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Synlett
Volumn , Issue 17, 2007, Pages 2639-2642
A novel and facile method for the synthesis of 2,3-disubstituted quinolines by a three-component coupling reaction
Author keywords

Lewis acid; Quinolines; Regioselectively; Three component coupling reaction
Indexed keywords

4 METHYLANILINE; ALDEHYDE; AROMATIC AMINE; BENZALDEHYDE; LEWIS ACID; QUINOLINE;
EID: 35648965750     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991058     Document Type: Article
Times cited : (25)
References (38)
  • 2
    • 84944031181 scopus 로고    scopus 로고
    • Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Pergamon Press: Oxford/New York
    • (a) Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II, Vol. 5; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford/New York, 1996, 245.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 245
    • Balasubramanian, M.1    Keay, J.G.2
  • 10
    • 27744450163 scopus 로고    scopus 로고
    • For recent reports on the synthesis of quinoline derivatives, see: a
    • For recent reports on the synthesis of quinoline derivatives, see: (a) Duvelleroy, D.; Perrio, C.; Parisel, O.; Lasne, M.-C. Org. Biomol. Chem. 2005, 3, 3794.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 3794
    • Duvelleroy, D.1    Perrio, C.2    Parisel, O.3    Lasne, M.-C.4
  • 27
    • 0141855373 scopus 로고    scopus 로고
    • There are a few reports for the synthesis of 2-aryl-3-carboalkoxy quinoline using Friedländer reaction. For examples, see: (a) Patteux, C.; Levacher, V.; Dupas, G. Org. Lett. 2003, 5, 3061.
    • There are a few reports for the synthesis of 2-aryl-3-carboalkoxy quinoline using Friedländer reaction. For examples, see: (a) Patteux, C.; Levacher, V.; Dupas, G. Org. Lett. 2003, 5, 3061.
  • 29
    • 35649025434 scopus 로고    scopus 로고
    • When this reaction was carried out at reflux in toluene, the major product was the 1,4-dihydropyridines. The investigation regarding the synthesis of 1,4-dihydropyridines will be reported elsewhere in due course.
    • When this reaction was carried out at reflux in toluene, the major product was the 1,4-dihydropyridines. The investigation regarding the synthesis of 1,4-dihydropyridines will be reported elsewhere in due course.
  • 30
    • 35649013303 scopus 로고    scopus 로고
    • We performed this reaction using TfOH (10 mol%) at reflux in EtOH, and obtained the quinoline 4aa in 50% yield..
    • We performed this reaction using TfOH (10 mol%) at reflux in EtOH, and obtained the quinoline 4aa in 50% yield..
  • 31
    • 35649000102 scopus 로고    scopus 로고
    • General Procedure: To the EtOH (5 mL) solution of 1a (53.9 mg, 0.5 mmol, 2a (55 μL, 0.54 mmol) and Lewis acid (0.05 mmol, 10 mol, was added 3 (61 μL, 0.6 mmol) using a microsyringe and then the mixture was refluxed for 24 h. The reaction was quenched with sat. aq NaHCO 3 and the mixture was extracted with EtOAc. The combined organic layers were dried over MgSO4. The organic layer was filtered and concentrated under reduced pressure. The yield of 4aa was determined by GC using biphenyl as the internal standard. The quinoline 4aa was purified by preparative TLC (SiO2; hexane-EtOAc, 7:1) and/or recycling preparative HPLC (GPC column, CHCl3 as an eluent) and was fully characterized. Ethyl 6-Methyl-2-phenylquinoline-3-carboxylate (4aa, 1H NMR (300 MHz, CDCl3, δ, 1.06 (t, J, 6.9 Hz, 3 H, 2.55 (s, 3 H, 4.17 (q, J, 6.9 Hz, 2 H, 7.44 m, 3 H, 7
    • 3): δ = 13.6, 21.5, 61.4, 125.4, 125.8, 126.8, 128.1, 128.3, 128.4, 129.1, 133.8, 137.2, 138.3, 140.8, 146.9, 157.2, 168.1.
  • 32
    • 35649016741 scopus 로고    scopus 로고
    • 3 yielded the quinoline 4aa in 60% yield.
    • 3 yielded the quinoline 4aa in 60% yield.
  • 33
    • 35648961972 scopus 로고    scopus 로고
    • CCDC 650434 contains the supplementary crystallographic data for compound 4ha. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
    • CCDC 650434 contains the supplementary crystallographic data for compound 4ha. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
  • 34
    • 35648997526 scopus 로고    scopus 로고
    • Typical Procedure (Scheme 2, To the EtOH (7 mL) solution of 1a (107.2 mg, 1.0 mmol, 2d (110 μL, 1.1 mmol, which was distilled from P2O5 before use, and Sc(OTf)3 (49.2 mg, 0.10 mmol) was added 3 (122 μL, 1.2 mmol) using a microsyringe and then the mixture was refluxed for 24 h. The reaction was quenched with sat. aq NaHCO3 and the mixture was extracted with EtOAc. The combined organic layers were dried over MgSO4. This organic layer was filtered and concentrated under reduced pressure. The residue was purified by short column chromatography (hexane-EtOAc, 6:1) and recycling preparative HPLC (GPC column, CHCl3 as an eluent) to give the pure 4ad in 34% yield. Diethyl 6-Methylquinoline-2,3-dicarboxylate (4ad, 1H NMR (300 MHz, CDCl3, δ, 1.45 (m, 6 H, 2.57 (s, 3 H, 4.43 (q, J, 7.0 Hz, 2 H, 4.52 (q, J, 7.0 Hz, 2 H, 7.67 m, 2 H
    • 3): δ = 14.1, 21.6, 61.4, 62.2, 122.5, 127.1, 127.3, 129.4, 134.6, 138.7, 138.9, 146.6, 147.0, 165.3, 166.9.
  • 35
    • 1542509637 scopus 로고    scopus 로고
    • The CuOTf-catalyzed 1,4-addition of EtOH to ethyl propiolate has been reported. See: Bertz, S. H.; Dabbagh, G.; Cotte, P. J. Org. Chem. 1982, 47, 2216.
    • The CuOTf-catalyzed 1,4-addition of EtOH to ethyl propiolate has been reported. See: Bertz, S. H.; Dabbagh, G.; Cotte, P. J. Org. Chem. 1982, 47, 2216.
  • 38
    • 35648992044 scopus 로고    scopus 로고
    • In this reaction, ethyl 3,3-diethoxypropionate was obtained predominantly
    • In this reaction, ethyl 3,3-diethoxypropionate was obtained predominantly.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.