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Volumn 15, Issue 5, 2010, Pages 2949-2961

Regioselective Suzuki-Miyaura reaction: Application to the microwave-promoted synthesis of 4,7-diarylquinazolines

Author keywords

Microwaves; Quinazoline; SRN1; Suzuki Miyaura reaction

Indexed keywords

DRUG; QUINAZOLINE DERIVATIVE;

EID: 77952840496     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15052949     Document Type: Article
Times cited : (20)

References (37)
  • 1
    • 49249152617 scopus 로고
    • A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides
    • Miyaura, N.; Yamada, K.; Suzuki, A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett. 1979, 20, 3437-3440.
    • (1979) Tetrahedron Lett. , vol.20 , pp. 3437-3440
    • Miyaura, N.1    Yamada, K.2    Suzuki, A.3
  • 2
    • 37049107259 scopus 로고
    • Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst
    • Miyaura, N.; Suzuki, A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. J. Chem. Soc. Chem. Commun. 1979, 866-867.
    • (1979) J. Chem. Soc. Chem. Commun. , pp. 866-867
    • Miyaura, N.1    Suzuki, A.2
  • 3
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 4
    • 0002812967 scopus 로고    scopus 로고
    • Organoboron compounds
    • Miyaura, N. Organoboron Compounds. Top. Curr. Chem. 2002, 219, 11-59.
    • (2002) Top. Curr. Chem. , vol.219 , pp. 11-59
    • Miyaura, N.1
  • 6
    • 0346786657 scopus 로고    scopus 로고
    • Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998
    • Suzuki, A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998. J. Organomet. Chem. 1999, 576, 147-168.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 147-168
    • Suzuki, A.1
  • 7
    • 33646456316 scopus 로고    scopus 로고
    • Regioselective dicouplings: Application to differentially substituted pyrroles
    • Handy, S. T.; Sabatini, J.J. Regioselective Dicouplings: Application to Differentially Substituted Pyrroles. Org. Lett. 2006, 8, 1537-1537.
    • (2006) Org. Lett. , vol.8 , pp. 1537-1537
    • Handy, S.T.1    Sabatini, J.J.2
  • 8
    • 36348953849 scopus 로고    scopus 로고
    • New efficient route to dissymmetric 2,4-Di(het)aryl-pyrido[3,2-d] pyrimidines via regioselective cross-coupling reactions
    • Tikad, A.; Routier, S.; Akssira, M.; Leger, J.-M.; Jarry, C.; Guillaumet, G. New Efficient Route to Dissymmetric 2,4-Di(het)aryl-pyrido[3,2-d]pyrimidines via Regioselective Cross-Coupling Reactions. Org. Lett. 2007, 9, 4673-4676.
    • (2007) Org. Lett. , vol.9 , pp. 4673-4676
    • Tikad, A.1    Routier, S.2    Akssira, M.3    Leger, J.-M.4    Jarry, C.5    Guillaumet, G.6
  • 9
    • 0033486308 scopus 로고    scopus 로고
    • Quinoline, quinazoline and acridone alkaloids.
    • Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 1999, 16, 697-709.
    • (1999) Nat. Prod. Rep. , vol.16 , pp. 697-709
    • Michael, J.P.1
  • 13
    • 41349085423 scopus 로고    scopus 로고
    • Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anticancer activity (cytotoxic) against U937 leukemia cell lines
    • Chandrika, P.M.; Yakaiah, T.; Ram Rao, A.R.; Narsaiah, B.; Reddy, N.C.; Sridhar, V.; Rao, J.V. Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anticancer activity (cytotoxic) against U937 leukemia cell lines. Eur. J. Med. Chem. 2008, 43, 846-852.
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 846-852
    • Chandrika, P.M.1    Yakaiah, T.2    Ram Rao, A.R.3    Narsaiah, B.4    Reddy, N.C.5    Sridhar, V.6    Rao, J.V.7
  • 17
    • 34447097175 scopus 로고    scopus 로고
    • Microwave-assisted synthesis in water as solvent
    • Dallinger, D.; Kappe, C.O. Microwave-Assisted Synthesis in Water as Solvent. Chem. Rev. 2007, 107, 2563-2591.
    • (2007) Chem. Rev. , vol.107 , pp. 2563-2591
    • Dallinger, D.1    Kappe, C.O.2
  • 18
    • 0041570557 scopus 로고    scopus 로고
    • Direct synthesis of unprotected 4-aryl phenylalanines via the suzuki reaction under microwave irradiation
    • Gong, Y.; He, W. Direct Synthesis of Unprotected 4-Aryl Phenylalanines via the Suzuki Reaction under Microwave Irradiation. Org. Lett. 2002, 4, 3803-3805.
    • (2002) Org. Lett. , vol.4 , pp. 3803-3805
    • Gong, Y.1    He, W.2
  • 19
    • 14544289090 scopus 로고    scopus 로고
    • Microwave-promoted heck coupling using ultralow metal catalyst concentrations
    • Arvela, R.K.; Leadbeater, N.E. Microwave-Promoted Heck Coupling Using Ultralow Metal Catalyst Concentrations. J. Org. Chem. 2005, 70, 1786-1790.
    • (2005) J. Org. Chem. , vol.70 , pp. 1786-1790
    • Arvela, R.K.1    Leadbeater, N.E.2
  • 20
    • 33646568471 scopus 로고    scopus 로고
    • Rapid microwave-promoted synthesis of new sulfonylmethylbenzothiazoles in water
    • DOI 10.1039/b601452f
    • Gellis, A.; Boufatah, N.; Vanelle, P. Rapid microwave-promoted synthesis of new sulfonylmethylbenzothiazoles in water. Green Chem. 2006, 8, 483-487. (Pubitemid 43725939)
    • (2006) Green Chemistry , vol.8 , Issue.5 , pp. 483-487
    • Gellis, A.1    Boufatah, N.2    Vanelle, P.3
  • 21
    • 0035931419 scopus 로고    scopus 로고
    • Microwave mediated palladium-catalysed reactions on potassium fluoride/alumina without use of solvent
    • Villemin, D.; Caillot, F. Microwave mediated palladium-catalysed reactions on potassium fluoride/alumina without use of solvent. Tetrahedron Lett. 2001, 42, 639-642.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 639-642
    • Villemin, D.1    Caillot, F.2
  • 22
    • 0035742525 scopus 로고    scopus 로고
    • Solvent-free accelerated organic syntheses using microwaves
    • Varma, R.S. Solvent-free accelerated organic syntheses using microwaves. Pure Appl. Chem. 2001, 73, 193-198.
    • (2001) Pure Appl. Chem. , vol.73 , pp. 193-198
    • Varma, R.S.1
  • 23
    • 13244273376 scopus 로고    scopus 로고
    • Synthesis of phosphonium salts under microwave activation - Leaving group and phosphine substituents effects
    • Cvengros, A.; Toma, S.; Marque, S.; Loupy, A. Synthesis of phosphonium salts under microwave activation - Leaving group and phosphine substituents effects. Can. J. Chem. 2004, 82, 1365-1371.
    • (2004) Can. J. Chem. , vol.82 , pp. 1365-1371
    • Cvengros, A.1    Toma, S.2    Marque, S.3    Loupy, A.4
  • 24
    • 17744385778 scopus 로고    scopus 로고
    • Microwave-assisted Suzuki reactions in a continuous flow capillary reactor
    • He, P.; Haswell, S.J.; Fletcher, D.I. Microwave-assisted Suzuki reactions in a continuous flow capillary reactor. Appl. Catal. A Gen. 2004, 274, 111-114.
    • (2004) Appl. Catal. A Gen. , vol.274 , pp. 111-114
    • He, P.1    Haswell, S.J.2    Fletcher, D.I.3
  • 25
    • 33947731107 scopus 로고    scopus 로고
    • Microwave assisted asymmetric Suzuki-Miyaura and Negishi cross-coupling reactions: Synthesis of chiral binaphthalenes
    • Genov, M.; Almorin, A.; Espinet, P. Microwave assisted asymmetric Suzuki-Miyaura and Negishi cross-coupling reactions: Synthesis of chiral binaphthalenes. Tetrahedron Asymmetry 2007, 18, 625-627.
    • (2007) Tetrahedron Asymmetry , vol.18 , pp. 625-627
    • Genov, M.1    Almorin, A.2    Espinet, P.3
  • 26
    • 68349088939 scopus 로고    scopus 로고
    • Synthesis of original 2-substituted 4-arylquinazolines by microwave-irradiated Suzuki-Miyaura cross-coupling reactions
    • Kabri, Y.; Gellis, A.; Vanelle, P. Synthesis of original 2-substituted 4-arylquinazolines by microwave-irradiated Suzuki-Miyaura cross-coupling reactions. Eur. J. Org. Chem. 2009, 4059-4066.
    • (2009) Eur. J. Org. Chem. , pp. 4059-4066
    • Kabri, Y.1    Gellis, A.2    Vanelle, P.3
  • 27
    • 0030039957 scopus 로고    scopus 로고
    • Trialkylalanes in palladium-catalyzed chemo- and regioselective alkylations
    • Mangalagiu, I.; Benneche, T.; Undheim, K. Trialkylalanes in palladium-catalyzed chemo- and regioselective alkylations. Tetrahedron Lett. 1996, 37, 1309-1312.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1309-1312
    • Mangalagiu, I.1    Benneche, T.2    Undheim, K.3
  • 28
    • 34948830110 scopus 로고    scopus 로고
    • A concise synthesis of quinazolinone TGF-β RI inhibitor through one-pot three-component Suzuki-Miyaura/etherification and imidate-amide rearrangement reactions
    • Li, H.; Wang, Y.; McMillen, W.T.; Chatterjee, A.; Toth, J.E.; Mundla, S.R.; Voss, M.; Boyer, R.D.; Sawyer, J.S. A concise synthesis of quinazolinone TGF-β RI inhibitor through one-pot three-component Suzuki-Miyaura/ etherification and imidate-amide rearrangement reactions. Tetrahedron 2007, 63, 11763-11770.
    • (2007) Tetrahedron , vol.63 , pp. 11763-11770
    • Li, H.1    Wang, Y.2    McMillen, W.T.3    Chatterjee, A.4    Toth, J.E.5    Mundla, S.R.6    Voss, M.7    Boyer, R.D.8    Sawyer, J.S.9
  • 29
    • 0037112673 scopus 로고    scopus 로고
    • Palladium-catalyzed coupling reactions of aryl chlorides
    • Littke, A.F.; Fu, G.C. Palladium-Catalyzed Coupling Reactions of Aryl Chlorides. Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4176-4211
    • Littke, A.F.1    Fu, G.C.2
  • 30
    • 67349136549 scopus 로고    scopus 로고
    • Microwave-assisted synthesis in aqueous medium of new quinazoline derivatives as anticancer agent precursors
    • Kabri, Y.; Gellis, A.; Vanelle, P. Microwave-assisted synthesis in aqueous medium of new quinazoline derivatives as anticancer agent precursors. Green Chem. 2009, 11, 201-208.
    • (2009) Green Chem. , vol.11 , pp. 201-208
    • Kabri, Y.1    Gellis, A.2    Vanelle, P.3
  • 32
    • 68849083988 scopus 로고    scopus 로고
    • [Chem. Abstr. 2007, 147, 427370].
    • (2007) Chem. Abstr. , vol.147 , pp. 427370
  • 35
    • 4644223893 scopus 로고    scopus 로고
    • Preparation and resolution of a modular class of axially chiral quinazoline-containing ligands and their application in asymmetric rhodium-catalyzed olefin hydroboration
    • Conolly, D.J.; Lacey, P.M.; Mc Carthy, M.; Saunders, C.P.; Carroll, A.-M.; Goddard, R.; Guiry, P.J. Preparation and Resolution of a Modular Class of Axially Chiral Quinazoline-Containing Ligands and Their Application in Asymmetric Rhodium-Catalyzed Olefin Hydroboration. J. Org. Chem. 2004, 69, 6572-6589.
    • (2004) J. Org. Chem. , vol.69 , pp. 6572-6589
    • Conolly, D.J.1    Lacey, P.M.2    McCarthy, M.3    Saunders, C.P.4    Carroll, A.-M.5    Goddard, R.6    Guiry, P.J.7
  • 36
    • 43849091460 scopus 로고    scopus 로고
    • Suzuki-Miyaura cross-coupling of α-phosphoryloxy enol ethers with arylboronic acids
    • Pedzisa, L.; Vaughn, I.W.; Pongdee, R. Suzuki-Miyaura cross-coupling of α-phosphoryloxy enol ethers with arylboronic acids. Tetrahedron Lett. 2008, 49, 4142-4144.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4142-4144
    • Pedzisa, L.1    Vaughn, I.W.2    Pongdee, R.3


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