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Volumn 10, Issue 1, 2013, Pages 8-11

A catalytic dual-activation approach to the significant 3,4-dihydropyrimidin-2(1H)-one system via the bignelli reaction

Author keywords

Biginelli reaction; Cooperative catalysis; DHPMs; Dihydropyrimidin 2(1H) one; DMAP; Dual activation; FeCl3; Lewis acid Lewis base system

Indexed keywords


EID: 84879805689     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017813805077299     Document Type: Article
Times cited : (8)

References (29)
  • 1
    • 0000176059 scopus 로고
    • Synthesis of 3, 4-dihydropyrimidin-2(1H)-ones
    • Biginelli, P. Synthesis of 3, 4-dihydropyrimidin-2(1H)-ones. Gazz. Chim. Ital., 1893, 23, 360-461.
    • (1893) Gazz. Chim. Ital. , vol.23 , pp. 360-461
    • Biginelli, P.1
  • 2
    • 0034518876 scopus 로고    scopus 로고
    • Recent advances in the Biginelli dihydro- pyrimidine synthesis. New tricks from an old dog
    • (a) Kappe, C. O. Recent advances in the Biginelli dihydro- pyrimidine synthesis. New tricks from an old dog. Acc. Chem. Res., 2000, 33, 879-888
    • (2000) Acc. Chem. Res. , vol.33 , pp. 879-888
    • Kappe, C.O.1
  • 3
    • 0001591221 scopus 로고    scopus 로고
    • Fluorous synthesis: Fluorous protocols for the Ugi and Biginelli multicom-ponent condensations
    • (b) Studer, A.; Jeger, P.; Curran, D. P. Fluorous synthesis: Fluorous protocols for the Ugi and Biginelli multicom-ponent condensations. J. Org.Chem., 1997, 62, 2917-2924.
    • (1997) J. Org.Chem. , vol.62 , pp. 2917-2924
    • Studer, A.1    Jeger, P.2    Curran, D.P.3
  • 4
    • 4644324512 scopus 로고    scopus 로고
    • Demonstration of the feasibility of a direct solid-phase split-pool Biginelli synthesis of 3, 4-dihydropyrimidinones
    • (a) Lusch, M. J.; Tallarico, J. A. Demonstration of the feasibility of a direct solid-phase split-pool Biginelli synthesis of 3, 4-dihydropyrimidinones. Org. Lett., 2004, 6, 3237-3240
    • (2004) Org. Lett. , vol.6 , pp. 3237-3240
    • Lusch, M.J.1    Tallarico, J.A.2
  • 5
    • 0034519777 scopus 로고    scopus 로고
    • Biologically active dihydripyrimidones of the bignelli-type. A literature survey
    • (b) Kappe, C. O. Biologically Active Dihydripyrimidones of the Bignelli-Type. A Literature Survey. Eur. J. Med. Chem., 2000, 35, 1043-1052.
    • (2000) Eur. J. Med. Chem. , vol.35 , pp. 1043-1052
    • Kappe, C.O.1
  • 6
    • 0033958880 scopus 로고    scopus 로고
    • Iron(III)-Catalyzed Synthesis of Dihydropyrimidi- nones. Improved Conditions for the Biginelli Reaction
    • Lu, J.; Ma, H. Iron(III)-Catalyzed Synthesis of Dihydropyrimidi- nones. Improved Conditions for the Biginelli Reaction. Synlett, 2000, 63-64.
    • (2000) Synlett , pp. 63-64
    • Lu, J.1    Ma, H.2
  • 7
    • 0032524801 scopus 로고    scopus 로고
    • Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3, 4-dihydropyrimidine- 2-(1H)-ones
    • Hu, E. H.; Sidler, D. R.; Dolling, U. H. Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3, 4-dihydropyrimidine- 2-(1H)-ones. J. Org. Chem., 1998, 63, 3454-3457.
    • (1998) J. Org. Chem. , vol.63 , pp. 3454-3457
    • Hu, E.H.1    Sidler, D.R.2    Dolling, U.H.3
  • 8
    • 0141768454 scopus 로고    scopus 로고
    • New environmentally friendly solvent free synthesis of di-hydropyrimidinones catalysed by N-butyl-N, N dimethylphenyleth-ylammonium bromide
    • Reddy, K. R.; Reddy, Ch. V.; Mahesh, M.; Raju, P.V.K.; Reddy, V.V.N. New environmentally friendly solvent free synthesis of di-hydropyrimidinones catalysed by N-butyl-N, N dimethylphenyleth-ylammonium bromide. Tetrahedron Lett., 2003, 44, 8173-8175.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 8173-8175
    • Reddy, K.R.1    Reddy Ch., V.2    Mahesh, M.3    Raju, P.V.K.4    Reddy, V.V.N.5
  • 9
    • 0034986934 scopus 로고    scopus 로고
    • Bismuth(III)- catalyzed synthesis of dihydropyrimidinones: Improved protocol conditions for the biginelli reaction
    • Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T. N. B. Bismuth(III)- Catalyzed Synthesis of Dihydropyrimidinones: Improved Protocol Conditions for the Biginelli Reaction. Synlett, 2001, 863-865.
    • (2001) Synlett , pp. 863-865
    • Ramalinga, K.1    Vijayalakshmi, P.2    Kaimal, T.N.B.3
  • 10
    • 0035969014 scopus 로고    scopus 로고
    • 2O-mediated three-component, one-pot, condensation reaction: An efficient synthesis of 4-aryl-substituted 3, 4-dihydropyrimidin-2-ones
    • 2O-mediated three-component, one-pot, condensation reaction: an efficient synthesis of 4-aryl-substituted 3, 4-dihydropyrimidin-2- ones. Tetrahedron Lett., 2001, 42, 7873-7875.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7873-7875
    • Kumar, K.A.1    Kasthuraiah, M.2    Reddy, C.S.3    Reddy, C.D.4
  • 11
    • 0034684498 scopus 로고    scopus 로고
    • One-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst
    • Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. One-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst. Tetrahedron Lett., 2000, 41, 9075-9078.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 9075-9078
    • Lu, J.1    Bai, Y.2    Wang, Z.3    Yang, B.4    Ma, H.5
  • 12
    • 0034703416 scopus 로고    scopus 로고
    • Indium(III) Chloride mediated Biginelli reactions
    • Brindaban, R.C.; Hajra, A.; Jana, U. Indium(III) Chloride mediated Biginelli reactions. J. Org. Chem., 2000, 65, 6270-6272.
    • (2000) J. Org. Chem. , vol.65 , pp. 6270-6272
    • Brindaban, R.C.1    Hajra, A.2    Jana, U.3
  • 13
    • 0037436897 scopus 로고    scopus 로고
    • 2: A reusable catalyst for high-yield synthesis of 3, 4-dihydropyrimidin-2(1H)- ones
    • 2: A reusable catalyst for high-yield synthesis of 3, 4-dihydropyrimidin-2(1H)- ones. Tetrahedron Lett., 2003, 44, 3305-3308.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3305-3308
    • Paraskar, A.S.1    Dewkar, G.K.2    Sudalai, A.3
  • 15
    • 0034674776 scopus 로고    scopus 로고
    • Lanthanide triflate catalyzed biginelli reaction. one-pot synthesis of dihydropyrimidino-nes under solvent-free conditions
    • Ma, Y.; Qian, C.; Wang, L.; Yang, M. Lanthanide Triflate Catalyzed Biginelli Reaction. One-Pot Synthesis of Dihydropyrimidino-nes under Solvent-Free Conditions. J. Org. Chem., 2000, 65 (12), 3864-3868.
    • (2000) J. Org. Chem. , vol.65 , Issue.12 , pp. 3864-3868
    • Ma, Y.1    Qian, C.2    Wang, L.3    Yang, M.4
  • 16
    • 0038752672 scopus 로고    scopus 로고
    • Lanthanide triflate catalyzed one-pot synthesis of dihydropyrimidin-2(1H) -thiones by a three component of 1, 3-dicarbonyl compounds, aldehydes, and thiourea using a solvent free Biginelli condensation
    • Wang, L.; Qian, C.; Tian, H.; Ma, Y. Lanthanide triflate catalyzed one-pot synthesis of dihydropyrimidin-2(1H)-thiones by a three component of 1, 3-dicarbonyl compounds, aldehydes, and thiourea using a solvent free Biginelli condensation. Synth. Commun., 2003, 33, 1459-1468.
    • (2003) Synth. Commun. , vol.33 , pp. 1459-1468
    • Wang, L.1    Qian, C.2    Tian, H.3    Ma, Y.4
  • 17
    • 2542465958 scopus 로고    scopus 로고
    • A highly efficient solvent-free synthesis of dihydropyrimidinones catalyzed by zinc chloride
    • Sun, Q.; Wang, Y.-q.; Ge, Z-m.; Cheng, T.-m.; Li, R-t. A Highly Efficient Solvent-Free Synthesis of Dihydropyrimidinones Catalyzed by Zinc Chloride. Synthesis, 2004, 7, 1047-1051
    • (2004) Synthesis , vol.7 , pp. 1047-1051
    • Sun, Q.1    Wang, Y.-Q.2    Ge, Z.-M.3    Cheng, T.-M.4    Li, R.-T.5
  • 18
    • 0036193521 scopus 로고    scopus 로고
    • Catalysis of the Biginelli Reaction by Ferric and Nickel Chloride Hexahydrates. One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones
    • (b) Lu, J.; Bai, Y. Catalysis of the Biginelli Reaction by Ferric and Nickel Chloride Hexahydrates. One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)- ones. Synthesis, 2002, 466-470.
    • (2002) Synthesis , pp. 466-470
    • Lu, J.1    Bai, Y.2
  • 19
    • 1342345161 scopus 로고    scopus 로고
    • A facile and efficient one-pot synthesis of dihydropyrimidinones catalyzed by magnesium bromide under solvent-free conditions
    • Salehi, H.; Guo, Q. X. A Facile and Efficient One-Pot Synthesis of Dihydropyrimidinones Catalyzed by Magnesium Bromide Under Solvent-Free Conditions. Synth. Commun., 2004, 34, 171-179.
    • (2004) Synth. Commun. , vol.34 , pp. 171-179
    • Salehi, H.1    Guo, Q.X.2
  • 20
    • 77951459592 scopus 로고    scopus 로고
    • Triethylamine Promoted Efficient Synthesis of 3, 4-Dihydropyrimidin- 2(1H)-ones/thiones Using a Solvent-Free Bigi-nelli Condensation
    • Debache, A.; Ghalem, W.; Boulcina, R.; Belfaitah, A.; Rhouati, S.; Carboni, B. Triethylamine Promoted Efficient Synthesis of 3, 4-Dihydropyrimidin- 2(1H)-ones/thiones Using a Solvent-Free Bigi-nelli Condensation. Letters in Organic Chemistry, 2010, 7 (4), 272-276.
    • (2010) Letters in Organic Chemistry , vol.7 , Issue.4 , pp. 272-276
    • Debache, A.1    Ghalem, W.2    Boulcina, R.3    Belfaitah, A.4    Rhouati, S.5    Carboni, B.6
  • 23
    • 0030732273 scopus 로고    scopus 로고
    • A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate
    • Kappe, C.O. A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate. J. Org. Chem., 1997, 62, 7201-7204.
    • (1997) J. Org. Chem. , vol.62 , pp. 7201-7204
    • Kappe, C.O.1
  • 24
    • 57349175964 scopus 로고    scopus 로고
    • An efficient and recycling catalyst for the one-pot three-component synthesis of substituted 3, 4 dihydropyrimidin-2(1h)-ones
    • Boumoud, T.; Boumoud, B.; Rhouati, S.; Belfaitah, A.; Debache, A.; Mosset, P. An Efficient and Recycling Catalyst for the One-Pot Three-Component Synthesis of Substituted 3, 4 Dihydropyrimidin-2(1H)-ones. E. J. Chem., 2008, 5, 688-695.
    • (2008) E. J. Chem. , vol.5 , pp. 688-695
    • Boumoud, T.1    Boumoud, B.2    Rhouati, S.3    Belfaitah, A.4    Debache, A.5    Mosset, P.6
  • 25
    • 20044380628 scopus 로고    scopus 로고
    • Indium (III) Tribromide: An Excellent Catalyst for Biginelli Reaction
    • Fu, N. Y.; Pang, M. L.; Yuan, Y. F.; Wang, J. T. Indium (III) Tribromide: An Excellent Catalyst for Biginelli Reaction, Chinese Chemical Letters, 2002, 13(10), 921-922.
    • (2002) Chinese Chemical Letters , vol.13 , Issue.10 , pp. 921-922
    • Fu, N.Y.1    Pang, M.L.2    Yuan, Y.F.3    Wang, J.T.4
  • 26
    • 0008005854 scopus 로고
    • Synthesis and Reactions of Biginelli-Compounds Part II. Nitration of 6-Methyl-2-oxo-1, 2, 3, 4-tetrahydro-5-pyrimidinecarboxylates
    • Kappe, C. O.; Wagner, U. G. Synthesis and Reactions of Biginelli-Compounds, Part II. Nitration of 6-Methyl-2-oxo-1, 2, 3, 4-tetrahydro-5-pyrimidinecarboxylates. Heterocycles, 1989, 29, 761-769.
    • (1989) Heterocycles , vol.29 , pp. 761-769
    • Kappe, C.O.1    Wagner, U.G.2
  • 27
    • 0032524801 scopus 로고    scopus 로고
    • Unprecedented Catalytic Three Component One-Pot Condensation Reaction: An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3, 4-dihydropyrimidin-2(1H)- ones
    • Hu, E.H.; Sidler, D. R.; Dolling, U.H. Unprecedented Catalytic Three Component One-Pot Condensation Reaction: An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3, 4-dihydropyrimidin-2(1H)-ones. J. Org. Chem., 1998, 63, 3454-3457.
    • (1998) J. Org. Chem. , vol.63 , pp. 3454-3457
    • Hu, E.H.1    Sidler, D.R.2    Dolling, U.H.3
  • 28
    • 54349110329 scopus 로고    scopus 로고
    • A Novel Catalyst for One-Pot Synthesis of Substituted 3, 4-Dihydropyrimidin-2-(1H)-ones via Biginelli Reaction, under Solvent-Free Conditions
    • Boumoud, T.; Boumoud, B.; Rhouati, S.; Belfaitah, A.; Debache, A.; Mosset, P. A Novel Catalyst for One-Pot Synthesis of Substituted 3, 4-Dihydropyrimidin-2-(1H)-ones via Biginelli Reaction, Under Solvent-Free Conditions. Acta. Chim. Slov., 2008, 55, 617-622.
    • (2008) Acta. Chim. Slov. , vol.55 , pp. 617-622
    • Boumoud, T.1    Boumoud, B.2    Rhouati, S.3    Belfaitah, A.4    Debache, A.5    Mosset, P.6
  • 29
    • 79951668679 scopus 로고    scopus 로고
    • Gypsum-Catalyzed One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H) under Solvent-Free Conditions
    • Boumoud, T.; Boumoud, B.; Mosset, P.; Debache, A. Gypsum-Catalyzed One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H) Under Solvent-Free Conditions. E-J. Chem., 2011, 8(1), 312-318. Recherche Scientifique
    • (2011) E-J. Chem. , vol.8 , Issue.1 , pp. 312-318
    • Boumoud, T.1    Boumoud, B.2    Mosset, P.3    Debache, A.4


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