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Organocatalytic Oxidative Enamine Catalysis and 1,5-Hydride Transfer/Cyclization: Synthesis of Tetrahydroquinoline Derivatives

  • Kim, Mi Hyun (Department of Chemistry, Soonchunhyang University) ;
  • Kim, Dae Young (Department of Chemistry, Soonchunhyang University)
  • Received : 2013.08.05
  • Accepted : 2013.09.20
  • Published : 2013.12.20
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Abstract

Keywords

Experimental

General Procedure for the Synthesis of Tetrahydroquinoline Derivatives 2: To a stirred solution of 3-(o-(dialkylamino) aryl)propanals 1 (0.3 mmol) in CH2Cl2 (1.0 mL) was added DDQ (68.1 mg, 0.3 mmol), racemic diarylprolinol silylether catalyst III (35.9 mg, 0.06 mmol), and DNBS (14.9 mg, 0.06 mmol). The mixture was refluxed for 0.5-7 d, diluted with saturated NaHCO3 solution (10 mL) and extracted with ethyl acetate (2 × 15 mL). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified by flash chromatography (EtOAc/hexane = 1:10) to afford tetrahydroquinoline derivatives 2.

6R,6aS)-5,6,6a,7,8,9,10,11,12,13-Decahydroazonino[1,2- a]quinoline-6-carbaldehyde (2a): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.83 (d, J = 0.8 Hz, 1H), 7.14- 7.07 (m, 2H), 6.80-6.77 (m, 1H), 6.70 (td, J = 7.2 Hz, 1.2 Hz, 1H), 3.76 (dt, J = 10.8 Hz, 2.4 Hz, 1H), 3.67 (ddd, J = 14.8 Hz, 8.0 Hz, 3.6 Hz, 1H), 3.22 (ddd, J = 14.8 Hz, 6.8 Hz, 3.6 Hz, 1H), 3.05-2.98 (m, 1H), 2.87 (dd, J = 16.8 Hz, 5.6 Hz, 1H), 2.70-2.65 (m, 1H), 1.84-1.10 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 203.21, 144.97, 129.77, 127.35, 120.33, 117.04, 115.24, 58.88, 56.79, 48.00, 28.87, 27.62, 27.25, 25.44, 25.09, 24.74, 23.33; EI-MS: m/z 258.1 [M+H]+; ESIHRMS: m/z calcd for C17H24NO [M+H]+: 258.1861; found 258.1858.

(6R,6aR)-6,6a,7,8,9,10,11,12-Octahydro-5H-azocino[1,2- a]quinoline-6-carbaldehyde (2b): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.50 (d, J = 0.4 Hz, 1H), 7.08- 7.03 (m, 2H, 6.61-6.54 (m, 2H), 3.84-3.79 (m, 2H), 3.24- 3.21 (m, 1H), 3.20-3.06 (m, 2H), 2.54-2.51 (m, 1H), 2.01- 1.32 (m, 10H); 13C NMR (100 MHz, CDCl3) δ 203.32, 143.98, 129.52, 127.54, 117.37, 115.53, 111.33, 55.45, 53.15, 48.65, 33.90, 27.82, 26.91, 26.26, 26.09, 24.17; EI-MS: m/z 244.1 [M+H]+; ESI-HRMS: m/z calcd for C16H22NO [M+H]+: 244.1701; found 244.1697.

(6R,6aS)-5,6,6a,7,8,9,10,11-Octahydroazepino[1,2-a]quinoline- 6-carbaldehyde (2c): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.55 (s, 1H), 7.06-7.01 (m, 2H), 6.52- 6.54 (m, 1H), 6.40-6.48 (m, 1H), 3.85 (dd, J = 6.0 Hz, 3.0 Hz, 1H), 3.82-3.79 (m, 1H), 3.22-3.09 (m, 2H), 3.02 (dd, J = 8.0 Hz, 6.5 Hz, 1 H), 2.54-2.52 (m, 1H), 1.81-1.95 (m, 1H), 1.67-1.57 (m, 6H), 1.37-1.34 (m, 1H) ; 13C NMR (100 MHz, CDCl3) δ 203.17, 144.90, 129.50, 127.53, 117.15, 115.67, 110.39, 58.26, 49.58, 47.95, 35.02, 26.63, 26.13, 25.94, 23.80; EI-MS: m/z 230.1 [M+H]+; ESI-HRMS: m/z calcd for C15H20NO [M+H]+: 230.1545; found 230.1541.

(4aS,5R)-2,3,4,4a,5,6-Hexahydro-1H-pyrido[1,2-a]quinoline- 5-carbaldehyde (2d): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.63 (d, J = 1.6 Hz, 1H), 7.10 (td, J = 8.4 Hz, 1.6 Hz, 1H), 7.03-7.01 (m, 1H), 6.78-6.76 (m, 1H), 6.67 (td, J = 7.2 Hz, 0.8 Hz, 1H), 3.95-3.91 (m, 1H), 3.45 (ddd, J = 10.8 Hz, 5.2 Hz, 2.0 Hz, 1H), 2.99 (dd, J = 15.2 Hz, 6.4 Hz, 1H), 2.90-2.84 (m, 2H), 2.63-2.58 (m, 1H), 1.90- 1.50 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 202.72, 145.73, 128.89, 127.65, 122.10, 117.62, 112.60, 56.53, 52.01, 48.39, 31.26, 25.99, 24.98, 24.06; EI-MS: m/z 216.1 [M+H]+.

(3aS,4R)-1,2,3,3a,4,5-Hexahydropyrrolo[1,2-a]quinoline- 4-carbaldehyde (2e): Major diastereoisomer; 1H NMR (400 MHz, CDCl3) δ 9.91 (d, J = 2.0 Hz, 1H), 7.11-7.08 (m, 1H), 7.35 (d, J = 7.0 Hz, 1H), 6.60-6.57 (m, 1H), 6.44 (d, J = 8.0 Hz, 1H) 3.49 (ddd, J = 10.4 Hz, 10.1 Hz, 4.9 Hz, 1H), 3.38 (ddd, J = 11.1 Hz, 8.9 Hz, 2.1 Hz, 1H), 3.22-3.17 (m, 1H), 2.93-2.91 (m, 2H), 2.50-2.41 (m, 1H), 2.32-2.28 (m, 1H), 2.13-2.10 (m, 1H), 1.97-1.95 (m, 1H), 1.58-1.54 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 202.99, 143.89, 128.70, 127.76, 119.06, 115.48, 110.45, 57.75, 50.35, 46.64, 31.62, 28.59, 24.02; EI-MS: m/z 202.1 [M+H]+; ESI-HRMS: m/z calcd for C13H16NO [M+H]+: 202.1232; found 202.1238.

(6R,6aS)-3-Bromo-5,6,6a,7,8,9,10,11,12,13-decahydroazonino[ 1,2-a]quinoline-6-carbaldehyde (2f): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.81 (d, J = 0.8 Hz, 1H), 7.19-7.17 (m, 2H), 6.65-6.62 (m, 1H), 3.76 (dt, J = 10.4 Hz, 2.8 Hz, 1H), 3.61 (ddd, J = 14.8 Hz, 7.6 Hz, 3.2 Hz, 1H), 3.21 (ddd, J = 14.8 Hz, 6.8 Hz, 3.2 Hz, 1H), 3.01 (dd, J = 16.8 Hz, 13.6 Hz, 1H), 2.82 (dd, J = 17.2 Hz, 5.6 Hz, 1H), 2.67-2.61 (m, 1H), 1.90-1.10 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 202.46, 143.95, 132.07, 130.11, 122.40, 116.58, 108.80, 58.92, 56.75, 47.82, 28.81, 27.46, 27.10, 25.51, 25.16, 24.74, 23.15; EI-MS: m/z 336.0 [M+H]+.

(6R,6aS)-3-Fluoro-5,6,6a,7,8,9,10,11,12,13-decahydroazonino[ 1,2-a]quinoline-6-carbaldehyde (2g): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.82 (d, J = 0.4 Hz, 1H), 6.86-6.77 (m, 2H), 6.71 (dd, J = 8.8 Hz, 4.8 Hz, 1H), 3.75 (dt, J = 11.2 Hz, 2.8 Hz, 1H), 3.54 (ddd, J = 14.8 Hz, 8.4 Hz, 3.6 Hz, 1H), 3.21 (ddd, J = 14.8 Hz, 6.4 Hz, 3.2 Hz, 1H), 3.03 (dd, J = 16.4 Hz, 13.6 Hz, 1H), 2.82 (dd, J = 16.8 Hz, 5.2 Hz, 1H), 2.70-2.64 (m, 1H), 1.90-1.25 (m, 11H), 1.15-1.05 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 202.77, 155.38 (d, J = 234.7 Hz), 141.38, 121.78 (d, J = 7.1 Hz), 116.55 (d, J = 8.4 Hz), 115.62 (d, J = 21.7 Hz), 114.08 (d, J = 22.0 Hz), 58.20, 57.21, 47.47, 28.52, 27.53, 27.44, 24.89, 24.55, 24.31, 23.38; EI-MS: m/z 276.1 [M+H]+.

(6R,6aS)-3-(Trifluoromethyl)-5,6,6a,7,8,9,10,11,12,13- decahydroazonino[1,2-a]quinoline-6-carbaldehyde (2h): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.50 (s, 1H), 7.30-7.28 (m, 2H), 6.66-6.64 (m, 1H), 3.92-3.88 (m, 1H), 3.72 (ddd, J = 12.4 Hz, 6.4 Hz, 3.2 Hz, 1H), 3.27 (ddd, J = 15.2 Hz, 7.6 Hz, 3.2 Hz, 1H), 3.18-3.14 (m, 1H), 3.12- 3.10 (m, 1H), 2.61 (dt, J = 6.4 Hz, 2.4 Hz, 1H), 1.90-1.30 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 202.31, 147.19, 126.57 (q, J = 3.6 Hz), 124.60 (q, J = 4.1 Hz), 123.81 (q, J = 265.2), 117.19, 116.99 (q, J = 32.2 Hz), 110.71, 59.84, 56.65, 48.75, 33.22, 30.92, 27.69, 26.57, 26.39, 25.35, 23.75; EI-MS: m/z 326.1 [M+H]+.

(6R,6aS)-2-Chloro-5,6,6a,7,8,9,10,11,12,13-decahydroazonino[ 1,2-a]quinoline-6-carbaldehyde (2i): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.81 (d, J = 0.4 Hz, 1H), 6.98-6.96 (m, 1H), 6.72-6.70 (m, 1H), 6.64 (dd, J = 8.0 Hz, 2.0 Hz, 1H), 3.77 (dt, J = 10.8 Hz, 2.4 Hz, 1H), 3.64 (ddd, J = 15.2 Hz, 7.2 Hz, 3.6 Hz, 1H), 3.22 (ddd, J = 14.8 Hz, 7.2 Hz, 3.6 Hz, 1H), 3.02-2.94 (m, 1H), 2.82 (dd, J = 17.2 Hz, 5.6 Hz, 1H), 2.64 (ddd, J = 13.6 Hz, 5.2 Hz, 4 Hz, 1H), 1.90-1.10 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 202.53, 145.92, 132.75, 130.66, 118.62, 116.85, 114.40, 58.98, 56.75, 48.11, 29.06, 27.40, 17.10, 25.60, 25.24, 24.77, 22.87; EI-MS: m/z 292.1 [M+H]+.

(6R,6aS)-2-Methoxy-5,6,6a,7,8,9,10,11,12,13-decahydroazonino[ 1,2-a]quinoline-6-carbaldehyde (2j): Major diastereomer; 1H NMR (400 MHz, CDCl3) δ 9.81 (d, J = 0.8 Hz, 1H), 7.00-6.98 (m, 1H), 6.31-6.29 (m, 2H), 3.78 (s, 3H), 3.73-3.64 (m, 2H), 3.22 (ddd, J = 15.2 Hz, 7.2 Hz, 3.6 Hz, 1H), 3.00-2.94 (m, 2H), 2.82 (dd, J = 16.0 Hz, 5.2 Hz, 2.68- 2.63 (m, 1H), 1.90-1.10 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 203.26, 159.20, 145.91, 130.24, 113.04, 102.10, 100.95, 59.19, 56.80, 55.19, 48.52, 29.02 27.63, 27.16, 25.62, 25.30, 24.86, 22.69; EI-MS: m/z 288.1 [M+H]+.

(12bR,13R)-6,7,8,12b,13,14-Hexahydrobenzo[3,4]azepino[ 1,2-a]quinoline-13-carbaldehyde (2k): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 9.64 (d, J = 1.6 HZ, 1H), 7.18-7.02 (m, 6H), 6.67-6.58 (m, 2H), 5.05 (d, J = 6.4 Hz, 1H), 2.99-2.90 (m, 2H), 2.65 (dt, J = 14 Hz, 4.8 Hz, 1H), 2.27-2.19 (m, 1H), 1.68-1.61 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 203.02, 143.42, 139.63, 139.28, 130.80, 129.28, 127.86, 127.65, 127.16, 126.54, 119.34, 116.07, 110.66, 63.26, 49.49, 46.33, 31.88, 26.72, 24.73; EI-MS: m/z 278.1 [M+H]+.

(11bR,12R)-7,11b,12,13-Tetrahydro-6H-isoquinolino[2,1- a]quinoline-12-carbaldehyde (2l): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 9.39 (s, 1H), 7.33-7.28 (m, 2H), 7.24-7.19 (m, 2H), 7.14-7.10 (m, 2H), 6.85-6.83 (m, 1H), 6.79 (td, J = 7.2 Hz, 0.8 Hz, 1H), 4.66-4.67 (m, 1H), 4.01- 3.97 (m, 1H), 3.41 (d, J = 16.8 Hz, 1H), 3.29 (dt, J = 7.2 Hz, 1.6 Hz, 1H), 3.17 (dd, J = 16.4 Hz, 6.8 Hz, 1H), 3.08-3.04 (m, 1H), 3.02-2.99 (m, 1H), 2.93-2.89 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 202.02, 146.38, 135.36, 134.98, 129.86, 128.81, 126.95, 126.83, 126.24, 121.32, 118.87, 112.11 (one aromatic carbon missing), 57.61, 51.21, 42.06, 29.89, 27.67; EI-MS: m/z 264.1 [M+H]+.

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