1 Hz94 (d, 1H, 3 J H 5' -H 6' = 8.4 Hz, H 5' ), 5.46 (d, 2H, 3 J H a -F = 49.2 Hz91 (s, 3H, H c ), 3.08 (m, 1H, H d ), 1.23 (m, 2H, H e or H e' ), 0.83 (m, 2H, H e or H e' ); 13 C NMR (CDCl 3 , 100 MHz) ? 155, pp.131-137 ,
34 (s, 3H, H a ), 1.25 (m, 2H, H e or H e' ), 0.86 (m, 2H, H e or H e' ); 13 C NMR (CDCl 3 , 100 MHz) ? 162, pp.4-0317 ,
48 (d, 1H, 3 J H 5 -H 7 or H 7 -H 5 = 1.8 Hz ,
R f (SiO 2 , cyclohexane/ethyl acetate, pp.179-181 ,
95 (s, 2H, H a ), 3.76 (s, 3H, H b ), 3.31 (m, 1H10 (m, 2H, H d or H d' ), 0.88 (m, 2H, H d or H d' ); 13 C NMR (CDCl 3 , 100 MHz) ? 153, pp.147-154 ,
77 (d, 1H, 3 J H 5' -H 6' = 8.4 Hz40 (d, 1H, 3 J H a -H b = 13.1 Hz, 2H, H k or H k' ); 13 C NMR (CDCl 3, pp.6602-6606 ,
06 (dd, 1H, 3 J H 6' -H 5' = 8.4 Hz, 4 J H 6' -H 2' = 2.1 Hz, pp.6-26 ,
84 (s, 3H, H i ), 3.82 (s, 3H, 4.81 (d, 1H, 2 J H d -H d' = 14.2 Hz, H d ), pp.4-4 ,
01 (d, 1H, 4 J H 2' -H 6' = 2.1 Hz77 (d, 1H, 3 J H 5' -H 6' = 8.4 Hz, H 5' ), 6.26 (d, 1H, 3 J H b -H a = 7.1 Hz, 4.98 (m, 2H, H f ), pp.4-4785812736 ,
-oxoethyl)quinoline- 4-yl]carbamate (20a) A mixture of 19a (170 mg, 0.34 mmol, 1.0 eq.) in formic acid (10 mL) was stirred at 50 o C for 20 hours After cooling to rt, the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (20 mL) before addition of a saturated aqueous sodium carbonate solution (25 mL) After decantation, the aqueous layer was then extracted with ethyl acetate (2 × 20 mL). The combined organic layers were washed with brine (60 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography, p.20 ,
89 (m, 1H, H 6'(B) ), 6.80 (d, 1H, 3 J H 5'(A) -H 6'(A) = 8.4 Hz, p.78 ,
80 (t, 2H, 3 J H a -H b = 5.8 Hz, H a ), 1.15 (m, 2H, H f or H f' ), 0.77 (m, 2H, H f or H f' ); 13 C NMR (CDCl 3 , 100 MHz) ? 154, = 5.8 Hz, H b ), 2.92 (m, 1H, H e ), pp.4-4883 ,
1H, 3 J H 6' -H 5' = 8.4 Hz, 4 J H 6' -H 2' = 2.1 Hz, H 6' ), 6.88 (d, 1H, 3 J H 5' -H 6' = 8.4 Hz, H 5' ), 4.49 (s, 2H ,
1.33 (t, 3H, 3 J H f -H e = 7.5 Hz, H f ); 13 C NMR (CDCl 3 , 100 MHz) ? 154, pp.82-148 ,
15 (dd, 1H, 3 J H 6' -H 5' = 8.5 Hz, 4 J H 6' -H 2' = 2.2 Hz, H 6' ), 7.09 (d, 1H91 (d, 1H, 3 J H 5' -H 6' = 8.5 Hz, H 5' ), 4.78 (s, 2H, pp.3192-3192 ,
32 (d, 1H, 4 J H 2' -H 6' = 2.1 Hz, pp.7-15 ,
The combined organic layers were washed with brine (2 × 40 mL), dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The crude product was purified by column chromatography (SiO 2 v/v) to give the desired product 24b (80 mg, 0.19 mmol, 29%) as a yellow solid R f (SiO 2 , cyclohexane/ethyl acetate, 6/4, v/v): 0.51; Mp: 149-151 °C; IR (cm -1 ): 2229 (? C?N ), 1505 (? C=C, °C for 30 hours. After cooling to rt, a saturated aqueous sodium hydrogen carbonate solution 7.59 (m, 1H, H 7 ), 7.34 (d, 1H, 4 J H 2' -H 6' = 2.2 Hz, pp.1260-1104, 2002. ,
CDCl 3 , 100 MHz) ? 154, p.145 ,
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