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Synlett 2012; 23(13): 1973-1977
DOI: 10.1055/s-0032-1316587
DOI: 10.1055/s-0032-1316587
letter
Niobium Pentachloride Catalyzed Multicomponent Povarov Reaction
Further Information
Publication History
Received: 26 March 2012
Accepted after revision: 08 June 2012
Publication Date:
26 July 2012 (online)
Abstract
A single-step method for the synthesis of furan- and pyranoquinoline derivatives through multicomponent Povarov reactions between aniline derivatives, benzaldehyde and two different enol ethers (2,3-dihydrofuran and 3,4-dihydropyran) using niobium pentachloride as catalyst under mild conditions, providing good yields and high diastereoselectivity, is described.
Key words
niobium pentachloride - multicomponent Povarov reaction - furanoquinolines - pyranoquinolines - Lewis acidSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
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- 12 General Procedure for the Multicomponent Povarov Reaction of Benzaldehyde, Aniline Derivatives and Enol Ether with NbCl5 : To a solution of niobium pentachloride (10 mol% or 25 mol%) in anhyd MeCN (2.0 mL), maintained at r.t. under a nitrogen atmosphere, was added a solution of the benzaldehyde (1.0 mmol), 2,3-dihydrofuran or 3,4-dihydropyran (1.0 mmol) and the respective aniline (3a–g; 1.0 mmol) in anhyd MeCN (3.0 mL). After completion of the addition, stirring was continued at r.t. The reaction mixture was quenched with H2O addition (3.0 mL). The mixture was extracted with EtOAc (10.0 mL). The organic layer was separated and washed with sat. NaHCO3 solution (3 × 10.0 mL), sat. brine (2 × 10.0 mL), and then dried over anhyd MgSO4. The solvent was removed under vacuum and the products were purified by column chromatography through silica gel using mainly a mixture of hexane and EtOAc (9.0:1.0) as eluent. (3aS,4S,9bS)-4-Phenyl-2,3,3a,4,5,9b-hexahydrofuran-[3,2-c]quinoline (7a): 1H NMR (300 MHz, CDCl3): δ = 7.47 (d, 1 H, J 1 = 7.6 Hz), 7.40–7.43 (m, 5 H), 7.10 (dd, 1 H, J 1 = 8.0 Hz, J 2 = 7.0 Hz), 6.82 (dd, 1 H, J 1 = 7.6 Hz, J 2 = 7.0 Hz), 6.61 (d, 1 H, J = 8.0 Hz), 5.29 (d, 1 H, J = 7.9 Hz), 4.71 (d, 1 H, J = 2.4 Hz), 3.70–3.88 (m, 2 H), 2.80 (m, 1 H), 2.21 (m, 1 H), 1.55 (m, 1 H). 13C NMR (75 MHz, CDCl3): δ = 143.9 (C), 141.2 (C), 129.1 (CH), 127.6 (2 × CH), 127.3 (CH), 126.6 (CH), 125.5 (2 × CH), 121.7 (C), 118.2 (CH), 113.9 (CH), 74.9 (CH), 65.8 (CH2), 56.5 (CH), 44.8 (CH), 23.7 (CH2). IR (film): 3348, 2975, 2855, 1615, 1480, 1039 cm–1. MS: m/z = 251 [M]+, 220, 206, 174, 130, 115, 91, 77. (3aS,4R,9bS)-4-Phenyl-2,3,3a,4,5,9b-hexahydrofuran-[3,2-c]quinoline (8a): 1H NMR (300 MHz, CDCl3): δ = 7.37 (d, 1 H, J = 7.0 Hz), 7.27–7.35 (m, 5 H), 7.06 (dd, 1 H, J 1 = 8.3 Hz, J 2 = 7.0 Hz), 6.73 (dd, 1 H, J 1 = 8.3 Hz, J 2 = 7.7 Hz), 6.56 (d, 1 H, J = 7.7 Hz), 4.54 (d, 1 H, J = 4.9 Hz), 3.96 (m, 1 H), 3.77 (m, 1 H), 3.74 (d, 1 H, J = 11.2 Hz), 2.40 (m, 1 H), 1.95 (m, 1 H), 1.65 (m, 1 H). 13C NMR (75 MHz, CDCl3): δ = 145.8 (C), 142.1 (C), 131.6 (CH), 129.6 (CH), 129.1 (CH), 128.7 (CH), 128.6 (CH), 120.5 (CH), 118.8 (C), 115.1 (CH), 76.63 (CH), 65.6 (CH2), 58.2 (CH), 43.8 (CH), 29.3 (CH2). IR (film): 3348, 2975, 2855, 1615, 1480, 1039 cm–1. MS: m/z = 251 [M]+, 220, 206, 174, 130, 115, 91, 77. (4aS,5S,10bS)-5-Phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyran[3,2-c]quinoline (9a): 1H NMR (300 MHz, CDCl3): δ = 7.35–7.44 (m, 5 H), 7.30 (m, 1 H), 7.09 (dt, 1 H, J 1 = 7.7 Hz, J 2 = 0.8 Hz), 6.79 (dt, 1 H, J 1 = 7.7 Hz, J 2 = 1.0 Hz), 6.60 (dd, 1 H, J 1 = 7.7 Hz, J 2 = 0.8 Hz), 5.33 (d, 1 H, J = 5.6 Hz), 4.69 (d, 1 H, J = 2.3 Hz), 3.85 (NH, 1 H), 3.58 (m, 1 H), 3.43 (dt, 1 H, J 1 = 11.6 Hz, J 2 = 2.5 Hz), 2.16 (m, 1 H), 1.47–1.58 (m, 2 H), 1.43 (m, 1 H), 1.31 (m, 1 H). 13C NMR (75 MHz, CDCl3): δ = 145.6 (C), 141.5 (C), 129.2 (CH), 128.8 (CH), 128.7 (CH), 128.5 (CH), 128.0 (CH), 127.9 (CH), 127.2 (CH), 120.3 (C), 118.7 (CH), 114.8 (CH), 73.2 (CH), 61.0 (CH2), 59.7 (CH), 39.3 (CH), 25.8 (CH2), 18.4 (CH2). IR (film): 3312, 2941, 2865, 1608, 1486, 1317, 1265, 1069, 737 cm–1. MS: m/z = 265 [M]+, 234, 220, 194, 129, 117, 91, 77. (4aS,5R,10bS)-5-Phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyran[3,2-c]quinoline (10a): 1H NMR (300 MHz, CDCl3): δ = 7.30–7.44 (m, 5 H), 7.22 (dd, 1 H, J 1 = 7.7 Hz, J 2 = 1.3 Hz), 7.09 (dt, 1 H, J 1 = 7.7 Hz, J 2 = 1.3 Hz), 6.71 (dt, 1 H, J 1 = 7.3 Hz, J 2 = 0.7 Hz), 6.53 (dd, 1 H, J 1 = 7.7 Hz, J 2 = 0.7 Hz), 4.72 (d, 1 H, J = 10.9 Hz), 4.39 (d, 1 H, J = 2.8 Hz), 4.10 (dt, 1 H, J 1 = 11.4 Hz, J 2 = 2.3 Hz), 3.72 (dt, 1 H, J 1 = 11.4 Hz, J 2 = 2.5 Hz), 2.11 (m, 1 H), 1.84 (tdt, 1 H, J 1 = 13.4 Hz, J 2 = 12.4 Hz, J 3 = 4.5 Hz), 1.65 (tt, 1 H, J 1 = 13.4 Hz, J 2 = 4.5 Hz), 1.47 (m, 1 H), 1.33 (m, 1 H). 13C NMR (75 MHz, CDCl3): δ = 145.1 (C), 142.7 (C), 131.3 (CH), 129.8 (CH), 129.0 (2 × CH), 128.3 (2 × CH), 128.2 (CH), 121.0 (C), 117.9 (CH), 114.5 (CH), 74.9 (CH), 69.0 (CH2), 55.2 (CH), 39.3 (CH), 24.5 (CH2), 22.4 (CH2). IR (film): 3360, 2940, 2865, 1610, 1488, 1315, 1265, 1070, 737 cm–1. MS: m/z = 265 [M]+, 234, 220, 194, 129, 117, 91, 77