HETEROCYCLES, Vol. 65, No. 5, 2005
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9.72 (br, 1H). IR (KBr) cm-1: 3354, 3215, 2931, 1676, 1635, 1591, 1485, 1458, 1418, 1365, 1257, 1166,
1061. MS m/z: 300 (M+). Anal. Calcd for C17H20N2O3: C, 67.98; H, 6.71; N, 9.33. Found C, 67.72; H,
6.75; N, 9.16.
Compound (9): yield 87%, recrystallized from DMF as yellow crystals, mp 233oC~235oC. 1H-NMR (300
MHz, δ ppm, CDCl3): 1.69 (s, 3H), 2.85 (br, 2H), 3.32 (m, 2H), 6.66 (d, J = 13.7, 1H), 6.90-7.50 (m,
10H), 10.89 (br, 1H). IR (KBr) cm-1: 3215, 2850, 1628, 1577, 1506, 1456, 1365, 1224, 1026. MS m/z:
304 (M+). Anal. Calcd for C20H20N2O: C, 78.92; H, 6.62; N, 9.20. Found C, 78.51; H, 6.62; N, 9.26
o
1
Compound (10): yield 68%, recrystallized from EtOH as yellow crystals, mp 234oC~236 C. H-NMR
(300 MHz, δ ppm, CDCl3): 3.07 (t, J = 5.94, 2H), 3.64 (t, J = 6.02, 2H), 6.38 (br, 1H), 7.06 (t, J = 7.53,
2H), 7.18 (m, 1H), 7.20 (m, 1H), 7.44 (d, J = 7.93, 1H), 7.52 (d, J = 7.70, 1H), 8.19 (br, 1H). IR (KBr)
cm-1: 3319, 3224, 2920, 2219, 2204, 1616, 1558, 1490, 1456, 1180. MS m/z: 236 (M+). Anal. Calcd for
C14H12N4: C, 71.17; H, 5.12; N, 23.71. Found C, 71.06; H, 5.10; N, 23.48.
Compound (11): yield 58% as an yellow oil. 1H-NMR (300 MHz, δ ppm, CDCl3): 3.09 (t, J = 6.31, 2H),
3.65 (m, 2H), 6.35 (d, J = 5.67, 1H), 6.50 (m, 1H), 7.05 (s, 1H), 7.14-7.28 (m, 2H), 7.40 (d, J = 8.01, 1H),
7.56 (d, J = 7.76, 1H), 8.31 (br, 1H), 9.23 (br, 1H). IR (KBr) cm-1: 3053, 2922, 2852, 1639, 1550, 1458,
1126. HRMS (EI) m/z calcd for C12H13N3O2 231.2536 (M+), found 231.2531.
Procedure for the preparation of compounds (12-16)
For 12-14: The indole derivative (7-9) (1 mmol) was dissolved in 10 mL of saturated HCl/benzene
o
solution and stirred for 30 min at 20 C. After evaporation of the solvent and recrystallization from ethyl
alcohol, the desired products were obtained. For 15, 16: To a solution of indole derivatives (10, 11) (1
mmol) in 10 mL of acetonitrile was added 1 mL of glacial acetic acid. The reaction mixture was refluxed
under nitrogen. Upon completion or after the indicated reaction time, the solvent was removed under
reduced pressure. The residue was purified by column chromatography (SiO2; EtOAc/hexane, 4:1) to give
the desired products.
Compound (12): yield 92%, recrystallized from EtOH as white crystals, 200oC (decomp). 1H-NMR (300
MHz, δ ppm, DMSO-d6): 2.29 (s, 3H), 3.06 (m, 2H), 3.29 (s, 3H), 3.51 (m, 2H), 3.65 (m, 1H), 5.07 (m,
1H), 7.05 (t, J = 7.32, 1H), 7.15 (t, J = 7.73, 1H), 7.33 (d, J = 8.1, 1H), 7.45 (d, J = 7.84, 1H), 9.67 (br,
2H). IR (KBr) cm-1: 3232, 3051, 2922, 2736, 1712, 1606, 1494, 1458, 1379, 1207, 1178. MS m/z: 307
(M+). Anal. Calcd for C16H19N2O2Cl: C, 62.64; H, 6.24; N, 9.13. Found C, 62.90; H, 6.20; N, 9.47.
Compound (13): yield 89%, recrystallized from EtOH as yellow crystals, 250oC (decomp). 1H-NMR (300
MHz, δ ppm, DMSO-d6): 2.93 (m, 2H), 3.13 (m, 1H), 3.43 (m, 1H), 3.56 (m, 1H), 3.75 (s, 3H), 5.05 (m,
1H), 7.04 (t, J = 7.47, 1H), 7.14 (t, J = 7.23, 1H), 7.37 (d, J = 8.01, 1H), 7.46 (d, J = 7.68, 1H), 9.53 (br,
2H), 11.08 (s, 1H). IR (KBr) cm-1: 3429, 3254, 3044, 2924, 2706, 1722, 1602, 1454, 1398, 1204, 1181.
MS m/z: 309 (M+). Anal. Calcd for C15H17N2O3Cl: C, 58.35; H, 5.55; N, 9.07. Found C, 58.69; H, 6.04;