970
H. Qian and Y. Lian
(400 MHz, CDCl3): d ¼ 3.16 (d, J, 7.41 Hz, 2H), 3.79–3.89 (m, 3H), 5.08
(s, 1H), 7.03 (m, 1H), 7.10–7.12 (m, 2H), 7.26–7.29 (m, 5H), 7.50–7.52
(m, 2H). 13C NMR (CDCl3): d ¼ 31.81, 47.95, 54.38, 120.79, 122.87,
127.14, 128.28, 128.48, 128.84, 132.89, 146.51, 160.53. MS (EI, 70 eV):
m/z ¼ 348 (Mþ), 267, 245,191,157, 131, 77, 73. Anal. calcd. for
C16H16N2SSe: C, 55.33; H, 4.54; N, 8.07. Found: C, 55.41; H, 4.59; N, 8.10.
Compound 2b. Yield 97%; IR (KBr): 3440, 3062, 2921, 2853, 1649, 1595,
1
1477, 1214, 738 cm21. H NMR (400 MHz, CDCl3): d ¼ 2.32 (s, 3H), 3.16
(d, J, 7.06 Hz, 2H), 3.62 (d, J, 8.20 Hz, 1H), 3.71–3.78 (m, 2H), 7.02–7.05
(m, 2H), 7.14–7.20 (m, 2H), 7.29 (m, 3H), 7.51 (m, 2H), 7.69 (s, 1H). 13C
NMR (CDCl3): d ¼ 18.04, 32.23, 47.63, 52.97, 122.22, 123.99, 126.49,
127.66, 129.43, 130.40, 130.60, 133.40, 135.72, 147.40, 161.83. MS (EI,
70 eV): m/z ¼ 363 (Mþ), 347, 281, 249, 205, 189,157, 91, 77, 73. Anal.
calcd. for C17H18N2SSe: C, 56.50; H, 5.02; N, 7.75. Found: C, 56.59; H,
4.96; N, 7.81.
Compound 2c. Yield 96%; yellow solid; mp 142–1438C. IR (KBr): 3419,
3027, 2923, 2860, 1635, 1603, 1523, 1477, 1350, 1193, 737 cm21. 1H NMR
(400 MHz, CDCl3): d ¼ 3.18 (d, J, 7.53 Hz, 2H), 3.69–3.72 (m, 1H),
3.78–3.82 (m, 1H), 3.85–3.90 (m, 1H), 5.92 (s, 1H), 7.27–7.33 (m, 4H),
7.42 (m, 1H), 7.52 (d, J, 7.30 Hz, 2H), 7.89 (d, J, 1.87 Hz, 2H). 13C NMR
(CDCl3): d ¼ 31.93, 48.08, 52.46, 116.37, 117.95, 121.20, 127.79,127.86,
128.42, 129.43, 129.62, 133.56, 148.80, 150.01, 162.01. MS (EI, 70 eV):
m/z ¼ 393 (Mþ), 288, 236, 222, 180, 134, 90, 73. Anal. calcd. for
C16H15N3O2SSe: C, 48.98; H, 3.85; N, 10.71. Found: C, 48.90; H, 3.79; N,
10.69.
Compound 2d. Yield 92%; IR (KBr): 3432, 3260, 3052, 2926, 2855, 1636,
1
1508, 1384, 1242, 1033, 739 cm21. H NMR (400 MHz, CDCl3): d ¼ 3.15
(d, J, 6.62 Hz, 2H), 3.71–3.83 (m, 3H), 3.77 (s, 3H), 6.82 (d, J, 8.63 Hz,
2H), 7.00 (d, J, 8.16 Hz, 2H), 7.27–7.32 (m, 3H), 7.50 (m, 2H), 7.58
(s, 1H). 13C NMR (CDCl3): d ¼ 32.30, 48.29, 54.53, 55.46, 144.19, 122.78,
124.63, 127.66, 128.74, 129.44, 133.38, 135.80, 140.27, 156.00, 161.49. MS
(EI, 70 eV): m/z ¼ 378 (Mþ), 313, 297, 254, 221, 155,122, 77, 73. Anal.
calcd. for C17H18N2OSSe: C, 54.11; H, 4.81; N, 7.42. Found: C, 54.02; H,
4.75; N, 7.44.
Compound 2e. Yield 94%; IR (KBr): 3419, 3157, 3068, 2922, 2860, 1638,
1
1581, 1477, 1193, 736 cm21. H NMR (400 MHz, CDCl3): d ¼ 3.16 (d, J,
6.32 Hz, 2H), 3.75 (m, 1H), 3.82 (d, J, 6.32 Hz, 2H), 6.58 (s, 1H), 6.97–
7.01(t, J, 7.64 Hz,1H), 7.17–7.21 (t, J, 7.75 Hz, 1H), 7.26–7.30 (m, 4H),
7.36 (d, J, 7.96 Hz, 1H), 7.50 (m, 2H). 13C NMR (CDCl3): d ¼ 32.13,
48.19, 54.16, 122.77, 123.33, 124.03, 126.12, 127.37, 127.74, 128.69,
129.35, 129.50, 133.47, 145.14, 161.58. MS (EI, 70 eV): m/z ¼ 383 (Mþ),
345, 301, 225, 189,157, 91, 73. Anal. calcd. for C16H15ClN2SSe: C, 50.34;
H, 3.96; N, 7.34. Found: C, 50.27; H, 3.88; N, 7.38.