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Volumn 15, Issue 4, 2011, Pages 833-837

One-pot synthesis of 1,2,3-triazole linked dihydropyrimidinones via Huisgen 1,3-dipolar/Biginelli cycloaddition

Author keywords

1. 2. 3 Triazole; Biginelli; Click chemistry; Dihydropyrimidinone; Multicomponent reaction; One pot reaction

Indexed keywords

PYRIMIDINONE DERIVATIVE; TRIAZOLE DERIVATIVE;

EID: 85027933243     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9313-6     Document Type: Article
Times cited : (32)

References (35)
  • 3
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed 41:2596-2599. doi:10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 4
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • doi:10.1002/1521-3773(20010601
    • Kolb HC, FinnMG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40:2004-2021. doi:10.1002/1521-3773(20010601)
    • (2001) Angew Chem Int Ed , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 6
    • 0345306644 scopus 로고    scopus 로고
    • Rapid Diversity-Oriented Synthesis in Microtiter Plates for in Situ Screening of HIV Protease Inhibitors
    • DOI 10.1002/cbic.200300724
    • Brik A, Muldoon J, Lin YC, Elder JH, Goodsell DS, Olson AJ, Fokin V, Sharpless KB,Wong CH (2003) Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors. ChemBioChem 4:1246-1248. doi:10.1002/cbic.200300724 (Pubitemid 37462831)
    • (2003) ChemBioChem , vol.4 , Issue.11 , pp. 1246-1248
    • Brik, A.1    Muldoon, J.2    Lin, Y.-C.3    Elder, J.H.4    Goodsell, D.S.5    Olson, A.J.6    Fokin, V.V.7    Sharpless, K.B.8    Wong, C.-H.9
  • 8
    • 0037462106 scopus 로고    scopus 로고
    • Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition
    • DOI 10.1021/ja034490h
    • Speers AE, Adam GC, Cravatt BF (2003) Activity-based protein profiling in vivo using a copper(I) catalyzed azide-alkyne [3 +2] cycloaddition. J Am Chem Soc 125:4686-4687. doi:10.1021/ja034490h (Pubitemid 36505343)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.16 , pp. 4686-4687
    • Speers, A.E.1    Adam, G.C.2    Cravatt, B.F.3
  • 9
    • 0041692305 scopus 로고    scopus 로고
    • Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3+2] cycloaddition
    • DOI 10.1021/ja036765z
    • Link AJ, Tirell DA (2003) Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3+2] cycloaddition. J Am Chem Soc 125:11164-11165. doi:10.1021/ja036765z (Pubitemid 37108030)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.37 , pp. 11164-11165
    • Link, A.J.1    Tirrell, D.A.2
  • 14
    • 23844451374 scopus 로고    scopus 로고
    • The convergence of synthetic organic and polymer chemistries
    • DOI 10.1126/science.1109778
    • Hawker CJ, Wooley KL (2005) The convergence of synthetic organic and polymer chemistries. Science 309:1200-1205. doi:10. 1126/science.1109778 (Pubitemid 41170906)
    • (2005) Science , vol.309 , Issue.5738 , pp. 1200-1205
    • Hawker, C.J.1    Wooley, K.L.2
  • 15
    • 34247863738 scopus 로고    scopus 로고
    • Azide-modified graphitic surfaces for covalent attachment of alkyne-terminated molecules by "click" chemistry
    • DOI 10.1021/ja071291f
    • Devadoss A, Chidsey CED (2007) Azide-modified graphitic surfaces for covalent attachment of alkyne-terminated molecules by "click" chemistry. J Am Chem Soc 129:5370-5371. doi:10.1021/ja071291f (Pubitemid 46697619)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.17 , pp. 5370-5371
    • Devadoss, A.1    Chidsey, C.E.D.2
  • 16
    • 8344250171 scopus 로고    scopus 로고
    • Towards organo-click chemistry: Development of organocatalytic multicomponent reactions through combinations of aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions
    • doi:10.1002/chem.200400597
    • Ramachary DB, Barbas CFIII (2004) Towards organo-click chemistry: development of organocatalytic multicomponent reactions through combinations of aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions. Chem Eur J 10:5323-5331. doi:10.1002/chem.200400597
    • (2004) Chem Eur J , vol.10 , pp. 5323-5331
    • Ramachary, D.B.1    Cfiii, B.2
  • 17
    • 5644259644 scopus 로고    scopus 로고
    • A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions
    • DOI 10.1016/j.tetlet.2004.09.117, PII S0040403904020854
    • Akritopoulou-Zanze I, Gracias V, Djuric SW (2004) A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyneazide cycloaddition reactions. Tetrahedron Lett 45:8439-8441. doi:10.1016/j.tetlet.2004.09.117 (Pubitemid 39369885)
    • (2004) Tetrahedron Letters , vol.45 , Issue.46 , pp. 8439-8441
    • Akritopoulou-Zanze, I.1    Gracias, V.2    Djuric, S.W.3
  • 18
    • 28244440237 scopus 로고    scopus 로고
    • Synthesis of fused triazolo-imidazole derivatives by sequential van Leusen/alkyne-azide cycloaddition reactions
    • DOI 10.1016/j.tetlet.2005.10.090, PII S0040403905023233
    • Gracias V, Darczak D, Gasiecki AF, Djuric SW (2005) Synthesis of fused triazolo-imidazole derivatives by sequential van Leusen/alkyne-azide cycloaddition reactions. Tetrahedron Lett 46:9053-9056. doi:10.1016/j.tetlet. 2005.10.090 (Pubitemid 41711875)
    • (2005) Tetrahedron Letters , vol.46 , Issue.52 , pp. 9053-9056
    • Gracias, V.1    Darczak, D.2    Gasiecki, A.F.3    Djuric, S.W.4
  • 19
    • 33645869286 scopus 로고    scopus 로고
    • Cu(I)-catalyzed onepot synthesis of 1,4-disubstituted 1,2,3-triazoles via nucleophilic displacement and 1,3-dipolar cycloaddition
    • doi:10.1016/j.tetlet.2006.03.007
    • Sreedhar B, Reddy PS, Kumar NS (2006) Cu(I)-catalyzed onepot synthesis of 1,4-disubstituted 1,2,3-triazoles via nucleophilic displacement and 1,3-dipolar cycloaddition. Tetrahedron Lett 47:3055-3058. doi:10.1016/j.tetlet.2006.03.007
    • (2006) Tetrahedron Lett , vol.47 , pp. 3055-3058
    • Sreedhar, B.1    Reddy, P.S.2    Kumar, N.S.3
  • 20
    • 33645866173 scopus 로고    scopus 로고
    • Three-component coupling of alkynes Baylis-Hillman adducts and sodium azide: A new synthesis of substituted triazoles
    • doi:10.1016/j.tetlet.2006.03.037
    • Chandrasekhar S, Basu D, Rambabu C (2006) Three-component coupling of alkynes, Baylis-Hillman adducts and sodium azide: a new synthesis of substituted triazoles. Tetrahedron Lett 47:3059-3063. doi:10.1016/j.tetlet.2006.03.037
    • (2006) Tetrahedron Lett , vol.47 , pp. 3059-3063
    • Chandrasekhar, S.1    Basu, D.2    Rambabu, C.3
  • 21
    • 9344238756 scopus 로고    scopus 로고
    • Combining biginelli multicomponent and click chemistry: Generation of 6-(1,2,3-triazol-1-yl)-dihydropyrimidone libraries
    • DOI 10.1021/cc0498938
    • Khanetskyy B, Dallinger D, Kappe CO (2004) Combining biginelli multicomponent and click chemistry: generation of 6-(1,2,3-triazol-1-yl)- dihydropyrimidone libraries. J Comb Chem 6:884-892. doi:10.1021/cc0498938 (Pubitemid 39556558)
    • (2004) Journal of Combinatorial Chemistry , vol.6 , Issue.6 , pp. 884-892
    • Khanetskyy, B.1    Dallinger, D.2    Kappe, C.O.3
  • 22
    • 33847753903 scopus 로고    scopus 로고
    • Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenyl moiety and evaluation of their antibacterial and antifungal activities
    • DOI 10.1016/j.ejmech.2006.09.003, PII S0223523406003217
    • Ashok M, Holla BS, Kumari NS (2007) Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenylmoiety and evaluation of their antibacterial and antifungal activities. Eur J Med Chem 42:380-385. doi:10.1016/j.ejmech.2006.09.003 (Pubitemid 46371285)
    • (2007) European Journal of Medicinal Chemistry , vol.42 , Issue.3 , pp. 380-385
    • Ashok, M.1    Holla, B.S.2    Kumari, N.S.3
  • 23
    • 0001457151 scopus 로고
    • Two new synthetic substances active against viruses of the psittacosis-lymphogranuloma-trachoma group
    • Hurst EW, Hull R (1961) Two new synthetic substances active against viruses of the psittacosis-lymphogranuloma-trachoma group. J Med Pharm Chem 3:215-229
    • (1961) J Med Pharm Chem , vol.3 , pp. 215-229
    • Hurst, E.W.1    Hull, R.2
  • 24
    • 1542404601 scopus 로고    scopus 로고
    • Synthesis and anti-inflammatory activity of some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetic acid derivatives
    • DOI 10.1016/j.bmcl.2004.01.039, PII S0960894X04001180
    • Bahekar SS, Shinde DB (2004) Synthesis and anti-inflammatory activity of some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydro- pyrimidin-5-yl]- acetic acid derivatives.BioorgMed Chem Lett 14:1733-1736. doi:10.1016/j.bmcl. 2004.01.039 (Pubitemid 38340676)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.7 , pp. 1733-1736
    • Bahekar, S.S.1    Shinde, D.B.2
  • 26
    • 0034519777 scopus 로고    scopus 로고
    • Biologically active dihydropyrimidones of the Biginelli-type - A literature survey
    • DOI 10.1016/S0223-5234(00)01189-2
    • Kappe CO (2000) Biologically active dihydropyrimidones of the Biginelli-type-a literature survey. Eur J Med Chem 35:1043-1052. doi:10.1016/S0223-5234(00)01189-2 (Pubitemid 32050011)
    • (2000) European Journal of Medicinal Chemistry , vol.35 , Issue.12 , pp. 1043-1052
    • Kappe, C.O.1
  • 28
    • 77956550101 scopus 로고    scopus 로고
    • Synthesis of diheterocyclic compounds based on triazolyl methoxy phenylquinazolines via a one-pot four-component-click reaction
    • doi:10.1021/cc100043z
    • Dabiri M, Salehi P, Bahramnejad M, Sherafat F (2010) Synthesis of diheterocyclic compounds based on triazolyl methoxy phenylquinazolines via a one-pot four-component-click reaction. J Comb Chem 12:638-642. doi:10.1021/cc100043z
    • (2010) J Comb Chem , vol.12 , pp. 638-642
    • Dabiri, M.1    Salehi, P.2    Bahramnejad, M.3    Sherafat, F.4
  • 29
    • 0037474675 scopus 로고    scopus 로고
    • Silica sulfuric acid: An efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
    • DOI 10.1016/S0040-4039(03)00436-2
    • Salehi P, Dabiri M, Zolfigol MA, Bodaghi Fard MA (2003) Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett 44:2889-2891. doi:10.1016/S0040-4039(03)00436-2 (Pubitemid 36324402)
    • (2003) Tetrahedron Letters , vol.44 , Issue.14 , pp. 2889-2891
    • Salehi, P.1    Dabiri, M.2    Zolfigol, M.A.3    Bodaghi Fard, M.A.4
  • 30
    • 0142027268 scopus 로고    scopus 로고
    • Efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones over silica sulfuric acid as a reusable catalyst under solvent-free conditions
    • doi:10.3987/COM-03-9837
    • Salehi P, Dabiri M, Zolfigol MA, Bodaghi Fard MA (2003) Efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones over silica sulfuric acid as a reusable catalyst under solvent-free conditions. Heterocycles 60:2435-2440. doi:10.3987/COM-03-9837
    • (2003) Heterocycles , vol.60 , pp. 2435-2440
    • Salehi, P.1    Dabiri, M.2    Zolfigol, M.A.3    Fard Ma, B.4
  • 31
    • 24044531286 scopus 로고    scopus 로고
    • Organic azides: An exploding diversity of a unique class of compounds
    • DOI 10.1002/anie.200400657
    • Bräse S,Gil C, KnepperK, ZimmermannV (2005) Organic azides: an exploding diversity of a unique class of compounds. Angew Chem Int Ed 44:5188-5240. doi:10.1002/anie.200400657 (Pubitemid 41223873)
    • (2005) Angewandte Chemie - International Edition , vol.44 , Issue.33 , pp. 5188-5240
    • Brase, S.1    Gil, C.2    Knepper, K.3    Zimmermann, V.4
  • 32
    • 33845278154 scopus 로고
    • Azides: Their preparation and synthetic uses
    • doi:10.1021/cr00084a001
    • Scriven EFV, TurnbullK (1988) Azides: their preparation and synthetic uses. Chem Rev 88:297-368. doi:10.1021/cr00084a001
    • (1988) Chem Rev , vol.88 , pp. 297-368
    • Efv Turnbullk, S.1
  • 34
    • 84957140237 scopus 로고
    • 1 Prop-2-ynyl ethers
    • doi:10.1070/RC1980v049n09ABEH002512
    • Karaev SF, Garaeva ShV (1980) 1. Prop-2-ynyl ethers. Russ Chem Rev 49:865-879. doi:10.1070/RC1980v049n09ABEH002512
    • (1980) Russ Chem Rev , vol.49 , pp. 865-879
    • Karaev, S.F.1    Shv, G.2
  • 35
    • 0038188697 scopus 로고    scopus 로고
    • Synthesis of meso-substituted porphyrins carrying carboranes and oligo(ethylene glycol) units for potential applications in boron neutron capture therapy
    • doi:10.1039/b209534c
    • Frixa C, Mahon MF, Thompson AS, Threadgill MD (2003) Synthesis of meso-substituted porphyrins carrying carboranes and oligo(ethylene glycol) units for potential applications in boron neutron capture therapy. Org Biomol Chem 1:306-317. doi:10.1039/b209534c
    • (2003) Org Biomol Chem , vol.1 , pp. 306-317
    • Frixa, C.1    Mahon, M.F.2    Thompson, A.S.3    Threadgill, M.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.