메뉴 건너뛰기




Volumn 38, Issue 15, 2008, Pages 2646-2654

FeCl3-catalyzed Pechmann synthesis of coumarins in ionic liquids

Author keywords

Coumarins; Ionic liquids; Pachmann condensation; Recyclability

Indexed keywords

COUMARIN DERIVATIVE; FERRIC CHLORIDE; IONIC LIQUID;

EID: 51349109197     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802219569     Document Type: Article
Times cited : (46)

References (36)
  • 5
    • 18544407290 scopus 로고    scopus 로고
    • Chemoprevention of carcinogen-DNA binding: The relative role of different oxygenated substituents on 4-methylcoumarins in the inhibition of aflatoxin B1-DNA binding in vitro
    • (a) Raj, H. G. Gupta, S.; Biswas, G.; Singh, S.; Singh, A.; Jha, A.; Bisht, K. S. Sharma, S. K. Jain, S. C. Parmar, V. S. Chemoprevention of carcinogen-DNA binding: The relative role of different oxygenated substituents on 4-methylcoumarins in the inhibition of aflatoxin B1-DNA binding in vitro. Bioorg. Med. Chem. 1996, 4, 2225-2228;
    • (1996) Bioorg. Med. Chem , vol.4 , pp. 2225-2228
    • Raj, H.G.1    Gupta, S.2    Biswas, G.3    Singh, S.4    Singh, A.5    Jha, A.6    Bisht, K.S.7    Sharma, S.K.8    Jain, S.C.9    Parmar, V.S.10
  • 7
    • 13444278854 scopus 로고    scopus 로고
    • Novel thiocoumarins as inhibitors of TNF-α induced ICAM-1 expression on human umbilical vein endothelial cells (HUVECs) and microsomal lipid peroxidation
    • Kumar, S.; Singh, B. K. Kalra, N.; Kumar, V.; Kumar, A.; Prasad, A. K. Raj, H. G. Parmar, V. S. Ghosh, B. Novel thiocoumarins as inhibitors of TNF-α induced ICAM-1 expression on human umbilical vein endothelial cells (HUVECs) and microsomal lipid peroxidation. Bioorg. Med. Chem. 2005, 13, 1605-1613.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 1605-1613
    • Kumar, S.1    Singh, B.K.2    Kalra, N.3    Kumar, V.4    Kumar, A.5    Prasad, A.K.6    Raj, H.G.7    Parmar, V.S.8    Ghosh, B.9
  • 8
    • 0002091136 scopus 로고
    • The Pechmann reaction
    • Sethna, S.; Phadke, R. The Pechmann reaction. Org. React. 1953, 7, 1-58.
    • (1953) Org. React , vol.7 , pp. 1-58
    • Sethna, S.1    Phadke, R.2
  • 9
    • 0000989392 scopus 로고
    • Perkin reaction and related reactions
    • Johnson, J. R. Perkin reaction and related reactions. Org. React. 1942, 1, 210-265.
    • (1942) Org. React , vol.1 , pp. 210-265
    • Johnson, J.R.1
  • 10
    • 0000248247 scopus 로고
    • Knoevenagel condensation
    • (a) Jones, G. Knoevenagel condensation. Org. React. 1967, 15, 204-599;
    • (1967) Org. React , vol.15 , pp. 204-599
    • Jones, G.1
  • 11
    • 0000941772 scopus 로고    scopus 로고
    • Simple and efficient one-pot preparation of 3-substituted coumarins in water
    • (b) Brufola, G.; Fringuelli, F.; Piermatti, O.; Pizzo, F. Simple and efficient one-pot preparation of 3-substituted coumarins in water. Heterocycles 1996, 43, 1257-1266.
    • (1996) Heterocycles , vol.43 , pp. 1257-1266
    • Brufola, G.1    Fringuelli, F.2    Piermatti, O.3    Pizzo, F.4
  • 12
    • 0002847120 scopus 로고
    • Reformatsky reaction
    • Shriner, R. L. Reformatsky reaction. Org. React. 1942, 1, 1-35.
    • (1942) Org. React , vol.1 , pp. 1-35
    • Shriner, R.L.1
  • 13
    • 85067355181 scopus 로고
    • Synthetic application of lithiation reactions, part XIII: Synthesis of 3-phenylcoumarins and their benzo derivatives
    • (a) Narasimhan, N. S. Mali, R. S. Barve, M. V. Synthetic application of lithiation reactions, part XIII: Synthesis of 3-phenylcoumarins and their benzo derivatives. Synthesis 1979, 906-909;
    • (1979) Synthesis , pp. 906-909
    • Narasimhan, N.S.1    Mali, R.S.2    Barve, M.V.3
  • 14
    • 0032537144 scopus 로고    scopus 로고
    • A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenyl-phosphonium salt
    • (b) Yavari, I.; Hekmat-Shoar, R.; Zonouzi, A. A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenyl-phosphonium salt. Tetrahedron Lett. 1998, 39, 2391-2392.
    • (1998) Tetrahedron Lett , vol.39 , pp. 2391-2392
    • Yavari, I.1    Hekmat-Shoar, R.2    Zonouzi, A.3
  • 15
    • 0001933901 scopus 로고
    • 2,4-Dihydroxyacetophenone
    • Russell, A.; Frye, J. R. 2,4-Dihydroxyacetophenone. Org. Synth. 1941, 21, 22-27.
    • (1941) Org. Synth , vol.21 , pp. 22-27
    • Russell, A.1    Frye, J.R.2
  • 16
    • 37049144923 scopus 로고
    • Hydroxycarbonyl compounds, V: Preparation of coumarins and 1,4-pyrones from phenol, p-cresol, quinol, and α-naphthol
    • Robertson, A.; Sandrocik, W. F. Hendry, C. B. Hydroxycarbonyl compounds, V: Preparation of coumarins and 1,4-pyrones from phenol, p-cresol, quinol, and α-naphthol. J. Chem. Soc. 1931, 2426-2432.
    • (1931) J. Chem. Soc , pp. 2426-2432
    • Robertson, A.1    Sandrocik, W.F.2    Hendry, C.B.3
  • 17
    • 37049174330 scopus 로고
    • Aluminum chloride, a new reagent for the condensation of β-ketonic esters with phenols, I: The condensation of methyl β-resorcylate, β-resorcylic acid, and resacetophenone with ethyl acetoacetate
    • Sethna, S.; Shah, N. M. Shah, R. C. Aluminum chloride, a new reagent for the condensation of β-ketonic esters with phenols, I: The condensation of methyl β-resorcylate, β-resorcylic acid, and resacetophenone with ethyl acetoacetate. J. Chem. Soc. 1938, 228-232.
    • (1938) J. Chem. Soc , pp. 228-232
    • Sethna, S.1    Shah, N.M.2    Shah, R.C.3
  • 18
    • 33947472724 scopus 로고
    • New one-step synthesis of substituted coumarins
    • Woods, L. L. Sapp, J. New one-step synthesis of substituted coumarins. J. Org. Chem. 1962, 27, 3703-3705.
    • (1962) J. Org. Chem , vol.27 , pp. 3703-3705
    • Woods, L.L.1    Sapp, J.2
  • 21
    • 0035832091 scopus 로고    scopus 로고
    • Microwave acceleration of the Pechmann reaction on graphite/montmorillonite K10: Application to the preparation of 4-substituted 7-aminocoumarins
    • Frère, S.; Thiéry, V.; Besson, T. Microwave acceleration of the Pechmann reaction on graphite/montmorillonite K10: Application to the preparation of 4-substituted 7-aminocoumarins. Tetrahedron Lett. 2001, 42, 2791-2794.
    • (2001) Tetrahedron Lett , vol.42 , pp. 2791-2794
    • Frère, S.1    Thiéry, V.2    Besson, T.3
  • 22
    • 33644839527 scopus 로고    scopus 로고
    • Microwave-initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation
    • Manhas, M. S. Ganguly, S. N. Mukherjee, S.; Jain, A. K. Bose, A. K. Microwave-initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation. Tetrahedron Lett. 2006, 47, 2423-2425.
    • (2006) Tetrahedron Lett , vol.47 , pp. 2423-2425
    • Manhas, M.S.1    Ganguly, S.N.2    Mukherjee, S.3    Jain, A.K.4    Bose, A.K.5
  • 23
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids: Solvents for synthesis and catalysis
    • (a) Welton, T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2083;
    • (1999) Chem. Rev , vol.99 , pp. 2071-2083
    • Welton, T.1
  • 24
    • 0036998098 scopus 로고    scopus 로고
    • Zhao, H.; Malhotra, S. V. application of ionic liquids in organic synthesis. Aldrichimica Acta 2002, 35, 75-83;
    • (b) Zhao, H.; Malhotra, S. V. application of ionic liquids in organic synthesis. Aldrichimica Acta 2002, 35, 75-83;
  • 25
    • 12344296667 scopus 로고    scopus 로고
    • Chemical and biochemical transformations in ionic liquids
    • Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Chemical and biochemical transformations in ionic liquids. Tetrahedron 2005, 61, 1015-1060.
    • (2005) Tetrahedron , vol.61 , pp. 1015-1060
    • Jain, N.1    Kumar, A.2    Chauhan, S.3    Chauhan, S.M.S.4
  • 26
    • 0036139145 scopus 로고    scopus 로고
    • Pechmann reaction in chloroaluminate ionic liquid
    • (a) Khandekar, A. C. Khadilkar, B. M. Pechmann reaction in chloroaluminate ionic liquid. Synlett 2002, 152-154;
    • (2002) Synlett , pp. 152-154
    • Khandekar, A.C.1    Khadilkar, B.M.2
  • 27
    • 0035944980 scopus 로고    scopus 로고
    • Coumarin syntheses via Pechmann condensation in Lewis acidic chloroaluminate ionic liquid
    • (b) Potdar, M. K. Mohile, S. S. Salunkhe, M. M. Coumarin syntheses 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
    • 20344387001 scopus 로고    scopus 로고
    • Convenient and efficient protocols for coumarin synthesis via Pechmann condensation in neutral ionic liquids
    • Potdar, M. K. Rasalkar, M. S. Mohile, S. S. Salunkhe, M. M. Convenient and efficient protocols for coumarin synthesis via Pechmann condensation in neutral ionic liquids. J. Mol. Catl. A: Chem. 2005, 235, 249-252.
    • (2005) J. Mol. Catl. A: Chem , vol.235 , pp. 249-252
    • Potdar, M.K.1    Rasalkar, M.S.2    Mohile, S.S.3    Salunkhe, M.M.4
  • 29
    • 22944465724 scopus 로고    scopus 로고
    • Friedel-Crafts acylation reactions in pyridinium based ionic liquids
    • (a) Xiao, Y.; Malhotra, S. V. Friedel-Crafts acylation reactions in pyridinium based ionic liquids. J. Organometall. Chem. 2005, 690, 3609-3613;
    • (2005) J. Organometall. Chem , vol.690 , pp. 3609-3613
    • Xiao, Y.1    Malhotra, S.V.2
  • 30
    • 14644445148 scopus 로고    scopus 로고
    • Friedel-Crafts alkylation reactions in pyridinium-based ionic liquids
    • (b) Xiao, Y.; Malhotra, S. V. Friedel-Crafts alkylation reactions in pyridinium-based ionic liquids. J. Mol. Cat. A: Chem. 2005, 230, 129-133.
    • (2005) J. Mol. Cat. A: Chem , vol.230 , pp. 129-133
    • Xiao, Y.1    Malhotra, S.V.2
  • 31
    • 34247850688 scopus 로고    scopus 로고
    • 3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions
    • 3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions. Tetahedron Lett. 2007, 48, 4065-4069.
    • (2007) Tetahedron Lett , vol.48 , pp. 4065-4069
    • Jana, U.1    Biswas, S.2    Maiti, S.3
  • 32
    • 20444447641 scopus 로고    scopus 로고
    • Green methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid
    • (a) Prasad, A. K. Kumar, V.; Malhotra, S.; Ravikumar, V. T. Sanghvi, Y. S. Parmar, V. S. Green methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid. Bioorg. Med. Chem. 2005, 13, 4467-4472;
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 4467-4472
    • Prasad, A.K.1    Kumar, V.2    Malhotra, S.3    Ravikumar, V.T.4    Sanghvi, Y.S.5    Parmar, V.S.6
  • 33
    • 33845913229 scopus 로고    scopus 로고
    • Enhanced solubility and selective benzoylation of nucleosides in novel ionic liquid
    • (b) Kumar, V.; Parmar, V. S. Malhotra, S. V. Enhanced solubility and selective benzoylation of nucleosides in novel ionic liquid. Tetrahedron Lett. 2007, 48, 809-812.
    • (2007) Tetrahedron Lett , vol.48 , pp. 809-812
    • Kumar, V.1    Parmar, V.S.2    Malhotra, S.V.3
  • 34
    • 13144257725 scopus 로고    scopus 로고
    • Room-temperature ionic liquids that dissolve carbohydrates in high concentrations
    • Liu, Q.; Janssen, M. H. A. van Rantwijk, F.; Sheldon, R. A. Room-temperature ionic liquids that dissolve carbohydrates in high concentrations. Green Chem. 2005, 7, 39-42.
    • (2005) Green Chem , vol.7 , pp. 39-42
    • Liu, Q.1    Janssen, M.H.A.2    van Rantwijk, F.3    Sheldon, R.A.4
  • 35
    • 4644300447 scopus 로고    scopus 로고
    • Samarium(III)-catalyzed one-pot construction of coumarins
    • Bahekar, S. S. Shinde, D. B. Samarium(III)-catalyzed one-pot construction of coumarins. Tetrahedron Lett. 2004, 45, 7999-8001.
    • (2004) Tetrahedron Lett , vol.45 , pp. 7999-8001
    • Bahekar, S.S.1    Shinde, D.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.