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Step 1 General/Typical Procedure: General procedure A. Synthesis of compounds 4, 5, 6 and 7. Molecular sieves 4Å (ca. 2g) and a Sc(OTf)3 (0.2 mmol) were added to a solution of aldehyde (1 mmol) and aniline (1 mmol) in dry CH3CN (4 mL), and the mixture was stirred at room temperature. After 5 min, a solution of the unsaturated lactam (1 mmol) in dry CH3CN (3 mL) was added, and the resulting suspension was stirred under argon atmosphere at the same temperature for 48 h. An aqueous saturated NaHCO3 solution (10 mL) was added, and the resulting mixture was extracted with EtOAc (3×10 mL). The organic phase was dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography (hexane- EtOAc) to give the desired products. (4aRS, 5RS, 10bRS)-ethyl 1-benzyl-5-(furan-2-yl)-2-oxo-1,2,3,4,4a,5,6,10boctahydrobenzo[ h][1,6]naphthyridine-9-carboxylate (4b) Following the general procedure A, the reaction between 1a, ethyl 4-aminobenzoate and 2-furaldehyde, and after a flash chromatography afforded compound 4b as a pink powder (38%). 1H-NMR (400 MHz, CDCl3) d: 7.72 (dd, J= 1.9, 8.4 Hz, 1H), 7.67-7.64 (m, 1H), 7.20-7.12 (m, 4H), 7.08-7.02 (m, 2H), 6.44 (d, J= 8.4 Hz, 1H), 6.14 (dd, J= 1.8,3.2 Hz, 1H), 5.89-5.85 (m, 1H), 5.50 (d, J= 14.7 Hz, 1H), 4.70 (br s, 1H), 4.35 (d, J= 4.0, 1H), 4.31 (d, J= 4.5 Hz, 1H), 4.29-4.21 (m, 2H), 4.01 (d, J= 14.8 Hz, 1H), 2.53-2.30 (m, 3H), 1.90-1.78 (m, 1H), 1.70-1.57 (m, 1H), 1.29 (t, J= 7.12 Hz, 3H) ppm. 13C-NMR (100 MHz, CDCl3) d: 170.7, 166.4, 154.7, 146.2, 142.4, 137.2, 130.8, 129.6, 128.4, 128.0, 127.3, 119.2, 117.7, 112.9, 110.1, 106.6, 60.4, 53.5, 51.8, 49.8, 34.8, 29.8, 21.9, 14.5 ppm. IR (film) nmax: 3321, 2975, 2930, 1700, 1630, 1609, 1521, 1367, 1284, 1252, 1188, 1108, 1009, 765 cm-1 . HRMS: calcd for C26H27N2O4, 431.1965 (M+H+); found, 431.1956. Step 2 General procedure B. Synthesis of compounds 8, 9 and 10. To a solution of compound 4 (1 mmol) in 15 mL of CHCl3, DDQ (2 mmol) was added, and the mixture was stirred 24 h in an open vessel at room temperature. An aqueous saturated NaHCO3 solution (10 mL) was added, and the resulting mixture was extracted with CHCl3 (3×10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The reaction mixture was purified with flash chromatography (hexane- EtOAc) to afford the desired product. ethyl 1-benzyl-5-(furan-2-yl)-2-oxo-1,2,3,4- tetrahydrobenzo[h][1,6]naphthyridine- 9-carboxylate (8a) Following the general procedure B, the oxidation of 4b, afforded compound 8a as brownish solid (69%). 1H-NMR (400 MHz, CDCl3) d : 8.68 (d, J= 1.7 Hz, 1H), 8.25 (dd, J= 1.7, 8.8 Hz, 1H), 8.19-8.11 (m, 1H), 7.67-7.65 (m, 1H), 7.25- 7.16 (m, 4H), 7.12-7.07 (m, 2H), 6.63 (dd, J= 1.8, 3.4 Hz, 1H), 5.37 (s, 2H), 4.35 (q, J= 7.1 Hz, 2H), 3.34-3.29 (m, 2H), 2.74- 2.69 (m, 2H), 1.35 (t, J= 7.1 Hz, 3H) ppm. 13C-NMR (100 MHz, CDCl3) d : 172.6, 166.1, 144.6, 137.2, 130.4, 129.2, 129.2, 128.8, 128.2, 128.0, 127.8, 127.7, 127.4, 126.2, 121.5, 119.3, 114.1, 114.1, 112.3, 61.6, 52.8, 32.5, 22.7, 14.6 ppm. IR (film) nmax: 3353, 3110, 2969, 1700, 1566, 1431, 1380, 1265, 1143, 746 cm-1 . HRMS: calcd for C26H23N2O4, 427.1652 (M+H+); found, 427.1644. |
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2015-05-16 21:03:52, 26.49 K
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