메뉴 건너뛰기




Volumn 15, Issue 6, 2013, Pages 291-297

Multicomponent solvent-free synthesis of benzimidazolyl imidazo[1,2-a]-pyridine under microwave irradiation

Author keywords

benzimidazole imidazo 1,2 a pyridines; bis heterocyclic skeletons; microwave irradiation; solvent free; three component reaction

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; IMIDAZOLE DERIVATIVE; MESYLIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; SCANDIUM; SCANDIUM TRIFLATE;

EID: 84878856661     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co400010y     Document Type: Article
Times cited : (80)

References (42)
  • 1
    • 57749188299 scopus 로고    scopus 로고
    • Targeting cancer with small molecule kinase inhibitors
    • Zhang, J.; Yang, P. L.; Gray, N. S. Targeting cancer with small molecule kinase inhibitors Nat. Rev. Cancer 2009, 9, 28-39
    • (2009) Nat. Rev. Cancer , vol.9 , pp. 28-39
    • Zhang, J.1    Yang, P.L.2    Gray, N.S.3
  • 3
    • 65249100749 scopus 로고    scopus 로고
    • Strategies for innovation in multicomponent reaction design
    • Ganem, B. Strategies for innovation in multicomponent reaction design Acc. Chem. Res. 2009, 42, 463-472
    • (2009) Acc. Chem. Res. , vol.42 , pp. 463-472
    • Ganem, B.1
  • 4
    • 77956524122 scopus 로고    scopus 로고
    • Multicomponent reactions for the synthesis of pyrroles
    • Estévez, V.; Villacampa, M.; Menéndez, J. C. Multicomponent reactions for the synthesis of pyrroles Chem. Soc. Rev. 2010, 39, 4402-4421
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 4402-4421
    • Estévez, V.1    Villacampa, M.2    Menéndez, J.C.3
  • 5
  • 6
    • 79959791080 scopus 로고    scopus 로고
    • Imides: Forgotten players in the Ugi reaction. One-pot multicomponent synthesis of quinazolinones
    • Mossetti, R.; Pirali, T.; Saggiorato, D.; Tron, G. C. Imides: Forgotten players in the Ugi reaction. One-pot multicomponent synthesis of quinazolinones Chem. Commun. 2011, 47, 6966-6968
    • (2011) Chem. Commun. , vol.47 , pp. 6966-6968
    • Mossetti, R.1    Pirali, T.2    Saggiorato, D.3    Tron, G.C.4
  • 7
    • 84856155925 scopus 로고    scopus 로고
    • Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction
    • Cerulli, V.; Banfi, L.; Basso, A.; Rocca, V.; Riva, R. Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction Org. Biomol. Chem. 2012, 10, 1255-1274
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 1255-1274
    • Cerulli, V.1    Banfi, L.2    Basso, A.3    Rocca, V.4    Riva, R.5
  • 8
    • 34548528526 scopus 로고    scopus 로고
    • New entry to convertible isocyanides for the Ugi reaction and its application to the stereocontrolled formal total synthesis of the proteasome inhibitor omuralide
    • Gilley, C. B.; Buller, M. J.; Kobayashi, Y. New entry to convertible isocyanides for the Ugi reaction and its application to the stereocontrolled formal total synthesis of the proteasome inhibitor omuralide Org. Lett. 2007, 9, 3631-3634
    • (2007) Org. Lett. , vol.9 , pp. 3631-3634
    • Gilley, C.B.1    Buller, M.J.2    Kobayashi, Y.3
  • 9
    • 84856683089 scopus 로고    scopus 로고
    • Challenging 50 years of established views on Ugi reaction: A theoretical approach
    • Chéron, N.; Ramozzi, R.; Kaïm, L. E.; Grimaud, L.; Fleurat-Lessard, P. Challenging 50 years of established views on Ugi reaction: A theoretical approach J. Org. Chem. 2012, 77, 1361-1366
    • (2012) J. Org. Chem. , vol.77 , pp. 1361-1366
    • Chéron, N.1    Ramozzi, R.2    Kaïm, L.E.3    Grimaud, L.4    Fleurat-Lessard, P.5
  • 10
    • 34250818052 scopus 로고    scopus 로고
    • A general and efficient five-step one-pot procedure leading to nitrogen-bridgehead heterocycles containing an imidazole ring
    • Parenty, A. D. C.; Song, Y. F.; Richmond, C. J.; Cronin, L. A general and efficient five-step one-pot procedure leading to nitrogen-bridgehead heterocycles containing an imidazole ring Org. Lett. 2007, 9, 2253-2256
    • (2007) Org. Lett. , vol.9 , pp. 2253-2256
    • Parenty, A.D.C.1    Song, Y.F.2    Richmond, C.J.3    Cronin, L.4
  • 11
    • 36649030371 scopus 로고    scopus 로고
    • Diversification of the three-component coupling of 2-aminoheterocycles, aldehydes, and isonitriles: Efficient parallel synthesis of a diverse and druglike library of imidazo- and tetrahydroimidazo[1,2- a ] heterocycles
    • Kercher, T.; Rao, C.; Bencsik, J. R.; Josey, J. A. Diversification of the three-component coupling of 2-aminoheterocycles, aldehydes, and isonitriles: Efficient parallel synthesis of a diverse and druglike library of imidazo- and tetrahydroimidazo[1,2- a ] heterocycles J. Comb. Chem. 2007, 9, 1177-1187
    • (2007) J. Comb. Chem. , vol.9 , pp. 1177-1187
    • Kercher, T.1    Rao, C.2    Bencsik, J.R.3    Josey, J.A.4
  • 12
    • 80455173672 scopus 로고    scopus 로고
    • Systematic structure modifications of imidazo[1,2- a ]pyrimidine to reduce metabolism mediated by aldehyde oxidase (AO)
    • Linton, A.; Kang, P.; Ornelas, M.; Kephart, S.; Hu, Q.; Pairish, M.; Jiang, Y.; Guo, C. Systematic structure modifications of imidazo[1,2- a ]pyrimidine to reduce metabolism mediated by aldehyde oxidase (AO) J. Med. Chem. 2011, 54, 7705-7712
    • (2011) J. Med. Chem. , vol.54 , pp. 7705-7712
    • Linton, A.1    Kang, P.2    Ornelas, M.3    Kephart, S.4    Hu, Q.5    Pairish, M.6    Jiang, Y.7    Guo, C.8
  • 13
    • 0141676272 scopus 로고    scopus 로고
    • Improvement of cerebral blood flow by olprinone, a phosphodiesterase-3 inhibitor, in mild heart failure
    • Ueda, T.; Mizusgige, K.; Yukiiri, K.; Takahashi, T.; Kohno, M. Improvement of cerebral blood flow by olprinone, a phosphodiesterase-3 inhibitor, in mild heart failure Cerebrovasc. Dis. 2003, 16, 396-401
    • (2003) Cerebrovasc. Dis. , vol.16 , pp. 396-401
    • Ueda, T.1    Mizusgige, K.2    Yukiiri, K.3    Takahashi, T.4    Kohno, M.5
  • 14
    • 12944331138 scopus 로고    scopus 로고
    • Zolpidem: A review of its use in the management of insomnia
    • Harrison, T. S.; Keating, G. M. Zolpidem: A review of its use in the management of insomnia CNS Drugs 2005, 19, 65-89
    • (2005) CNS Drugs , vol.19 , pp. 65-89
    • Harrison, T.S.1    Keating, G.M.2
  • 15
    • 34848907405 scopus 로고    scopus 로고
    • Synthesis of polysubstituted imidazo[1,2- a ]pyridines via microwave-assisted one-pot cyclization/Suzuki coupling/palladium-catalyzed heteroarylation
    • Koubachi, J.; Kazzouli, S. E.; Berteina-Raboin, S.; Mouaddib, A.; Guillaumet, G. Synthesis of polysubstituted imidazo[1,2- a ]pyridines via microwave-assisted one-pot cyclization/Suzuki coupling/palladium-catalyzed heteroarylation J. Org. Chem. 2007, 72, 7650-7655
    • (2007) J. Org. Chem. , vol.72 , pp. 7650-7655
    • Koubachi, J.1    Kazzouli, S.E.2    Berteina-Raboin, S.3    Mouaddib, A.4    Guillaumet, G.5
  • 16
    • 74049159507 scopus 로고    scopus 로고
    • Novel one-pot three-component reaction for the synthesis of [2-(alkylsulfanyl)imidazo[1,2- a ]pyridin-3-yl](aryl)methanone
    • Kianmehr, E.; Ghanbari, M.; Niri, M. N.; Faramarzi, R. Novel one-pot three-component reaction for the synthesis of [2-(alkylsulfanyl)imidazo[1,2- a ]pyridin-3-yl](aryl)methanone J. Comb. Chem. 2010, 12, 41-44
    • (2010) J. Comb. Chem. , vol.12 , pp. 41-44
    • Kianmehr, E.1    Ghanbari, M.2    Niri, M.N.3    Faramarzi, R.4
  • 19
    • 77953790002 scopus 로고    scopus 로고
    • Inhibition of protein kinase C-driven nuclear factor-KB activation: Synthesis, structure-activity relationship, and pharmacological profiling of pathway specific benzimidazole probe molecules
    • Peddibhotla, S.; Shi, R.; Khan, P.; Smith, L. H.; Mangravita-Novo, A.; Vicchiarelli, M.; Su, Y.; Okolotowicz, K. J.; Cashman, J. R.; Reed, J. C.; Roth, G. P. Inhibition of protein kinase C-driven nuclear factor-KB activation: Synthesis, structure-activity relationship, and pharmacological profiling of pathway specific benzimidazole probe molecules J. Med. Chem. 2010, 53, 4793-4797
    • (2010) J. Med. Chem. , vol.53 , pp. 4793-4797
    • Peddibhotla, S.1    Shi, R.2    Khan, P.3    Smith, L.H.4    Mangravita-Novo, A.5    Vicchiarelli, M.6    Su, Y.7    Okolotowicz, K.J.8    Cashman, J.R.9    Reed, J.C.10    Roth, G.P.11
  • 21
    • 57549102834 scopus 로고    scopus 로고
    • Combinatorial libraries of bis-heterocyclic compounds with skeletal diversity
    • Soural, M.; Bouillon, I.; Krchňák, V. Combinatorial libraries of bis-heterocyclic compounds with skeletal diversity J. Comb. Chem. 2008, 10, 923-933
    • (2008) J. Comb. Chem. , vol.10 , pp. 923-933
    • Soural, M.1    Bouillon, I.2    Krchňák, V.3
  • 22
    • 41949118427 scopus 로고    scopus 로고
    • CH functionalization/CN bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    • Brasche, G.; Buchwald, S. L. CH functionalization/CN bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines Angew. Chem., Int. Ed. 2008, 47, 1932-1934
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1932-1934
    • Brasche, G.1    Buchwald, S.L.2
  • 23
    • 78651504130 scopus 로고    scopus 로고
    • Copper-catalyzed intramolecular C-N bond formation: A straightforward synthesis of benzimidazole derivatives in water
    • Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. Copper-catalyzed intramolecular C-N bond formation: A straightforward synthesis of benzimidazole derivatives in water J. Org. Chem. 2011, 76, 716-719
    • (2011) J. Org. Chem. , vol.76 , pp. 716-719
    • Peng, J.1    Ye, M.2    Zong, C.3    Hu, F.4    Feng, L.5    Wang, X.6    Wang, Y.7    Chen, C.8
  • 24
    • 75749106169 scopus 로고    scopus 로고
    • Fully automated continuous flow synthesis of highly functionalized imidazo[1,2- a ] heterocycles
    • Herath, A.; Dahl, R.; Cosford, N. D. P. Fully automated continuous flow synthesis of highly functionalized imidazo[1,2- a ] heterocycles Org. Lett. 2010, 12, 412-415
    • (2010) Org. Lett. , vol.12 , pp. 412-415
    • Herath, A.1    Dahl, R.2    Cosford, N.D.P.3
  • 25
    • 79959890092 scopus 로고    scopus 로고
    • Combinatorial discovery of fluorescent pharmacophores by multicomponent reactions in droplet arrays
    • Burchak, O. N.; Mugherli, L.; Ostuni, M.; Lacapère, J. J.; Maxim, Y.; Balakirev, M. Y. Combinatorial discovery of fluorescent pharmacophores by multicomponent reactions in droplet arrays J. Am. Chem. Soc. 2011, 133, 10058-10061
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 10058-10061
    • Burchak, O.N.1    Mugherli, L.2    Ostuni, M.3    Lacapère, J.J.4    Maxim, Y.5    Balakirev, M.Y.6
  • 26
    • 79955576570 scopus 로고    scopus 로고
    • Base-promoted cyclization of N -propargylaminopyridines. Synthesis of imidazo[1,2-a]pyridine derivatives
    • Husinec, S.; Markovic, R.; Petkovic, M.; Nasufovic, V.; Savic, V. A. Base-promoted cyclization of N -propargylaminopyridines. Synthesis of imidazo[1,2-a]pyridine derivatives Org. Lett. 2011, 13, 2286-2289
    • (2011) Org. Lett. , vol.13 , pp. 2286-2289
    • Husinec, S.1    Markovic, R.2    Petkovic, M.3    Nasufovic, V.4    Savic, V.A.5
  • 27
    • 33645231449 scopus 로고    scopus 로고
    • Sequential Ugi/Strecker reactions via microwave assisted organic synthesis: Novel 3-center-4-component and 3-center-5-component multicomponent reactions
    • Schwerkoske, J.; Masquelin, T.; Perunb, T.; Hulmea, C. Sequential Ugi/Strecker reactions via microwave assisted organic synthesis: novel 3-center-4-component and 3-center-5-component multicomponent reactions Tetrahedron Lett. 2006, 47, 2989-2991
    • (2006) Tetrahedron Lett. , vol.47 , pp. 2989-2991
    • Schwerkoske, J.1    Masquelin, T.2    Perunb, T.3    Hulmea, C.4
  • 28
    • 33846900673 scopus 로고    scopus 로고
    • Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot
    • DiMauro, E. F.; Kennedy, J. M. Rapid synthesis of 3-amino- imidazopyridines by a microwave-assisted four-component coupling in one pot J. Org. Chem. 2007, 72, 1013-1016
    • (2007) J. Org. Chem. , vol.72 , pp. 1013-1016
    • Dimauro, E.F.1    Kennedy, J.M.2
  • 29
    • 0042175801 scopus 로고    scopus 로고
    • Solid-phase synthesis of imidazo[1,2- a ]pyridine using sodium benzenesulfinate as a traceless linker
    • Chen, Y.; Lam, Y.; Lai, Y. H. Solid-phase synthesis of imidazo[1,2- a ]pyridine using sodium benzenesulfinate as a traceless linker Org. Lett. 2002, 4, 3935-3937
    • (2002) Org. Lett. , vol.4 , pp. 3935-3937
    • Chen, Y.1    Lam, Y.2    Lai, Y.H.3
  • 30
    • 34047238367 scopus 로고    scopus 로고
    • Efficient solid-phase synthesis of a library of imidazo[1,2- a ]pyridine-8-carboxamides
    • Kamal, A.; Devaiah, V.; Reddy, K. L.; Shetti, R. V. C. R. N. C.; Shankaraiah, N. Efficient solid-phase synthesis of a library of imidazo[1,2- a ]pyridine-8-carboxamides J. Comb. Chem. 2007, 9, 267-274
    • (2007) J. Comb. Chem. , vol.9 , pp. 267-274
    • Kamal, A.1    Devaiah, V.2    Reddy, K.L.3    Shetti, R.V.C.R.N.C.4    Shankaraiah, N.5
  • 32
    • 84857200759 scopus 로고    scopus 로고
    • Cu(I)-catalyzed synthesis of imidazo[1,2- a ]pyridines from aminopyridines and nitroolefins using air as the oxidant
    • Yan, R. L.; Yan, H.; Ma, C.; Ren, Z. Y.; Gao, X. A.; Huang, G. S.; Liang, Y. M. Cu(I)-catalyzed synthesis of imidazo[1,2- a ]pyridines from aminopyridines and nitroolefins using air as the oxidant J. Org. Chem. 2012, 77, 2024-2028
    • (2012) J. Org. Chem. , vol.77 , pp. 2024-2028
    • Yan, R.L.1    Yan, H.2    Ma, C.3    Ren, Z.Y.4    Gao, X.A.5    Huang, G.S.6    Liang, Y.M.7
  • 33
    • 70350686744 scopus 로고    scopus 로고
    • Traceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media
    • Maiti, B.; Chanda, K.; Sun, C. M. Traceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media Org. Lett. 2009, 11, 4826-4829
    • (2009) Org. Lett. , vol.11 , pp. 4826-4829
    • Maiti, B.1    Chanda, K.2    Sun, C.M.3
  • 34
    • 78649676888 scopus 로고    scopus 로고
    • Novel cyclization of bis-Boc-guanidines: Expeditive traceless synthesis of 1,3,5-oxadiazinones under microwave conditions
    • Yellol, G. S.; Tsai, W. C.; Sun, C. M. Novel cyclization of bis-Boc-guanidines: Expeditive traceless synthesis of 1,3,5-oxadiazinones under microwave conditions Chem. Commun. 2010, 46, 9170-9172
    • (2010) Chem. Commun. , vol.46 , pp. 9170-9172
    • Yellol, G.S.1    Tsai, W.C.2    Sun, C.M.3
  • 35
    • 80054725340 scopus 로고    scopus 로고
    • Base-catalyzed Povarov reaction: An unusual [1,3] sigmatropic rearrangement to dihydropyrimidobenzimidazoles
    • Chen, C. H.; Yellol, G. S.; Lin, P. T.; Sun, C. M. Base-catalyzed Povarov reaction: An unusual [1,3] sigmatropic rearrangement to dihydropyrimidobenzimidazoles Org. Lett. 2011, 13, 5120-5123
    • (2011) Org. Lett. , vol.13 , pp. 5120-5123
    • Chen, C.H.1    Yellol, G.S.2    Lin, P.T.3    Sun, C.M.4
  • 36
    • 45349103379 scopus 로고    scopus 로고
    • Microwave-assisted organic synthesis and transformations using benign reaction media
    • Polshettiwar, V.; Varma, R. S. Microwave-assisted organic synthesis and transformations using benign reaction media Acc. Chem. Res. 2008, 41, 629-639
    • (2008) Acc. Chem. Res. , vol.41 , pp. 629-639
    • Polshettiwar, V.1    Varma, R.S.2
  • 37
    • 79960021245 scopus 로고    scopus 로고
    • Novel approach towards the synthesis of skeletally diverse benzimidazole-pyrrolo[1,2- a ]quinoxaline by SNAr/Pictet-Spengler reaction under focused microwave irradiation
    • Maiti, B.; Sun, C. M. Novel approach towards the synthesis of skeletally diverse benzimidazole-pyrrolo[1,2- a ]quinoxaline by SNAr/Pictet-Spengler reaction under focused microwave irradiation New J. Chem. 2011, 35, 1385-1396
    • (2011) New J. Chem. , vol.35 , pp. 1385-1396
    • Maiti, B.1    Sun, C.M.2
  • 38
    • 84856849438 scopus 로고    scopus 로고
    • Microwave-assisted linear approach toward highly substituted benzo[d]oxazol-5-yl-1 H -benzo[d]imidazole on ionic liquid support
    • Chanda, K.; Maiti, B.; Tseng, C. C.; Sun, C. M. Microwave-assisted linear approach toward highly substituted benzo[d]oxazol-5-yl-1 H -benzo[d]imidazole on ionic liquid support ACS Comb. Sci. 2012, 14, 115-123
    • (2012) ACS Comb. Sci. , vol.14 , pp. 115-123
    • Chanda, K.1    Maiti, B.2    Tseng, C.C.3    Sun, C.M.4
  • 39
    • 26844563013 scopus 로고    scopus 로고
    • Synthesis of imidazo[1,2- a ]annulated pyridines, pyrazines, and pyrimidines by a novel three component condensation
    • Groebke, K.; Weber, L.; Mehlin, F. Synthesis of imidazo[1,2- a ]annulated pyridines, pyrazines, and pyrimidines by a novel three component condensation Synlett. 1998, 29, 661-663
    • (1998) Synlett. , vol.29 , pp. 661-663
    • Groebke, K.1    Weber, L.2    Mehlin, F.3
  • 40
    • 0032575201 scopus 로고    scopus 로고
    • Parallel synthesis of 3-aminoimidazo[1,2- a ]pyridines and pyrazines by a new three-component condensation
    • Blackburn, C.; Guan, B.; Fleming, K.; Shiosaki, K.; Tsai, S. Parallel synthesis of 3-aminoimidazo[1,2- a ]pyridines and pyrazines by a new three-component condensation Tetrahedron Lett. 1998, 39, 3635-3638
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3635-3638
    • Blackburn, C.1    Guan, B.2    Fleming, K.3    Shiosaki, K.4    Tsai, S.5
  • 41
    • 0031661388 scopus 로고    scopus 로고
    • A new heterocyclic multicomponent reaction for the combinatorial synthesis of fused 3-aminoimidazoles
    • Bienayme, H.; Bouzid, K. A new heterocyclic multicomponent reaction for the combinatorial synthesis of fused 3-aminoimidazoles Angew. Chem., Int. Ed. 1998, 37, 2234-2237
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2234-2237
    • Bienayme, H.1    Bouzid, K.2
  • 42
    • 84878851536 scopus 로고    scopus 로고
    • 3 Formula weight: 555.64. Crystal system: Monoclinic. The crystal data has been deposited at Cambridge Crystallographic Data Centre [CCDC No. 859133]. Copies of the data can be obtained free of charge via or CCDC, 12 union Road, 50 Cambridge CB2 1EZ, U.K.
    • 3. Formula weight: 555.64. Crystal system: Monoclinic. The crystal data has been deposited at Cambridge Crystallographic Data Centre [CCDC No. 859133]. Copies of the data can be obtained free of charge via www.ccdc.ac.uk/conts/retrieving.html or CCDC, 12 union Road, 50 Cambridge CB2 1EZ, U.K.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.