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Volumn 16, Issue 1, 2012, Pages 145-150

Three-component reactions of isocyanides, dialkyl acetylenedicarboxylates, and trans-cinnamoyl chlorides for the synthesis of highly functionalized 2-vinyl furans

Author keywords

2 vinyl furan; Alkyl isocyanide; Dialkyl acetylenedicarboxylate; Furan synthesis; MCR; Multi component cyclization; Trans cinnamoyl chloride

Indexed keywords

AMPHOLYTE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; DIETHYL 2 (2 CHLORO 2 PHENYLVINYL) 5 (CYCLOHEXYLAMINO)FURAN 3,4 DICARBOXYLATE; DIETHYL 2 (2 CHLORO 2 PHENYLVINYL) 5 (TERT BUTYL AMINO)FURAN 3,4 DICARBOXYLATE; DIETHYL 2 (2 CHLORO 2 PHENYLVINYL) 5 (TERT BUTYLAMINO)FURAN 3,4 DICARBOXYLATE; DIETHYL 2 (2 CHLORO 2 PHENYLVINYL) 5 [(1,1,3,3 TETRAMETHYLBUTYL)AMINO]FURAN 3,4 DICARBOXYLATE; DIETHYL 2 [2 CHLORO 2 (4 METHYLPHENYL)VINYL] 5 (TERT BUTYLAMINO)FURAN 3,4 DICARBOXYLATE; DIMETHYL 2 (2 CHLORO 2 PHENYLVINYL) 5 (CYCLOHEXYLAMINO)FURAN 3,4 DICARBOXYLATE; DIMETHYL 2 (2 CHLORO 2 PHENYLVINYL) 5 [(1,1,3,3 TETRAMETHYLBUTYL)AMINO]FURAN 3,4 DICARBOXYLATE; DIMETHYL 2 [2 CHLORO 2 (4 METHOXYPHENYL)VINYL] 5 [(1,1,3,3 TETRAMETHYLBUTYL)AMINO]FURAN 3,4 DICARBOXYLATE; DIMETHYL 2 [2 CHLORO 2 (4 METHYLPHENYL)VINYL) 5 (CYCLOHEXYLAMINO)FURAN 3,4 DICARBOXYLATE; DIMETHYL 2 [2 CHLORO 2 (4 METHYLPHENYL)VINYL) 5 (TERT BUTYLAMINO)FURAN 3,4 DICARBOXYLATE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84858702716     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9341-2     Document Type: Article
Times cited : (7)

References (36)
  • 1
    • 0022406615 scopus 로고
    • Kallolide A, a new antiinflammatory diterpenoid, and related lactones from the Caribbean octocoral Pseudopterogorgia kallos (Bielschowsky)
    • DOI 10.1021/jo00350a061
    • Kallolide A, Look SA, Burch MT, Fenical W, Qi-tai Z, Clardy J (1985) A New antiinflammatory diterpenoid, and related lactones from the caribbean octocoral pseudopterogorgia kallos. J Org Chem 50: 5741-5746. doi:10.1021/jo00350a061 (Pubitemid 16170790)
    • (1985) Journal of Organic Chemistry , vol.50 , Issue.26 , pp. 5741-5746
    • Look, S.A.1    Burch, M.T.2    Fenical, W.3
  • 2
    • 0019413999 scopus 로고
    • Lophotoxin: A novel neuromuscular toxin from Pacific sea whips of the genus Lophogorgia
    • Fenical W, Okeeda RK, Basnadurraga MM, Culver P, Jacobs RS (1981) Lophotoxin: a novel neuromuscular toxin from pacific sea whips of the genus Lophogorgia. Science 212: 1512-1514. doi:10.1126/science.6112796 (Pubitemid 11063022)
    • (1981) Science , vol.212 , Issue.4502 , pp. 1512-1514
    • Fenical, W.1    Okuda, R.K.2    Bandurraga, M.M.3
  • 3
    • 0000119097 scopus 로고
    • Synthesis of optically active pheromones
    • doi:10.1016/S0040-4020(01)81007-3
    • Mori K (1989) Synthesis of optically active pheromones. Tetrahedron 45: 3233-3298. doi:10.1016/S0040-4020(01)81007-3
    • (1989) Tetrahedron , vol.45 , pp. 3233-3298
    • Mori, K.1
  • 4
    • 0000338761 scopus 로고
    • Furans and their benzo derivatives
    • Katrizky AR, Rees CW (eds) Pergamon, New York
    • Sargent MV, Dean FM (1984) Furans and their benzo derivatives. In: Katrizky AR, Rees CW (eds) Comprehensive heterocyclic chemistry. Pergamon, New York
    • (1984) Comprehensive Heterocyclic Chemistry
    • Sargent, M.V.1    Dean, F.M.2
  • 6
    • 0003607021 scopus 로고
    • Five-membered rings with two heteroatoms, each with their fused carbocyclic derivatives
    • Katritzky AR, Rees CW (eds) Pergamon, New York
    • DonnellyDMX,MeeganMJ(1984) Five-membered rings with two heteroatoms, each with their fused carbocyclic derivatives. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry, vol 4. Pergamon, New York
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4
    • Donnelly, D.M.X.1    Meegan, M.J.2
  • 10
    • 0001648131 scopus 로고
    • Two furanosesquiterpene marine metabolites with antifeedant properties
    • doi:10.1002/hlca.19800630805
    • Schulte G, Schener PJ, McConnel O (1980) Two furanosesquiterpene marine metabolites with antifeedant properties. Helv Chim Acta 63: 2159-2167. doi:10.1002/hlca.19800630805
    • (1980) Helv Chim Acta , vol.63 , pp. 2159-2167
    • Schulte, G.1    Schener, P.J.2    McConnel, O.3
  • 11
    • 0030142811 scopus 로고    scopus 로고
    • Acid-catalyzed polycondensation of furfuryl alcohol:Mechanisms of chromophore formation and cross-linking
    • doi:10. 1021/ma951522f
    • ChouraM, Belgacem NM,GandiniA (1996) Acid-catalyzed polycondensation of furfuryl alcohol:mechanisms of chromophore formation and cross-linking. Macromolecules 29: 3839-3850. doi:10. 1021/ma951522f
    • (1996) Macromolecules , vol.29 , pp. 3839-3850
    • Choura, M.1    Belgacem, N.M.2    Gandini, A.3
  • 14
    • 43849104916 scopus 로고    scopus 로고
    • Palladium-catalyzed direct oxidative vinylation of thiophenes and furans under weakly basic conditions
    • doi:10.1016/j.tet.2008.01.058
    • Maehara A, Satoh T, Miura M (2008) Palladium-catalyzed direct oxidative vinylation of thiophenes and furans under weakly basic conditions. Tetrahedron 64: 5982-5986. doi:10.1016/j.tet.2008.01.058
    • (2008) Tetrahedron , vol.64 , pp. 5982-5986
    • Maehara, A.1    Satoh, T.2    Miura, M.3
  • 15
    • 70349617692 scopus 로고    scopus 로고
    • Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external- oxidant-free conditions
    • doi:10.1021/ja902762a
    • Wu J, Cui X, Chen L, Jiang G, Wu Y (2009) Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external- oxidant-free conditions. J Am Chem Soc 131: 13888-13889. doi:10.1021/ja902762a
    • (2009) J Am Chem Soc , vol.131 , pp. 13888-13889
    • Wu, J.1    Cui, X.2    Chen, L.3    Jiang, G.4    Wu, Y.5
  • 16
    • 0001750571 scopus 로고
    • Palladium- catalyzed alkenylation of aromatic heterocycles with olefins. Synthesis of functionalized aromatic heterocycles
    • doi:10.1021/jo00318a005
    • Fujiwara Y, Maruyama O, YoshidomiM, Taniguchi H (1981) Palladium- catalyzed alkenylation of aromatic heterocycles with olefins. Synthesis of functionalized aromatic heterocycles. J Org Chem 46: 851-855. doi:10.1021/jo00318a005
    • (1981) J Org Chem , vol.46 , pp. 851-855
    • Fujiwara, Y.1    Maruyama, O.2    Yoshidomi, M.3    Taniguchi, H.4
  • 17
    • 0000185795 scopus 로고    scopus 로고
    • Highly Efficient Pd- Catalyzed Coupling of Arenes with Olefins in the Presence of tert- Butyl Hydroperoxide as Oxidant
    • doi:10.1021/ol991148u
    • Jia C, Lu W, Kitamura T, Fujiwara Y (1999) Highly Efficient Pd- Catalyzed Coupling of Arenes with Olefins in the Presence of tert- Butyl Hydroperoxide as Oxidant. Org Lett 1: 2097-2100. doi:10.1021/ol991148u
    • (1999) Org Lett , vol.1 , pp. 2097-2100
    • Jia, C.1    Lu, W.2    Kitamura, T.3    Fujiwara, Y.4
  • 18
    • 1242352467 scopus 로고    scopus 로고
    • 2-catalyzed Oxidative coupling reaction of benzenes with olefins in the presence of molybdovanadophosphoric acid under atmospheric dioxygen and air
    • doi:10.1021/jo035568f
    • 2-catalyzed Oxidative coupling reaction of benzenes with olefins in the presence of molybdovanadophosphoric acid under atmospheric dioxygen and air. J Org Chem 69: 1221-1226. doi:10.1021/jo035568f
    • (2004) J Org Chem , vol.69 , pp. 1221-1226
    • Tani, M.1    Sakaguchi, S.2    Ishii, Y.3
  • 19
    • 77952542304 scopus 로고    scopus 로고
    • Recent advances in multicomponent reactions for diversity-oriented synthesis
    • doi:10.1016/j.cbpa.2010.03.003
    • Biggs-Houck JE, Younai A, Shaw JT (2010) Recent advances in multicomponent reactions for diversity-oriented synthesis. Curr Opin Chem Biol 14: 371-382. doi:10.1016/j.cbpa.2010.03.003
    • (2010) Curr Opin Chem Biol , vol.14 , pp. 371-382
    • Biggs-Houck, J.E.1    Younai, A.2    Shaw, J.T.3
  • 20
    • 79959799404 scopus 로고    scopus 로고
    • Synthesis of heterocycles via multicomponent reactions I
    • doi:10.1007/978-3-642-12675-8
    • Orru R, Ruijter E (2010) Synthesis of heterocycles via multicomponent reactions I. Top Heterocycl Chem 23. doi:10.1007/978-3-642-12675-8
    • (2010) Top Heterocycl Chem , vol.23
    • Orru, R.1    Ruijter, E.2
  • 21
    • 65249100749 scopus 로고    scopus 로고
    • Strategies for innovation inmulticomponent reaction design
    • doi:10.1021/ar800214s
    • GanemB (2009) Strategies for innovation inmulticomponent reaction design. Acc Chem Res 42: 463-472. doi:10.1021/ar800214s
    • (2009) Acc Chem Res , vol.42 , pp. 463-472
    • Ganem, B.1
  • 22
    • 60749120878 scopus 로고    scopus 로고
    • Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds
    • doi:10.1002/chem.200802140
    • Sunderhaus JD, Martin S (2009) Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chemistry 15: 1300-1308. doi:10.1002/chem.200802140
    • (2009) Chemistry , vol.15 , pp. 1300-1308
    • Sunderhaus, J.D.1    Martin, S.2
  • 23
    • 31544434530 scopus 로고    scopus 로고
    • Recent developments in isocyanide-based multicomponent reactions in applied chemistry
    • doi:10.1021/cr0505728
    • Dömling A (2006) Recent developments in isocyanide-based multicomponent reactions in applied chemistry.ChemRev 106: 17-89. doi:10.1021/cr0505728
    • (2006) ChemRev , vol.106 , pp. 17-89
    • Dömling, A.1
  • 24
    • 2542509173 scopus 로고    scopus 로고
    • Multicomponent Reactions with Isocyanides
    • doi:10.1002/1521- 3773(20000915)39:18〈3168
    • Dömling A, Ugi I (2000) Multicomponent Reactions with Isocyanides. Angew Chem Int Ed 39: 3168-3210. doi:10.1002/1521- 3773(20000915)39:18〈3168
    • (2000) Angew Chem Int Ed , vol.39 , pp. 3168-3210
    • Dömling, A.1    Ugi, I.2
  • 25
    • 34249332060 scopus 로고    scopus 로고
    • Organic synthesis in water: Green protocol for the synthesis of 2-amino furan derivatives
    • DOI 10.1016/j.molcata.2007.02.032, PII S1381116907001318
    • Yadav JS, Subba Reddy BV, Shubashree S, Sadashiv K, Krishna Rao D (2007) Organic synthesis in water: Green protocol for the synthesis of 2-amino furan derivatives. J Mol Catal A 272: 128-131. doi:10.1016/j.molcata.2007.02.032 (Pubitemid 46809576)
    • (2007) Journal of Molecular Catalysis A: Chemical , vol.272 , Issue.1-2 , pp. 128-131
    • Yadav, J.S.1    Reddy, B.V.S.2    Shubashree, S.3    Sadashiv, K.4    Rao, D.K.5
  • 26
    • 0036697701 scopus 로고    scopus 로고
    • The reaction of alkyl isocyanides and dialkylacetylene dicarboxylates with phthalic anhydride derivatives: A novel synthesis of γ -spiroiminolactones
    • doi:10.3184/030823402103172383
    • Shaabani A, Teimouri MB, Bijanzadeh H R (2002) The reaction of alkyl isocyanides and dialkylacetylene dicarboxylates with phthalic anhydride derivatives: a novel synthesis of γ -spiroiminolactones. J Chem Res 381(383): 381-383. doi:10.3184/030823402103172383
    • (2002) J Chem Res , vol.381 , Issue.383 , pp. 381-383
    • Shaabani, A.1    Teimouri, M.B.2    Bijanzadeh, H.R.3
  • 27
    • 13244295523 scopus 로고    scopus 로고
    • One-pot, four-component reaction of isocyanides, dimethyl acetylenedicarboxylate, and cyclobutene-1,2-diones: A synthesis of novel spiroheterocycles
    • DOI 10.1016/j.tetlet.2004.12.117, PII S0040403904028400
    • Nair V, Rajeev SM, Ani D, Rema D, Biju AT (2005) One-pot, four-component reaction of isocyanides, dimethyl acetylenedicarboxylate, and cyclobutene-1,2-diones: a synthesis of novel spiroheterocycles. Tetrahedron Lett 46: 1337-1339. doi:10.1016/j.tetlet.2004.12.117 (Pubitemid 40186753)
    • (2005) Tetrahedron Letters , vol.46 , Issue.8 , pp. 1337-1339
    • Nair, V.1    Menon, R.S.2    Deepthi, A.3    Rema, D.B.4    Biju, A.T.5
  • 28
    • 35548988345 scopus 로고    scopus 로고
    • A facile one-pot synthesis of amino furans using trans-cinnamaldehyde in the Presence of nucleophilic isocyanides
    • Asghari S, Qandalee M (2007) A facile one-pot synthesis of amino furans using trans-cinnamaldehyde in the Presence of nucleophilic isocyanides. Acta Chim Slov 54:638-641
    • (2007) Acta Chim Slov , vol.54 , pp. 638-641
    • Asghari, S.1    Qandalee, M.2
  • 29
    • 31444444924 scopus 로고    scopus 로고
    • Reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates in the presence of benzoyl cyanides: One-pot synthesis of highly functionalized iminolactones
    • doi:10.1016/j.tet.2005.11.043
    • Teimouri MB, Shaabani A, Bazhrang R (2004) Reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates in the presence of benzoyl cyanides: one-pot synthesis of highly functionalized iminolactones. Tetrahedron 62: 1845-1848. doi:10.1016/j.tet.2005.11.043
    • (2004) Tetrahedron , vol.62 , pp. 1845-1848
    • Teimouri, M.B.1    Shaabani, A.2    Bazhrang, R.3
  • 30
    • 0034686870 scopus 로고    scopus 로고
    • The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with o- and p-quinones: A novel synthesis of iminolactones
    • PII S004040390001114X
    • Nair V, Vinod AU, Nair JS, Sreekanth AR, Rath NP (2000) The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with o- and p-quinones: a novel synthesis of iminolactones. Tetrahedron Lett 41: 6675-6679. doi:10.1016/S0040-4039(00)01114-X (Pubitemid 30644896)
    • (2000) Tetrahedron Letters , vol.41 , Issue.34 , pp. 6675-6679
    • Nair, V.1    Vinod, A.U.2    Nair, J.S.3    Sreekanth, A.R.4    Rath, N.P.5
  • 31
    • 5144220811 scopus 로고    scopus 로고
    • A novel pseudo four-component reaction: Unexpected formation of densely functionalized pyrroles
    • DOI 10.1016/j.tetlet.2004.09.039, PII S0040403904019823
    • Shaabani A, Teimouri MB, Arab-Ameri S (2004) A novel pseudo four-component reaction: unexpected formation of densely functionalized pyrroles. Tetrahedron Lett 45: 8409-8413. doi:10.1016/j.tetlet.2004.09.039 (Pubitemid 39345536)
    • (2004) Tetrahedron Letters , vol.45 , Issue.45 , pp. 8409-8413
    • Shaabani, A.1    Teimouri, M.B.2    Arab-Ameri, S.3
  • 32
    • 42749088760 scopus 로고    scopus 로고
    • Reaction of benzoyl chlorides with Huisgen's zwitterion: Synthesis of functionalized 2,5-dihydro-1H-pyrroles and tetra-substituted furans
    • doi:10.1016/j.tet.2008.03.044
    • Yavari I, Mokhtarporyani-Sanandaj A, Moradi L, Mirzaei A (2008) Reaction of benzoyl chlorides with Huisgen's zwitterion: synthesis of functionalized 2,5-dihydro-1H-pyrroles and tetra-substituted furans. Tetrahedron 64: 5221-5225. doi:10.1016/j.tet.2008.03.044
    • (2008) Tetrahedron , vol.64 , pp. 5221-5225
    • Yavari, I.1    Mokhtarporyani-Sanandaj, A.2    Moradi, L.3    Mirzaei, A.4
  • 33
    • 0038045268 scopus 로고    scopus 로고
    • Reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates in the presence of N-alkyl isatins: Convenient synthesis of γ-spiro- iminolactones
    • DOI 10.1016/S0040-4020(03)00809-3
    • Esmaeili AA, Darbanian M (2003) Reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates in the presence of N-alkyl isatins: convenient synthesis of γ -spiro-iminolactones. Tetrahedron 59: 5545-5548. doi:10.1016/S0040-4020(03)00809-3 (Pubitemid 36792226)
    • (2003) Tetrahedron , vol.59 , Issue.29 , pp. 5545-5548
    • Esmaeili, A.A.1    Darbanian, M.2
  • 34
    • 19344365988 scopus 로고    scopus 로고
    • Three-component reactions involving zwitterionic intermediates for the construction of heterocyclic systems: One pot synthesis of highly functionalized γ-iminolactones
    • DOI 10.1016/j.tet.2005.02.053, PII S0040402005003406
    • Esmaeili AA, Zendegani H (2005) Three-component reactions involving zwitterionic intermediates for the construction of heterocyclic systems: one pot synthesis of highly functionalized γ -iminolactones. Tetrahedron 61: 4031-4034. doi:10.1016/j.tet.2005.02.053 (Pubitemid 40718709)
    • (2005) Tetrahedron , vol.61 , Issue.16 , pp. 4031-4034
    • Esmaeili, A.A.1    Zendegani, H.2
  • 35
    • 67650047691 scopus 로고    scopus 로고
    • Reaction of isocyanides, dialkyl acetylenedicarboxylates, and α-Keto Lactones: Unexpected Participation of an Ester Carbonyl Group in the Isocyanide-based three-component reaction
    • doi:10.1055/s-0028-1088042
    • Esmaeili AA, Vesalipoor H (2009) reaction of isocyanides, dialkyl acetylenedicarboxylates, and α-Keto Lactones: Unexpected Participation of an Ester Carbonyl Group in the Isocyanide-based three-component reaction. Synthesis 1635-1638. doi:10.1055/s-0028-1088042
    • (2009) Synthesis , pp. 1635-1638
    • Esmaeili, A.A.1    Vesalipoor, H.2
  • 36
    • 77953239701 scopus 로고    scopus 로고
    • An efficient synthesis of highly functionalized 4H-Pyrano[3,2-d] isoxazoles via isocyanide-based three-component reaction
    • doi:10.1055/s-0029-1220072
    • Esmaeili AA, Hosseinabadi R, Habibi A (2010) An efficient synthesis of highly functionalized 4H-Pyrano[3,2-d]isoxazoles via isocyanide-based three-component reaction. Synlett 1477-1480. doi:10.1055/s-0029-1220072
    • (2010) Synlett , pp. 1477-1480
    • Esmaeili, A.A.1    Hosseinabadi, R.2    Habibi, A.3


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