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A. Khalaj et al. / European Journal of Medicinal Chemistry 39 (2004) 699–705
Table 2
Spectroscopic data of 3(2H)-isothiazolones 5a–j, 5s and 6a–r
Compound 1H NMR (d)
IR (cm–1
)
Mass m/e EI (relative abundance %)
211 (20 M+), 177 (100)
5a
(CDCl3): 6.32 (d, 1H, CH, J = 4.0 Hz) 7.25–7.60 (m, 4H, Ar–H) 8.17 1660 (CO, amide)
(d, 1H, CH, J = 4.0 Hz)
(CDCl3): 6.38 (d, 1H, CH, J = 4.0 Hz) 7.8 (d, 2H, Ar–H, J = 8.0 Hz) 1671 (CO, amide); 1520, 222 (100 M+), 176 (10)
5b
8.30 (d, 2H, Ar–H, J = 8.0 Hz) 8.38 (d, 1H, CH, J = 4.0 Hz)
1342 (NO2)
5c a
(CDCl3): 1.41 (t, 3H, CH3, J = 8.0 Hz) 4.40 (q, 2H, CH2, J = 8.0 Hz) 1723 (CO, ester); 1664 249 (90 M+), 221 (35), 204 (100), 176 (30)
6.35(d, 1H, CH, J = 4.0 Hz) 7.75 (d, 2H,Ar–H, J = 8.0 Hz) 8.12 (d, 2H, (CO, amide)
Ar–H, J = 8.0 Hz) 8.20 (d, 1H, CH, J = 4.0 Hz)
5d
5e b
5f
(CDCl3): 6.33 (d, 1H, CH, J = 6.4 Hz) 7.73 (s, 4H, Ar–H) 8.19 (d, 1H, 1675 (CO, amide)
CH, J = 6.4 Hz)
(CDCl3): 6.38 (d, 1H, CH, J = 6.4 Hz) 7.20–7.50 (m, 5H, Ar–H) 8.20 1656 (CO, amide)
(d, 1H, CH, J = 6.4 Hz)
245 (100 M+)
177 (100 M+), 99 (45)
191 (100 M+), 176 (25)
(CDCl3): 2.30 (s, 3H, CH3) 6.31(d, 1H, CH, J = 6.4 Hz) 7.25 (d, 2H, 1654 (CO, amide)
Ar–H, J = 8.0 Hz) 7.43 (d, 2H, Ar–H, J = 8.0 Hz) 8.14 (d, 1H, CH,
J = 8.0 Hz)
5h
5i
(CDCl3): 1.40 (t, 3H, CH3, J = 8.1 Hz) 4.02 (q, 2H, CH2, J = 8.1 Hz) 1656 (CO, amide); 1248 221 (100 M+), 192 (80)
6.26 (d, 1H, CH, J = 6.4 Hz) 6.95 (d, 2H,Ar–H, J = 8.0 Hz) 7.44 (d, 2H, (CO, ether)
Ar–H, J = 8.0 Hz) 8.14 (d, 1H, CH, J = 6.4 Hz)
(CDCl3): 1.02 (t, 3H, CH3, J = 7.2 Hz) 1.75 (m, 2H, CH2) 3.84 (t, 2H, 1669 (CO, amide); 1246 235 (100 M+), 192 (100)
OCH2, J = 7.2 Hz) 6.28 (d, 1H, CH, J = 6.4 Hz), 6.90 (d, 2H, Ar–H, (CO, ether)
J = 8.0 Hz) 7.40 (d, 2H, Ar-H, J = 8.0 Hz) 9.14 (d, 1H, CH, J = 6.4 Hz)
5j
(CDCl3): 2.82 (s, 6H, 2NCH3) 6.30 (d, 1H, CH, J = 6.4 Hz) 7.02–7.52 1654 (CO, amide)
220 (100 M+), 191 (11), 177 (27)
(m, 4H, Ar–H) 8.18 (d, 1H, CH, J = 6.4 Hz)
5s
6a
6b
6c
(CDCl3): 6.29 (d, 1H, CH, J = 6.4 Hz) 7.27 (d, 2H, Ar–H, J = 8.0 Hz) 1644 (CO, amide)
7.47 (d, 2H, Ar–H, J = 8.0 Hz) 9.26 (d, 1H, CH, J = 6.4 Hz)
(CDCl3): 6.50 (s, 1H, CH) 7.40 (d, 2H, Ar–H, J = 8.0 Hz) 7.55 (d, 2H, 1666 (CO, amide)
Ar–H, J = 8.0 Hz)
223 (100 M+), 208 (37)
248 (8 M+2), 246 (20 M+), 211 (100)
(CDCl3): 6.40 (s, 1H, CH) 7.81 (d, 2H, Ar–H, J = 8.0 Hz) 8.30 (d, 2H, 1690 (CO, amide); 1516, 258 (41 M+2), 256 (100 M+), 210 (10)
Ar–H, J = 8.0 Hz)
1301 (NO2)
(CDCl3): 1.40 (t, 3H, CH3, J = 8.1 Hz) 4.40 (q, 2H, CH2, J = 8.1 Hz) 1725 (CO, ester); 1667 285 (45 M+2), 283 (100 M+), 255 (35),
6.37 (s, 1H, CH) 7.65 (d, 2H, Ar–H, J = 8.0 Hz) 8.15 (d, 2H, Ar–H, (CO, amide)
J = 8.0 Hz)
238 (100), 210 (18)
6d
6e c
6f
(CDCl3): 6.30 (s, 1H, CH) 7.70 (s, 4H, Ar–H)
(CDCl3): 6.30 (s, 1H, CH) 7.30–7.60 (m, 5H, Ar–H)
1678 (CO, amide)
1659 (CO, amide)
281 (36 M+2), 279 (100 M+), 244 (23)
213 (43 M+2), 211 (100 M+), 99 (56)
227 (43 M+2), 225 (100 M+), 210 (10),
190 (72)
(CDCl3): 2.37 (s, 3H, CH3) 6.35 (s, 1H, CH) 7.25 (d, 2H, Ar–H, 1661 (CO, amide)
J = 8.0 Hz) 7.36 (d, 2H, Ar–H, J = 8.0 Hz)
6g
6h
(CDCl3): 3.90 (s, 3H, CH3) 6.34 (s, 1H, CH) 6.90 (d, 2H, Ar–H, 1660 (CO, amide); 1251 243 (45 M+2), 241(100 M+), 226 (10), 190
J = 8.0 Hz) 7.45 (d, 2H, Ar–H, J = 8.0)
(CO, ether)
(10)
(CDCl3): 1.41 (t, 3H, CH3, J = 8.1 Hz) 4.01(q, 2H, CH2, J = 8.1 Hz) 1661 (CO, amide); 1254 257 (45 M+2), 255 (100 M+), 227 (42)
6.33 (s, 1H, CH) 6.90 (d, 2H, Ar–H, J = 8.0 Hz) 7.37 (d, 2H, Ar–H, (CO, ether)
J = 8.0 Hz)
6i
(CDCl3): 1.03 (t, 3H, CH3, J = 7.2 Hz) 1.68–1.94 (m, 2H, CH2) 3.92 (t, 1671 (CO, amide); 1246 271 (50 M+2), 269 (100 M+), 226 (100),
2H, OCH2, J = 7.2 Hz) 6.31 (s, 1H, CH) 6.85 (d, 2H, Ar–H, J = 8.0 Hz) (CO, ether)
192 (30)
7.36 (d, 2H, Ar–H, J = 8.0 Hz)
(CDCl3): 2.83 (s, 6H, 2NCH3) 6.34 (s, 1H, CH) 7.00–7.50 (m, 4H, 1659 (CO, amide)
6j
256 (45 M+2), 254 (100 M+)
Ar–H)
6k
6l b
(CDCl3): 2.31 (s, 3H, CH3) 6.36 (s, 1H, CH) 7.17 (d, 2H, Ar–H, 1760 (CO, ester); 1678 271 (5 M+2), 269 (10 M+), 254 (10), 226
J = 8.0 Hz) 7.53 (d, 2H, Ar–H, J = 8.0 Hz)
(CDCl3): 6.53 (s, 1H, CH) 11.2 (broad, 1H, NH)
(CO, amide)
(35), 220 (100), 191(70)
3449 (OH); 1643 (CO, 137 (41 M+2), 135 (100 M+)
amide)
6m b
6n
(CDCl3): 4.86 (s, 2H, CH2) 6.25 (s, 1H, CH) 7.31 (s, 5H, Ar–H)
1662 (CO, amide)
227 (40 M+2), 225 (100 M+)
(CDCl3): 6.26 (s, 1H, CH) 6.73 (d, 2H, Ar–H, J = 8.1 Hz) 7.18 (d, 2H, 3349 (NH, amide); 1705, 296 (9 M+2), 294 (22 M+), 252 (100), 225
Ar–H, J = 8.1 Hz) 8.06 (s, 1H, CH) 11.70 (broad, 1H, NH)
1686 (CO, amide)
(10), 210 (35), 176 (38)
6o
6p
(DMSO-d6): 2.95–3.01 (m, 4H, CH2) 3.05–3.06 (m, 4H, CH2) 6.50 (d, 3399 (NH, amide); 1648 297 (5 M+2), 295 (10 M+), 252 (100), 210
2H, Ar–H, J = 8.0 Hz) 6.70 (d, 2H, Ar–H, J = 8.0 Hz) 6.75 (s, 1H, CH) (CO, amide)
(CDCl3): 3.25–3.31 (m, 8H, CH2) 6.25 (s, 1H, CH) 6.60–7.02 (m, 9H, 1660 (CO, amide)
Ar–H)
(60)
373 (9 M+2), 371 (19 M+), 294 (28), 252
(100), 238 (50), 223 (76), 211 (28), 161
(47), 119 (40)
6q
6r
(DMSO-d6): 1.24 (t, 3H, CH3, J = 7.2 Hz) 2.90–3.60 (m, 8H, CH2) 1719 (CO, ester); 1662 369 (5 M+2), 367 (14 M+), 337 (12), 322
4.10 (q, 2H, CH2, J = 7.2 Hz) 6.26 (s, 1H, CH) 7.00–7.40 (m, 4H, (CO, amide)
(100), 252 (63), 176 (20)
Ar–H)
(DMSO-d6): 2.07–2.90 (m, 4H, CH2) 3.30–3.40 (m, 4H, CH2) 5.95 3370, 3190 (NH2, amide); 340 (11 M+2), 338 (30 M+), 294 (100),
(broad, 2H, NH2) 6.27 (d, 2H, Ar–H, J = 8.1 Hz) 6.48 (d, 2H, Ar–H, 1659 (CO, amide)
J = 8.1 Hz) 6.72 (s, IH, CH)
210 (30), 130 (15)
a Spectral data are in accordance with values given in [22].
b Spectral data are in accordance with values given in [11].
c Spectral data are in accordance with values given in [23].