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Organocatalytic Synthesis of Tetrahydroquinolines from α,β-Unsaturated Ketones via 1,5-Hydride Transfer/Cyclization

  • Received : 2013.07.28
  • Accepted : 2013.08.05
  • Published : 2013.11.20
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Abstract

Keywords

Experimental Section

General. All commercial reagents and solvents were used without purification. TLC analyses were carried out on precoated silica gel plates with F254 indicator. Visualization was accomplished by UV light (254 nm), I2, p-anisaldehyde, ninhydrin, and phosphomolybdic acid solution as an indicator. Purification of reaction products was carried out by flash chromatography using E. Merck silica gel 60 (230-400 mesh). 1H NMR and 13C NMR spectra were recorded on a Bruker DRX 400 (400 MHz for 1H, 100 MHz for 13C) and AC 200 (200 MHz for 1H, 50 MHz for 13C). Chemical shift values (δ) are reported in ppm relative to Me4Si (0.0 ppm).

General Procedure for the Catalytic Enantioselective 1,5-Hydride Transfer/Cyclization of β-(o-(Dialkylamino)-aryl)-α,β-unsaturated Ketones 1: To a stirred solution of β-(o-(dialkylamino)aryl)-α,β-unsaturated ketone 1 (0.3 mmol) and HOTf (16 μL, 0.18 mmol) in THF (0.3 mL) was added benzyl amine (9.8 μL, 0.09 mmol). The mixture was refluxed for 10-48 h, diluted with saturated NaHCO3 solution (10 mL) and extracted with ethyl acetate (2 × 10 mL). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified by flash chromatography to afford tetrahydroquinoline derivatives 2.

1-(1,2,3,3a,4,5-Hexahydropyrrolo[1,2-a]quinolin-4-yl)-ethanone (2a): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.11 (td, J = 8.0 Hz, 1.6 Hz, 1H), 7.03-7.02 (m, 1H), 6.58 (td, J = 7.2 Hz, 0.8 Hz, 1H), 6.45-6.43 (m, 1H), 3.49 (ddd, J = 15.2 Hz, 10.8 Hz, 5.2 Hz, 1H), 3.40 (ddd, J = 10.8 Hz, 9.2 Hz, 1.6 Hz, 1H), 3.19 (ddd, J = 18.8 Hz, 9.6 Hz, 7.6 Hz, 1H), 2.90-2.87 (m, 2H), 2.49 (ddd, J = 16.4 Hz, 9.6 Hz, 6.4 Hz, 1H), 2.29 (s, 3H), 2.25-1.87 (m, 3H), 1.50-1.37 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 208.21, 143.52, 128.45, 127.70, 119.83, 115.04, 110.14, 59.23, 50.37, 46.88, 31.96, 31.75, 30.53, 23.99.

1-(2,3,4,4a,5,6-Hexahydro-1H-pyrido[1,2-a]quinolin-5-yl)ethanone (2b): Major diastereomer. 1H NMR (200 MHz, CDCl3) δ 7.10-7.00 (m, 2H), 6.61-6.40 (m, 2H), 3.45-3.38 (m, 2H), 3.19-3.10 (m, 1H), 2.90-2.80 (m, 2H), 2.50-2,45 (m, 1H), 2.29 (s, 3H), 2.25-1.30 (m, 6H); 13C NMR (50 MHz, CDCl3) δ 208.4, 143.3, 128.3, 127.5, 119.7, 115.1, 110.5, 59.3, 50.37, 49.8, 35.5, 31.9, 28.4, 26.5, 23.7.

1-(5,6,6a,7,8,9,10,11-Octahydroazepino[1,2-a]quinolin-6-yl)ethanone (2c): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.06-7.00 (m, 2H), 6.58-6.53 (m, 2H), 3.80-3.74 (m, 2H), 3.15 (ddd, J = 15.2 Hz, 10.4 Hz, 4.8 Hz, 1H), 3.07-2.96 (m, 2H), 2.66-2.62 (m, 1H), 2.13 (s, 3H), 2.10-1.95 (m,1 H), 1.80-1.37 (m, 7H); 13C NMR (100 MHz, CDCl3) δ 209.57, 144.01, 128.96, 127.47, 118.56, 115.32, 110.20, 58.92, 49.56, 49.23, 35.43, 28.17, 26.95, 26.69, 26.47, 25.59.

1-(3-Bromo-5,6,6a,7,8,9,10,11-octahydroazepino[1,2-a]-quinolin-6-yl)ethanone (2d): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.11-7.09 (m, 2H), 6.40-6.38 (m, 2H), 3.81-3.71 (m, 2H), 3.14 (ddd, J = 15.6 Hz, 11.6 Hz, 5.2 Hz, 1H), 3.04 (dd, J = 16.8 Hz, 3.6 Hz, 1H), 2.96 (dd, J = 16.8 Hz, 5.6 Hz, 1H), 2.65-2.62 (m, 1H), 2.13 (s, 3H), 2.07-1.95 (m, 1H), 1.80-1.30 (m, 7H); 13C NMR (100 MHz, CDCl3) δ 208.87, 142.85, 131.35, 130.02, 120.60, 111.79, 106.90, 58.96, 49.41, 49.14, 35.39, 37.92, 26.56, 26.39, 25.72, 25.65.

1-(6,6a,7,8,9,10,11,12-Octahydro-5H-azocino[1,2-a]quinolin-6-yl)ethanone (2e): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.08-7.04 (m, 1H), 7.01-6.99 (m, 1H), 6.59-6.53 (m, 2H), 3.79-3.70 (m, 2H), 3.24 (ddd, J = 14.8 Hz, 10.8 Hz, 3.6 Hz, 1H), 3.03 (d, J = 4.8 Hz, 2H), 2.66-2.63 (m, 1H), 2.10 (s, 3H), 2.00-1.40 (m, 10H); 13C NMR (100 MHz, CDCl3) δ 209.57, 144.12, 128.98, 127.47, 118.53, 115.26, 111.11, 59.29, 52.60, 49.57, 33.67, 28.07, 27.70, 27.28, 26.72, 26.21, 25.94.

1-(5,6,6a,7,8,9,10,11,12,13-Decahydroazonino[1,2-a]-quinolin-6-yl)ethanone (2f): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.13-7.09 (m, 1H), 7.07-7.05 (m, 1H), 6.77-6.75 (m, 1H), 6.68 (td, J = 7.2 Hz, 0.8 Hz, 1H), 3.71-3.65 (m, 2H), 3.23 (ddd, J = 15.2 Hz, 7.2 Hz, 4.0 Hz, 1H), 3.07 (dd, J = 18.0 Hz, 14.8 Hz, 1H), 2.77-2.69 (m, 2H), 2.26 (s, 3H), 1.92-1.41 (m, 10H), 1.35-0.80 (m, 2H), 13C NMR (100 MHz, CDCl3) δ 209.13, 144.65, 129.71, 127.16, 121.09, 116.87, 114.93, 60.44, 56.92, 48.58, 28.74, 28.04, 27.70, 27.30, 25.51, 25.11, 24.94, 24.70.

1-(3-Bromo-5,6,6a,7,8,9,10,11,12,13-decahydroazonino-[1,2-a]quinolin-6-yl)ethanone (2g): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.18-7.16 (m, 2H), 6.32-6.61 (m, 1H), 3.72-3.68 (m, 1H), 3.63 (ddd, J = 14.8 Hz, 7.6 Hz, 3.6 Hz, 1H), 3.23 (ddd, J = 15.2 Hz, 3.6 Hz, 7.2 Hz, 1H), 3.04 (dd, J = 18.0 Hz, 14.4 Hz, 1H), 2.73-2.66 (m, 2H), 2.26 (s, 3H), 1.92-1.40 (m, 10H), 1.30-1.20 (m, 1H), 1.17-0.80 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 208.49, 143.61, 131.99, 129.90, 123.19, 116.26, 108.62, 60.51, 56.89, 48.37, 28.75, 27.98, 27.53, 27.14, 25.57, 25.16, 24.92, 24.51.

1-(3-(Trifluoromethyl)-5,6,6a,7,8,9,10,11,12,13-decahydroazonino[1,2-a]quinolin-6-yl)ethanone (2h): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.33-7.26 (m, 2H), 6.75-6.73 (m, 1H), 3.80-3.74 (m, 2H), 3.28 (ddd, J = 15.2 Hz, 7.2 Hz, 4.0 Hz, 1H), 3.09 (dd, J = 16.8 Hz, 13.6 Hz, 1H), 2.79 (dd, J = 16.8 Hz, 4.8 Hz, 1H), 2.71 (ddd, J = 13.2 Hz, 4.8 Hz, 3.2 Hz, 1H), 2.27 (s, 3H), 1.95-1.15 (m, 12H) ); 13C NMR (100 MHz, CDCl3) δ 208.23, 141.93, 126.67 (q, J = 4.0 Hz), 125.03 (q, J = 267.0 Hz), 124.35 (q, J = 4.0 Hz), 120.50, 118.02 (q, J = 32.0 Hz), 113.38, 61.06, 56.52, 48.76, 28.74, 28.47, 27.47, 26.83, 26.04, 25.62, 25.33, 24.74.

1-(5,6,6a,7,8,9,10,11,12,13-Decahydroazonino[1,2-a]-quinolin-6-yl)propan-1-one (2i): 2.3:1 Diastereomeric mixture. 1H NMR (400 MHz, CDCl3) δ 7.05-7.01 (m, 1H), 7.00-6.92 (m, 2H), 6.70-6.68 (m, 1H), 6.62-6.50 (m, 2H), 3.72-3.51 (m, 3H), 2.69-2.63 (m, 2H), 2.58-2.57 (m, 0.5H), 2.50-2.35 (m, 3H), 1.85-0.5 (m, 18H), 1.03 (t, J = 7.2 Hz, 3H), 0.87 (t, J = 7.2 Hz, 1.5H); 13C NMR (100 MHz, CDCl3) δ 210.89, 210.61, 143.98, 143.64, 128.64, 127.90, 126.22, 126.07, 120.17, 118.33, 115.76, 114.90, 113.85, 112.09, 59.94, 59.53, 55.85, 55.58, 53.12, 53.05, 47.82, 46.59, 33.34, 32.27, 32.13, 27.33, 26.96, 26.67, 26.28, 25.93, 25.15, 25.12, 24.47, 24.07, 23.88, 23.68, 6.84, 6.69.

1-(5,6,6a,7,8,9,10,11,12,13-decahydroazonino[1,2-a]quinolin-6-yl)-3-phenylpropan-1-one (2j): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 7.31-7.18 (m, 5H), 7.11-7.07 (m, 1H), 7.06-7.03 (m, 1H), 6.75-6.73 (m, 1H), 6.67 (td, J = 7.2 Hz, 1.2 Hz, 1H), 3.67-3.58 (m, 2H), 3.21-3.14 (m, 1H), 3.13-3.06 (m, 1H), 3.05-3.00 (m, 1H), 2.99-2.93 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.75-2.65 (m, 2H), 1.90-1.19 (m, 11H), 1.03-0.97 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 210.11, 144.64, 141.10, 129.69, 128.59, 128.42, 127.13, 126.25, 121.11, 116.87, 114.96, 60.39, 56.89, 40.08, 43.02, 29.74, 27.93, 27.68, 27.29, 25.48, 25.10, 24.84, 24.58.

(5,6,6a,7,8,9,10,11,12,13-Decahydroazonino[1,2-a]quinolin-6-yl)(3-nitrophenyl)methanone (2k): Major diastereomer. 1H NMR (400 MHz, CDCl3) δ 8.71-8.70 (m, 1H), 8.43-8.41 (m, 1H), 8.20-8.17 (m, 1H), 7.70-7.16 (m, 1H), 7.12-7.07 (m, 1H), 6.98-6.97 (m, 1H), 6.70-6.68 (m, 1H), 6.62 (td, J = 7.2 Hz, 0.8 Hz, 1H), 3.77-3.73 (m, 1H), 3.71-3.67 (m, 1H), 3.66-3.59 (m, 1H), 3.14 (dd, J = 16.8 Hz, 6.4 Hz, 1H), 3.06-2.97 (m, 2H), 1.90-1.40 (m, 12H); 13C NMR (100 MHz, CDCl3) δ 198.53, 148.67, 144.79, 133.77, 130.09, 128.81, 127.32, 122.87, 119.46, 116.52, 113.46 (two aromatic carbons missing), 61.24, 56.57, 44.35, 32.89, 28.48, 27.18, 26.84, 25.90, 25.73, 24.93.

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