메뉴 건너뛰기




Volumn 39, Issue 19, 2009, Pages 3500-3508

Ionic liquid, [bmim]Br, as an efficient promoting medium for synthesis of 3-acetoacetylcoumarin derivatives without the use of any catalyst

Author keywords

2 hydroxybenzaldehyde; 3 Acetoacetylcoumarin; 4 hydroxy 6 methyl 2H pyran 2 one; Ionic liquid

Indexed keywords

2 PYRONE DERIVATIVE; 3 ACETOACETYLCOUMARIN; 6 BROMO 3 ACETOACETYLCOUMARIN; 6 CHLORO 3 ACETOACETYLCOUMARIN; 6 METHOXY 3 ACETOACETYLCOUMARIN; 6 METHYL 3 ACETOACETYLCOUMARIN; 6,8 DI TERT BUTYL 3 ACETOACETYLCOUMARIN; 6,8 DIBROMO 3 ACETOACETYLCOUMARIN; 6,8 DICHLORO 3 ACETOACETYLCOUMARIN; 7 METHOXY 3 ACETOACETYLCOUMARIN; 8 METHOXY 3 ACETOACETYLCOUMARIN; BROMINE DERIVATIVE; COUMARIN DERIVATIVE; IONIC LIQUID; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

EID: 70349224458     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902779306     Document Type: Article
Times cited : (16)

References (39)
  • 1
    • 38949144732 scopus 로고    scopus 로고
    • An expedient microwave-assisted solvent-free solid-supported synthesis of pyrrolo[2,3-d]pyrimidine-pyrano[5,6-c] coumarin=[6,5-c]-chromone derivatives by intramolecular hetero Diels-Alder reaction
    • Ramesh, E.; Raghunathan, R. An expedient microwave-assisted, solvent-free, solid-supported synthesis of pyrrolo[2,3-d]pyrimidine-pyrano[5,6- c] coumarin=[6,5-c]-chromone derivatives by intramolecular hetero Diels-Alder reaction. Tetrahedron Lett. 2008, 49, 1812-1817.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1812-1817
    • Ramesh, E.1    Raghunathan, R.2
  • 2
    • 0021067758 scopus 로고
    • 2-(Aminomethyl)phenols, a new class of saluretic agents 5: Fused-ring analogues
    • Deana, A. A. 2-(Aminomethyl)phenols, a new class of saluretic agents, 5: Fused-ring analogues. J. Med. Chem. 1983, 26, 580-585.
    • (1983) J. Med. Chem. , vol.26 , pp. 580-585
    • Deana, A.A.1
  • 3
    • 0001008477 scopus 로고
    • Method of synthesis of b-methylfurans and a-methylene and b-methylene c-lactones-2 menthofuran syntheses
    • Wenkert, E.; Buckwalter, B. L. Method of synthesis of b-methylfurans and a-methylene and b-methylene c-lactones-2 menthofuran syntheses. J. Am. Chem. Soc. 1977, 99, 4778-4782.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4778-4782
    • Wenkert, E.1    Buckwalter, B.L.2
  • 6
    • 1642288258 scopus 로고    scopus 로고
    • Novel inhibitors of DNA gyrase: 3D structure-based biased needle screening, hit validation by biophysical methods, and 3D guided optimization: A promising alterative to random screening
    • Boehm, H. J.; Boehringer, M.; Bur, D.; Gmeunder, H.; Huber, W.; Klaus, W.; Kostrewa, D.; Kuehne, H.; Luebbers, T.; Meunier-Keller, N.; Mueller, F. Novel inhibitors of DNA gyrase: 3D structure-based biased needle screening, hit validation by biophysical methods, and 3D guided optimization: A promising alterative to random screening. J. Med. Chem. 2000, 43, 2664-2674.
    • (2000) J. Med. Chem. , vol.43 , pp. 2664-2674
    • Boehm, H.J.1    Boehringer, M.2    Bur, D.3    Gmeunder, H.4    Huber, W.5    Klaus, W.6    Kostrewa, D.7    Kuehne, H.8    Luebbers, T.9    Meunier-Keller, N.10    Mueller, F.11
  • 7
    • 0141632774 scopus 로고    scopus 로고
    • Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway
    • Tao, J.; Hu, S.; Pacholec, M.; Walsh, C. T. Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway. Org. Lett. 2003, 5, 3233-3236.
    • (2003) Org. Lett. , vol.5 , pp. 3233-3236
    • Tao, J.1    Hu, S.2    Pacholec, M.3    Walsh, C.T.4
  • 9
    • 33750357639 scopus 로고    scopus 로고
    • Synthesis and evaluation of coumermycin A1 analogues that inhibit the Hsp 90 protein folding machinery
    • Burlison, J. A.; Blagg, B. S. J. Synthesis and evaluation of coumermycin A1 analogues that inhibit the Hsp 90 protein folding machinery. Org. Lett. 2006, 8, 4855-4858.
    • (2006) Org. Lett. , vol.8 , pp. 4855-4858
    • Burlison, J.A.1    Blagg, B.S.J.2
  • 10
    • 11444268281 scopus 로고    scopus 로고
    • Synthetic and natural coumarins as cytotoxic agents
    • Kostova, I. Synthetic and natural coumarins as cytotoxic agents. Curr. Med. Chem. Anti-Cancer Agents 2005, 5, 29-46.
    • (2005) Curr. Med. Chem. Anti-Cancer Agents , vol.5 , pp. 29-46
    • Kostova, I.1
  • 11
    • 0034025357 scopus 로고    scopus 로고
    • Synthesis of some new coumarin-quinolone carboxylic acids
    • Trkovnik, M.; Ivezic, Z. Synthesis of some new coumarin-quinolone carboxylic acids. J. Heterocyclic Chem. 2000, 37, 137-141
    • (2000) J. Heterocyclic Chem. , vol.37 , pp. 137-141
    • Trkovnik, M.1    Ivezic, Z.2
  • 12
    • 4243115696 scopus 로고    scopus 로고
    • Heteroaromatization with 4-hydroxycoumarin. Part I: Synthesis of some new pyranocoumarins and coumarinopyranopyrimidines
    • El-Agrody, A. M.; Abd, E. M. S.; Fakery, A. H.; Bedair, A. H. Heteroaromatization with 4-hydroxycoumarin. Part I: Synthesis of some new pyranocoumarins and coumarinopyranopyrimidines. J. Chem. Res. Synop. 2000, 26-27.
    • (2000) J. Chem. Res. Synop. , pp. 26-27
    • El-Agrody, A.M.1    Abd, E.M.S.2    Fakery, A.H.3    Bedair, A.H.4
  • 13
    • 70349196209 scopus 로고
    • German Patent (East) DD
    • Hirsch, B.; Hoefgen, N. German Patent (East) DD 218,892, 1985.
    • (1985) , vol.218 , Issue.892
    • Hirsch, B.1    Hoefgen, N.2
  • 14
    • 4243530634 scopus 로고
    • Chem. Abstr. 1985, 103, 123357z.
    • (1985) Chem. Abstr. , vol.103
  • 15
    • 33749532486 scopus 로고    scopus 로고
    • Unexpected ring-opening of a 2-pyrone ring in the synthesis of 3-[(Z)-1-hydroxy-3-oxobut-1-enyl]-2H-chromene-2-one derivatives catalyzed by KF-alumina
    • Wang, X. S.; Zeng, Z. S.; Zhang, M. M.; Shi, D. Q.; Tu, S. J. Unexpected ring-opening of a 2-pyrone ring in the synthesis of 3-[(Z)-1-hydroxy-3-oxobut-1- enyl]-2H-chromene-2-one derivatives catalyzed by KF-alumina. J. Chem. Res., Synop. 2006, 602-604.
    • (2006) J. Chem. Res. Synop. , pp. 602-604
    • Wang, X.S.1    Zeng, Z.S.2    Zhang, M.M.3    Shi, D.Q.4    Tu, S.J.5
  • 16
    • 0342700246 scopus 로고    scopus 로고
    • A novel and direct synthetic route to substituted 1,5-dihydro-4H-[1] benzopyrano[4,3-b]pyridine-4,5-doiones
    • Svetlik, J.; Pronayava, N.; Hanus, V. A novel and direct synthetic route to substituted 1,5-dihydro-4H-[1]benzopyrano[4,3-b]pyridine-4,5-doiones. J. Heterocycl. Chem. 2000, 37, 395-399.
    • (2000) J. Heterocycl. Chem. , vol.37 , pp. 395-399
    • Svetlik, J.1    Pronayava, N.2    Hanus, V.3
  • 17
    • 0347091254 scopus 로고    scopus 로고
    • 2 systems
    • Dzyuba, S. V.; Bartsch, R. A. Recent advances in applications of room-temperature ionic liquid=supercritical CO2 systems. Angew. Chem. Int. Ed. 2003, 42, 148-150
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 148-150
    • Dzyuba, S.V.1    Bartsch, R.A.2
  • 18
    • 57249093659 scopus 로고    scopus 로고
    • A short history of ionic liquids-From molten salts to neoteric
    • Wilker, J. S. A short history of ionic liquids-From molten salts to neoteric. Green Chem. 2002, 4, 73-80.
    • (2002) Green Chem. , vol.4 , pp. 73-80
    • Wilker, J.S.1
  • 19
    • 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, 2071-2084
    • (1999) Chem. Rev. , vol.99 , pp. 2071-2084
    • Welton, T.1
  • 20
    • 0036809725 scopus 로고    scopus 로고
    • Ionic liquid (molten salt) phase organometallic catalysis
    • Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Ionic liquid (molten salt) phase organometallic catalysis. Chem. Rev. 2002, 102, 3667-3692.
    • (2002) Chem. Rev. , vol.102 , pp. 3667-3692
    • Dupont, J.1    De Souza, R.F.2    Suarez, P.A.Z.3
  • 21
    • 21844464282 scopus 로고    scopus 로고
    • Friedel-Crafts reactions in room temperature ionic liquids
    • Earle, M. J.; Seddon, K. R.; Adams, C. J.; Roberts, G. Friedel-Crafts reactions in room temperature ionic liquids. Chem. Commun. 1998, 2097-2098.
    • (1998) Chem. Commun. , pp. 2097-2098
    • Earle, M.J.1    Seddon, K.R.2    Adams, C.J.3    Roberts, G.4
  • 22
    • 0033593295 scopus 로고    scopus 로고
    • Diels-Alder reactions in room-temperature ionic liquids
    • DOI 10.1016/S0040-4039(98)02415-0, PII S0040403998024150
    • Fischer, T.; Sethi, A.; Welton, T.; Woolf, J. Diels-Alder reactions in room-temperature ionic liquids. Tetrahedron Lett. 1999, 40, 793-796 (Pubitemid 29059464)
    • (1999) Tetrahedron Letters , vol.40 , Issue.4 , pp. 793-796
    • Fischer, T.1    Sethi, A.2    Welton, T.3    Woolf, J.4
  • 23
    • 0033605852 scopus 로고    scopus 로고
    • Diels-Alder reactions in chloroaluminate ionic liquids: Acceleration and selectivity enhancement
    • Lee, C. W. Diels-Alder reactions in chloroaluminate ionic liquids: acceleration and selectivity enhancement. Tetrahedron Lett. 1999, 40, 2461-2464
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2461-2464
    • Lee, C.W.1
  • 24
    • 0035804480 scopus 로고    scopus 로고
    • Phosphonium tosylates as solvents for the Diels-Alder reaction
    • Ludley, P.; Karodia, N. Phosphonium tosylates as solvents for the Diels-Alder reaction. Tetrahedron Lett. 2001, 42, 2011-2014.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2011-2014
    • Ludley, P.1    Karodia, N.2
  • 26
    • 0034638784 scopus 로고    scopus 로고
    • Heck reaction in ionic liquids catalyzed by a Pd-benzothiazole carbine complex
    • Calo, V.; Nacci, A.; Lopez, L.; Mannarini, N. Heck reaction in ionic liquids catalyzed by a Pd-benzothiazole carbine complex. Tetrahedron Lett. 2000, 41, 8973-8976.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 8973-8976
    • Calo, V.1    Nacci, A.2    Lopez, L.3    Mannarini, N.4
  • 27
    • 0035944980 scopus 로고    scopus 로고
    • Coumarin synthesis via Pechmann condensation in Lewis acidic chloroaluminate ionic liquid
    • Potdar, M. K.; Mohile, S. S.; Salunkhe, M. M. Coumarin synthesis via Pechmann condensation in Lewis acidic chloroaluminate ionic liquid. Tetrahedron Lett. 2001, 42, 9285-9287.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 9285-9287
    • Potdar, M.K.1    Mohile, S.S.2    Salunkhe, M.M.3
  • 28
    • 0035920827 scopus 로고    scopus 로고
    • Ionic liquids catalyzed Biginelli reaction under solvent-free conditions
    • Peng, J.; Deng, Y. Ionic liquids catalyzed Biginelli reaction under solvent-free conditions. Tetrahedron Lett. 2001, 42, 5917-5919.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5917-5919
    • Peng, J.1    Deng, Y.2
  • 29
    • 0035955832 scopus 로고    scopus 로고
    • 5 in ionic liquids
    • Ren, R. X.; Zueva, L. D.; Ou, W. Formation of e-caprolactam via catalytic Beckmann rearrangement using P2O5 in ionic liquids. Tetrahedron Lett. 2001, 42, 8441-8443
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8441-8443
    • Ren, R.X.1    Zueva, L.D.2    Ou, W.3
  • 30
    • 0035862604 scopus 로고    scopus 로고
    • Catalytic Beckmann rearrangement of ketoximes in ionic liquids
    • Peng, J.; Deng, Y. Catalytic Beckmann rearrangement of ketoximes in ionic liquids. Tetrahedron Lett. 2001, 42, 403-405
    • (2001) Tetrahedron Lett. , vol.42 , pp. 403-405
    • Peng, J.1    Deng, Y.2
  • 31
    • 0000034575 scopus 로고    scopus 로고
    • Ionic liquids-New ''solvents'' for transition metal catalysis
    • Wasserscheid, P.; Keim, W. Ionic liquids-New ''solvents'' for transition metal catalysis. Angew. Chem. Int. Ed. 2000, 39, 3772-3789.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3772-3789
    • Wasserscheid, P.1    Keim, W.2
  • 32
    • 1842788687 scopus 로고    scopus 로고
    • Pyrrole synthesis in ionic liquids by Paal-Knorr condensation under mild conditions
    • Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, J. Pyrrole synthesis in ionic liquids by Paal-Knorr condensation under mild conditions. Tetrahedron Lett. 2004, 45, 3417-3419
    • (2004) Tetrahedron Lett. , vol.45 , pp. 3417-3419
    • Wang, B.1    Gu, Y.2    Luo, C.3    Yang, T.4    Yang, L.5    Suo, J.6
  • 33
    • 27744578648 scopus 로고    scopus 로고
    • Immobilized in ionic liquids
    • Yadav, J. S.; Reddy, B. V. S.; Baishya, G.; Reddy, K. V.; Narsaiah, A. V. Conjugate addition of indoles to a,b-unsatu-rated ketones using Cu(OTf)2 immobilized in ionic liquids. Tetrahedron 2005, 61, 9541-9544
    • (2005) Tetrahedron , vol.61 , pp. 9541-9544
    • Yadav, J.S.1    Reddy, B.V.S.2    Baishya, G.3    Reddy, K.V.4
  • 34
    • 0742304335 scopus 로고    scopus 로고
    • The first ionic liquids promoted conjugated addition of azide ion to a,b-unsatu-rated carbonyl compounds
    • Xu, L. W.; Li, L.; Xia, C. G.; Zhou, S. L.; Li, J. W. The first ionic liquids promoted conjugated addition of azide ion to a,b-unsatu-rated carbonyl compounds. Tetrahedron Lett. 2004, 45, 1219-1221.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1219-1221
    • Xu, L.W.1    Li, L.2    Xia, C.G.3    Zhou, S.L.4    Li, J.W.5
  • 35
    • 52249084125 scopus 로고    scopus 로고
    • 0-e]pyridines
    • Shi, D. Q.; Yang, F. Ionic liquid as an efficient promoting medium for synthesis of bis-pyrazolo[3,4-b:40,30-e]pyridines. J. Chin. Chem. Soc. 2008, 55, 755-760
    • (2008) J. Chin. Chem. Soc. , vol.55 , pp. 755-760
    • Shi, D.Q.1    Yang, F.2
  • 36
    • 44349151458 scopus 로고    scopus 로고
    • An efficient synthesis of polyhydroacridine derivatives by the three-component reaction of aldehydes, amines, and dimedione in ionic liquid
    • Shi, D. Q.; Ni, S. N.; Yang, F.; Shi, J. W.; Dou, G. L.; Li, X. Y.; Wang, X. S. An efficient synthesis of polyhydroacridine derivatives by the three-component reaction of aldehydes, amines, and dimedione in ionic liquid. J. Heterocyclic Chem. 2008, 45, 653-660
    • (2008) J. Heterocyclic Chem. , vol.45 , pp. 653-660
    • Shi, D.Q.1    Ni, S.N.2    Yang, F.3    Shi, J.W.4    Dou, G.L.5    Li, X.Y.6    Wang, X.S.7
  • 37
    • 44349089784 scopus 로고    scopus 로고
    • 0: 5,6]pyrido[2,3-d]pyrimidine derivatives via multicomponent reactions in ionic liquids
    • Shi, D. Q.; Ni, S. N.; Yang, F.; Shi, J. W.; Dou, G. L.; Li, X. L.; Wang, X. S.; Ji, S. J. An efficient synthesis of pyrimido[4,5-b]quinoline and indeno[20,10: 5,6]pyrido[2,3-d]pyrimidine derivatives via multicomponent reactions in ionic liquids. J. Heterocycl. Chem. 2008, 45, 693-702
    • (2008) J. Heterocycl. Chem. , vol.45 , pp. 693-702
    • Shi, D.Q.1    Ni, S.N.2    Yang, F.3    Shi, J.W.4    Dou, G.L.5    Li, X.L.6    Wang, X.S.7    Ji, S.J.8
  • 38
    • 51849100344 scopus 로고    scopus 로고
    • An efficient and green synthesis of 3,30-benzylidene-bis (4-hydroxy-6-methylpyridine 2(1H)-one) derivatives through multicompo-nent reaction in ionic liquid
    • Shi, D. Q.; Ni, S. N.; Yang, F.; Ji, S. J. An efficient and green synthesis of 3,30-benzylidene-bis (4-hydroxy-6-methylpyridine 2(1H)-one) derivatives through multicompo-nent reaction in ionic liquid. J. Heterocycl. Chem. 2008, 45, 1275-1280.
    • (2008) J. Heterocycl. Chem. , vol.45 , pp. 1275-1280
    • Shi, D.Q.1    Ni, S.N.2    Yang, F.3    Ji, S.J.4
  • 39
    • 0342997087 scopus 로고
    • Biogenetic-type synthesis of polyketides, part VIII: Experiments with the tetra-and hexa-acetate systems
    • Scott, A. L.; Guilford, H.; Ryan, J. J.; Skingle, D. Biogenetic-type synthesis of polyketides, part VIII: Experiments with the tetra-and hexa-acetate systems. Tetrahedron 1971, 27, 3025-3038.
    • (1971) Tetrahedron , vol.27 , pp. 3025-3038
    • Scott, A.L.1    Guilford, H.2    Ryan, J.J.3    Skingle, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.