S. Liu et al. / Journal of Fluorine Chemistry 105 (2000) 111±115
115
Table 2
1H NMR data of compounds IIIa±h
Compound III
1H NMR (CDCl3) d ppm
a
b
c
d
e
f
1.36 (t, 3H, CH3, J7.2 Hz), 3.77 (q, 2H, CH2, J7.2 Hz), 4.81 (s, 2H, SCH2), 7.22±8.10 (m, 4H)
1.37 (t, 3H, CH3, J7.2 Hz), 3.77 (q, 2H, CH2, J7.2 Hz), 4.80 (s, 2H, SCH2), 7.17±7.99 (m, 4H)
1.31 (t, 3H, CH3, J7.2 Hz), 3.72 (q, 2H, CH2, J7.2 Hz), 4.75 (s, 2H, SCH2), 7.11 (m, 2H), 8.14 (m, 2H)
1.33 (t, 3H, CH3, J7.2 Hz), 3.73 (q, 2H, CH2, J7.2 Hz), 4.78 (s, 2H, SCH2), 7.54 (d, 1H, J6.6 Hz), 7.78 (d, 1H, J9.4 Hz)
5.19 (s, 2H, SCH2), 7.20±7.50 (m, 8H), 8.12 (td, 1H, J7.5 Hz, J1.4 Hz)
5.21 (s, 2H, SCH2), 7.20 (m, 1H), 7.41±7.53 (m, 6H), 7.94 (m, 1H) 8.30 (dt, 1H, J7.7 Hz, J1.5 Hz)
5.18 (s, 2H, SCH2), 7.14 (t, 2H, J8.6 Hz), 7.40±7.49 (m, 5H), 8.21 (dd, 2H, J8.6 Hz, J5.5 Hz)
5.20 (s, 2H, SCH2), 7.38±7.50 (m, 5H), 7.58 (d, 1H, J6.7 Hz), 7.83 (d, 1H, J9.3 Hz)
g
h
Table 3
IR and MS spectral data of compounds IIIa±h
1
)
Compound III IR (KBr) (cm
EI MS m/e (%)
a
b
c
d
e
f
3020, 2990, 1715, 1615, 1585, 1520, 1500, 1410, 1320, 1190,
1065, 795
278 (86, M ), 207 (58), 165 (39), 149 (12), 121 (81), 86 (100),
57 (65)
2990, 1715, 1615, 1590, 1525, 1500, 1470, 1415, 1310,
1265, 1205, 1180, 875, 790, 740
278 (100, M ), 207 (46), 165 (43), 149 (26), 121 (73), 86 (47),
57 (49), 56 (14)
3010, 2990, 1710, 1605, 1495, 1475, 1415, 1320, 1275, 1215,
845, 745
278 (100, M ), 207 (48), 165 (43), 149 (28), 121 (82), 86 (40),
57 (42)
3010, 2990, 1715, 1600, 1505, 1490, 1470, 1455, 1405, 1335,
1090, 890, 725
350 (5, M 4), 348 (23, M 2), 346 (38, M ), 277 (11),
275 (16), 240 (12), 191 (23), 189 (34), 86 (100), 57 (58), 56 (16)
3020, 2950, 1730, 1620, 1580, 1520, 1490, 1440, 1390, 1210, 1060, 326 (60, M ), 207 (48), 165 (4), 149 (10), 121 (19), 105 (100),
770, 760, 740
3020, 1732, 1590, 1520, 1495, 1425, 1350, 1210, 1060, 870, 740
104 (40), 86 (40), 77 (17), 57 (45)
326 (52, M ), 207 (30), 165 (3), 149 (16), 121 (30), 105 (100),
104 (39), 86 (28), 77 (35), 57 (54)
g
h
3040, 1730, 1605, 1490, 1430, 1380, 1220, 1070, 850, 750
326 (95,M ), 205 (39), 165 (5), 149 (26), 121 (38), 105 (100),
104 (39), 86 (20), 77 (43), 57 (57)
3050, 1735, 1595, 1495, 1450, 1390, 1315, 1270, 1210, 1090, 1060, 395 (68, M 1), 397 (44), 276 (11), 241 (13), 191 (10),
950, 890, 725
189 (15), 105 (100), 104 (46), 86 (27), 57 (29), 50 (14)
[9] S.Y. Liu, X.H. Qian, J. Chen and G.H. Song, Novel fused
heterocycles: synthesis and activities of 5,6-dihydro-7-thia-1,3,3a,5-
tetraaza-inden-4-ones and 1-thia-3,4a,9-triaza-fluoren-4-ones deriva-
tives, Monatshefte fur Chemie, in press.
Acknowledgements
This study was ®nancially supported by Shanghai Foun-
dation of Science and Technology.
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[11] H. Ulrich, R. Richter, P.J. Whitman, A.A.R. Sayigh, J. Org. Chem. 39
(1974) 2897.
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