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13. General procedure: A solution of 2 (1.02 g, 2.56 mmol) in anhydrous
˚
2-propanol (50 mL) was treated with powder 4 A molecular sieves
(4.5 g), and the resulting mixture was heated to reflux under nitrogen
for 92 h. The cooled reaction mixture was filtered through a Celite
pad (washed with EtOAc, 3 ꢀ 20 mL), and the filtrate was evaporated
to give a yellow solid that was purified by flash chromatography
(SiO2, 3 ꢀ 17 cm, 60% EtOAc–hexane) to give 3 as a white solid. Mp
96–97 °C; 1H NMR (DMSO-d6, 200 MHz) d 8.68 (1H, s), 7.25–7.05
(5H, m), 5.58 (2H, t, J = 7.2 Hz), 4.48 (1H, t, J = 7.2 Hz, D2O
exchangeable), 3.48–3.33 (2H, m), 3.11 (2H, t, J = 7.2 Hz), 2.72 (2H,
t, J = 7.2 Hz), 1.86 (2H, p, J = 7.2 Hz); UV (MeOH) kmax 270
(1.43 ꢀ 10ꢁ3); HRMS calcd for C16H17N4OCl: 316.7900, found,
316.7900. Anal. Calcd for C16H17N4OCl: C, 60.66; H, 5.41; N,
17.69. Found: C, 60.38; H, 5.17; N, 17.69.
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16. Products were isolated via preparative TLC (SiO2, 50% EtOAc–
hexane). A (Z-isomer, 12% yield): 1H NMR (CDCl3, 200 MHz) d 8.18
(1H, s), 7.34–7.19 (5H, m), 5.21 (1H, br peak), 4.37 (2H, m), 3.72 (2H,
m), 2.91 (2H, t, J = 7 Hz), 2.76 (2H, t, J = 8 Hz), 2.21 (2H, m); MS:
317.3 and 319.3 (M+1). A (E-isomer, 2% yield): 1H NMR (CDCl3,
200 MHz) d 8.30 (1H, s), 7.36–7.19 (5H, m), 6.25 (1H, br peak), 4.47
(2H, t, J = 7 Hz), 3.78–3.63 (4H, m), 2.89 (2H, t, J = 7 Hz), 2.48 (2H,
m), 2.01 (2H, m); MS: 317.3 and 319.3 (M+1).
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