017480
    • Chowdhury, S.; Mohan, R. S.; Scott, J. L. Reactivity of ionic liquids. Tetrahedron. 2007, 63, 2363-2389. (Pubitemid 46204772)
    • (2007) Tetrahedron , vol.63 , Issue.11 , pp. 2363-2389
    • Chowdhury, S.1    Mohan, R.S.2    Scott, J.L.3
  • 19
    • 33847047785 scopus 로고    scopus 로고
    • A green and efficient synthesis of 9-aryl-3 4 5,6,7,9-hexahydroxanthene- 1,8-dione using task-specific ionic liquid as dual catalyst and solvent
    • Ma, J. J.; Zhou, X.; Zang, X. H.; Wang, C.; Wang, Z.; Li, J. C.; Li, Q. A green and efficient synthesis of 9-aryl-3,4,5,6,7,9-hexahydroxanthene-1,8-dione using task-specific ionic liquid as dual catalyst and solvent. Aus. J. Chem. 2007, 60, 146-148.
    • (2007) Aus. J. Chem. , vol.60 , pp. 146-148
    • Ma, J.J.1    Zhou, X.2    Zang, X.H.3    Wang, C.4    Wang, Z.5    Li, J.C.6    Li, Q.7
  • 20
    • 1642264118 scopus 로고    scopus 로고
    • Hydrotalcite catalysis in ionic liquid medium: A recyclable reaction system for heterogeneous Knoevenagel and nitroaldol condensation
    • DOI 10.1016/j.tetlet.2004.02.103, PII S0040403904004289
    • Khan, F. A.; Dash, J.; Satapathy, R.; Upadhyay, S. K. Hydrotalcite catalysis in ionic liquid medium: A recyclable reaction system for heterogeneous Knoevenagel and nitroaldol condensation. Tetrahedron Lett. 2004, 45(15), 3055-3058. (Pubitemid 38373728)
    • (2004) Tetrahedron Letters , vol.45 , Issue.15 , pp. 3055-3058
    • Khan, F.A.1    Dash, J.2    Satapathy, R.3    Upadhyay, S.K.4
  • 21
    • 1942471147 scopus 로고    scopus 로고
    • Room-temperature ionic liquids used as microwave absorbent to promote the Knoevenagel reaction
    • Xu, X. M.; Li, Y. Q.; Zhou, M. Y.; Tan, Y. H. Room-temperature ionic liquids used as microwave absorbent to promote the Knoevenagel reaction. Chin. J. Org. Chem. 2004, 24(2), 184-186.
    • (2004) Chin. J. Org. Chem. , vol.24 , Issue.2 , pp. 184-186
    • Xu, X.M.1    Li, Y.Q.2    Zhou, M.Y.3    Tan, Y.H.4
  • 22
    • 32244443296 scopus 로고    scopus 로고
    • The Knoevenagel reaction: Analysis and recycling of the ionic liquid medium
    • DOI 10.1016/j.tetlet.2006.01.059, PII S0040403906001158
    • Forbes, D. C.; Law, A. M.; Morrison, D. W. The Knoevenagel reaction: Analysis and recycling of the ionic liquid medium. Tetrahedron Lett. 2006, 47(11), 1699-1703. (Pubitemid 43212840)
    • (2006) Tetrahedron Letters , vol.47 , Issue.11 , pp. 1699-1703
    • Forbes, D.C.1    Law, A.M.2    Morrison, D.W.3
  • 24
    • 29144432829 scopus 로고    scopus 로고
    • 1-n-butyl-3-methylimmidazolium tetrafluoroborate-promoted green synthesis of 5-arylidene barbituric acids and thiobarbituric acid derivatives
    • DOI 10.1080/00397910500288254
    • Wang, C.; Ma, J. J.; Zhou, X.; Zang, X. H.; Wang, Z.; Gao, Y. J.; Cui, P. L. 1-n-Butyl-3-methylimmidazolium tetrafluoroborate-promoted green synthesis of 5-arylidene barbituric acids and thiobarbituric acids derivatives. Synth. Commun. 2005, 35(21), 2759-2764. (Pubitemid 41800886)
    • (2005) Synthetic Communications , vol.35 , Issue.21 , pp. 2759-2764
    • Wang, C.1    Ma, J.-J.2    Zhou, X.3    Zang, X.-H.4    Wang, Z.5    Gao, Y.-J.6    Cui, P.-L.7
  • 25
    • 38049129144 scopus 로고    scopus 로고
    • One-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by acidic ionic liquid
    • Ma, J. J.; Zang, X. H.; Zhou, X.; Wang, C.; Li, J. C.; Li, Q. One-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by acidic ionic liquid. Indian J. Chem., Sec. B 2007, 46B(12), 2045-2048.
    • (2007) Indian J. Chem., Sec. B , vol.46 B , Issue.12 , pp. 2045-2048
    • Ma, J.J.1    Zang, X.H.2    Zhou, X.3    Wang, C.4    Li, J.C.5    Li, Q.6
  • 26
    • 43049131781 scopus 로고    scopus 로고
    • Synthesis of 5-arylmethylidene-2-thio-4-thiazolidinone derivatives catalyzed by alkaline ionic liquid
    • Ma, J. J.; Gao, S. T.; Li, Z.; Tang, R. X.; Liu, H. Y.; Wang, C.; Gao, Y. Synthesis of 5-arylmethylidene-2-thio-4-thiazolidinone derivatives catalyzed by alkaline ionic liquid. Chin. J. Org. Chem. 2008, 28(2), 339-342.
    • (2008) Chin. J. Org. Chem. , vol.28 , Issue.2 , pp. 339-342
    • Ma, J.J.1    Gao, S.T.2    Li, Z.3    Tang, R.X.4    Liu, H.Y.5    Wang, C.6    Gao, Y.7
  • 27
    • 0037263218 scopus 로고    scopus 로고
    • A novel method for the synthesis of carboxylic esters catalyzed by expandable graphite
    • Zhang, Y. Q.; Wang, C.; Li, G. S. A novel method for the synthesis of carboxylic esters catalyzed by expandable graphite. Chin. Chem. Lett. 2003, 14(1), 17-19. (Pubitemid 36182868)
    • (2003) Chinese Chemical Letters , vol.14 , Issue.1 , pp. 17-19
    • Zhang, Y.Q.1    Wang, C.2    Li, G.S.3
  • 29
    • 0013188175 scopus 로고    scopus 로고
    • Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media
    • DOI 10.1016/S1566-7367(02)00087-0
    • Fraga-Dubreuil, J.; Bourahla, K.; Rahmouni, M.; Bazureau, J. P.; Hamelin, J. Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media. Catal. Commun. 2002, 35, 185-190. (Pubitemid 41087726)
    • (2002) Catalysis Communications , vol.3 , Issue.5 , pp. 185-190
    • Fraga-Dubreuil, J.1    Bourahla, K.2    Rahmouni, M.3    Bazureau, J.P.4    Hamelin, J.5
  • 30
    • 22244486653 scopus 로고    scopus 로고
    • Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles
    • DOI 10.1021/ol051004h
    • Ranu, B. C.; Banerjee, S. Ionic liquid as catalyst and reaction medium: The dramatic influence of task-specific ionic liquid, [bmim]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Org. Lett. 2005, 7(14), 3049-3052. (Pubitemid 40992628)
    • (2005) Organic Letters , vol.7 , Issue.14 , pp. 3049-3052
    • Ranu, B.C.1    Banerjee, S.2
  • 31
    • 8744251123 scopus 로고    scopus 로고
    • Knoevenagel condensation reaction catalyzed by functionalized ionic liquid 1-(2-hydroxyethyl)-3-methyl imidazolium chloride
    • Xu, X. M.; Li, Y. Q.; Zhou, M. Y. Knoevenagel condensation reaction catalyzed by functionalized ionic liquid 1-(2-hydroxyethyl)-3-methyl imidazolium chloride. Chin. J. Org. Chem. 2004, 24(10), 1253-1256.
    • (2004) Chin. J. Org. Chem. , vol.24 , Issue.10 , pp. 1253-1256
    • Xu, X.M.1    Li, Y.Q.2    Zhou, M.Y.3
  • 32
    • 0036736722 scopus 로고    scopus 로고
    • Anion exchange resin supported fluoride ion as a catalyst for the Knoevenagel condensation
    • Li, Y. Q.; Ye, H. H. Anion exchange resin supported fluoride ion as a catalyst for the Knoevenagel condensation. Chin. J. Org. Chem. 2002, 22(9), 678-680.
    • (2002) Chin. J. Org. Chem. , vol.22 , Issue.9 , pp. 678-680
    • Li, Y.Q.1    Ye, H.H.2
  • 33
    • 0001799142 scopus 로고
    • The Knoevenagel condensation catalyzed by potassium fluoride-alumina
    • Dai, G. Y.; Shi, D. Q.; Zhou, L. H. The Knoevenagel condensation catalyzed by potassium fluoride-alumina. Chin. J. Appl. Chem. 1995, 12(3), 103-104.
    • (1995) Chin. J. Appl. Chem. , vol.12 , Issue.3 , pp. 103-104
    • Dai, G.Y.1    Shi, D.Q.2    Zhou, L.H.3


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