Table 1
Physical properties and spectral data of 3aꢀ
/
o
Compound
R
Molecular formu- M.p. (8C) UV, lmax (nm)
la (yield %)
IR (n, cmꢁ1
)
1H-NMR (DMSO-d6), (d, ppm)
3a a
5-nitro-2-furyl C18H11F2N3O5
242ꢀ
(83)
/
245
369, 280, 251,
205
3090 (Arꢀ
/
OH, NH), 1662 (CÄ
/
O), 7.09 (d, 1H, H5, Jꢂ
3.1 Hz), 7.33 (t, 1H, H11, Jꢂ
H12 Jꢂ8.7 Hz), 7.75 (d, 1H, H15, Jꢂ
CHÄN), 11.09ꢀ12.66 (2s, 2H, diflunisal OH and CONHNÄ
O), 7.09 (d, 1H, H5, Jꢂ8.6 Hz), 7.21 (t, 1H, H9, Jꢂ8.5 Hz), 7.38 (t, 1H, H11, Jꢂ
8.8 Hz), 7.47ꢀ7.77 (m, 7H,ArꢀH), 8.04 (s, 1H, H2), 8.48 (s, 1H, CHÄN), 11.91
(s, 1H, diflunisal OH), 12.02 (b, 1H, CONHNÄCH).
O), 7.09 (d, 1H, H5, Jꢂ8.5 Hz), 7.20 (t, 1H, H9, Jꢂ8.4 Hz), 7.23 (t, 1H, H11, Jꢂ
F), 1074 8.4 Hz), 7.30ꢀ7.72 (m, 6H,ArꢀH), 8.02 (s, 1H, H2), 8.44 (s, 1H, CHÄN), 11.95
(s, 2H, diflunisal OH and CONHNÄCH)
O), 7.09 (d, 1H, H5, Jꢂ8.6 Hz), 7.20 (t, 1H, H9, Jꢂ
F), 1092 8.4 Hz), 7.54 (d, 2H, H14,18, Jꢂ8.4 Hz), 7.58 (d, 1H, H6, Jꢂ
1H, H12, Jꢂ8.4 Hz), 7.78 (d, 2H, H15,17, Jꢂ8.4 Hz), 8.03 (s, 1H, H2), 8.46 (s,
1H, CHÄN), 11.95 (s, 2H, diflunisal OH and CONHNÄCH).
OH), 3125 (NH), 1652 7.09 (d, 1H, H5, Jꢂ8.5 Hz), 7.23 (t, 1H, H9, Jꢂ8.5 Hz), 7.39 (t, 1H, H11, Jꢂ
O), 1138 (ArꢀF), 1099 (Arꢀ 9 Hz), 7.54ꢀ8.06 (m, 6H, ArꢀH), 8.80 (s, 1H, CHÄN), 11.87 (b, 1H, diflunisal
OH), 12.15 (s, 1H, CONHNÄCH).
O), 7.09 (d, 1H, H5, Jꢂ8.6 Hz), 7.20 (t, 1H, H9, Jꢂ
H), 8.03 (s, 1H, H2), 8.71 (s, 1H, CHÄN), 12.00 (b, 2H, diflunisal OH and
CONHNÄCH)
O), 7.09 (d, 1H, H5, Jꢂ
ArꢀH), 8.03 (s, 1H, H2), 8.47 (s, 1H, CHÄ
OH and CONHNÄCH)
OH), 3261(NH), 7.09 (d, 1H, H5, Jꢂ8.5 Hz), 7.20 (t, 1H, H9, Jꢂ
O), 1605 (CÄN), 1149 ArꢀH), 8.03 (s, 1H, H2), 8.46 (s, 1H, CHÄN), 11.79ꢀ
OH and CONHNÄCH).
6.92ꢀ6.97 (m, 2H, ArꢀH), 7.10 (d, 1H, H5, Jꢂ
F). 8.5 Hz), 7.30ꢀ7.64 (m, 5H, ArꢀH), 8.05 (s, 1H, H2), 8.70 (s, 1H, CHÄ
11.16 (s, 1H, ArꢀOH), 11.86ꢀ12.07 (b, 2H, diflunisal OH and CONHNÄ
OH), 3150 (NH), 1647 6.86 (d, 2H, H15 17, Jꢂ8.6Hz), 7.07 (d, 1H, H5, Jꢂ8.6 Hz), 7.22 (t, 1H, H9,
O), 1612 (CÄN), 1142 (ArꢀF). Jꢂ8.4 Hz), 7.38 (t, 1H, H11, Jꢂ8.9 Hz), 7.58ꢀ7.64 (m, 4H, H6, H12 and
H14 18 N), 10.00 (s, 1H, ArꢀOH), 11.76 (s,
), 8.04 (s, 1H, H2), 8.36 (s, 1H, CHÄ
1H, diflunisal OH), 12.17 (b, 1H, CONHNÄCH)
O), 2.35 (s, 3H, CH3), 7.08 (d, 1H, H5, Jꢂ8.6 Hz), 7.21 (t, 1H, H9, Jꢂ
7.28 (d, 2H, H15 17, Jꢂ8 Hz), 7.38 (t, 1H, H11, Jꢂ8.9 Hz), 7.57ꢀ7.62 (m, 2H,
ArꢀH), 7.64 (d, 2H, H14 18, Jꢂ8 Hz), 8.02 (s, 1H, H2), 8.42 (s, 1H, CHÄN),
11.83 (s, 1H, diflunisal OH), 11.88ꢀ12.18 (b, 1H, CONHNÄCH)
O), 3.83 (s, 3H, OCH3), 7.04 (d, 2H, H15 17, Jꢂ8.6 Hz), 7.08 (d, 1H, H5, Jꢂ
Hz), 7.23 (t, 1H, H9, Jꢂ8.5 Hz), 7.38 (t, 1H, H11, Jꢂ9 Hz), 7.58ꢀ7.64 (m,
2H, H6 and H12), 7.70 (d, 2H, H14 18, Jꢂ8.6 Hz), 8.04 (s, 1H, H2), 8.42 (s, 1H,
CHÄN), 11.08ꢀ12.97 (b,2H, diflunisal OH and CONHNÄCH).
/
8.5 Hz), 7.18 (t, 1H, H9, Jꢂ
8.1 Hz), 7.56 (d, 1H, H6 Jꢂ
3.7 Hz), 7.95 (s, 1H, H2), 8.42 (s, 1H,
CH).
/
8.4 Hz), 7.25 (d, 1H, H14, Jꢂ
/
1602 (CÄN), 1144 (Arꢀ
/
/F).
/
/
9 Hz), 7.60 (d, 1H,
/
/
/
/
/
3b
C6H5
C20H14F2N2O2
250ꢀ
/
254
276
273
331, 305, 296,
251, 221, 205
3259 (Arꢀ
/
OH, NH), 1643 (CÄ
/
/
/
/
(80)
1612 (CÄN), 1142 (Arꢀ
/
/F).
/
/
/
/
3c
ꢀ/
C6H4 ꢀ/Br(4)
C20H13BrF2N2O2 275ꢀ
/
332, 307, 296,
254, 226, 203,
193
3250 (Arꢀ
1614 (CÄN), 1140 (Arꢀ
(ArꢀBr).
3252 (Arꢀ
1625 (CÄN), 1142 (Arꢀ
(ArꢀCl).
/
OH, NH), 1645 (CÄ
/
/
/
/
(78)
/
/
/
/
/
/
/
3d b
ꢀ/
C6H4 ꢀ/Cl(4)
C20H13ClF2N2O2 271ꢀ
/
331,307, 297,
223, 202, 194.
/
OH, NH), 1645 (CÄ
/
/
/8.4 Hz), 7.23 (t, 1H, H11, Jꢂ
/
(77)
/
/
/
/8.3 Hz), 7.62 (d,
/
/
/
/
/
3e
3f
3g
3h
3i
ꢀ/
C6H3 ꢀ/Cl2(2, C20H12Cl2F2N2O2 255ꢀ
/
257
262
260
265
291
271
386, 305, 234,
229, 213, 195
3250 (Arꢀ
(CÄ
Cl).
3260 (Arꢀ
1614 (CÄN), 1145 (Arꢀ
/
/
/
/
4)
(87)
/
/
/
/
/
/
/
ꢀ
/
C6H4 ꢀ
/
F(2)
F(3)
F(4)
C20H13F3N2O2
C20H13F3N2O2
C20H13F3N2O2
260ꢀ
/
329, 307, 294,
203
/
OH, NH), 1643 (CÄ
/
/
/8 Hz), 7.29ꢀ/7.99 (m, 7H, Arꢀ
/
(77)
/
/F).
/
/
ꢀ/
C6H4 ꢀ
/
259ꢀ
/
331, 306, 292,
254, 203
3263 (Arꢀ
/
OH, NH), 1641 (CÄ
/
/8.6 Hz), 7.20 (t, 1H, H9, Jꢂ/8.4 Hz), 7.22ꢀ/7.68 (m, 7H,
(78)
1614 (CÄN), 1140 (Arꢀ
/
/F).
/
/
N), 11.98ꢀ/12.17 (s, 2H, diflunisal
/
ꢀ/
C6H4 ꢀ
/
263ꢀ
/
328, 304, 292,
219, 203
3600ꢀ
1641 (CÄ
(ArꢀF).
3200ꢀ3175 (Arꢀ
(CÄO), 1616 (CÄ
/3400 (Arꢀ
/
/
/8.5 Hz), 7.30ꢀ/7.84 (m, 7H,
(73)
/
/
/
/
/
11.98 (b, 2H, diflunisal
/
/
ꢀ/
C6H4 ꢀ/OH(2) C20H14F2N2O3
290ꢀ
/
367, 358, 328,
298, 287, 237,
202
/
/
OH, NH), 1630
N), 1139 (Arꢀ
/
/
/
8.6 Hz), 7.22 (t, 1H, H9, Jꢂ
N),
CH).
/
(88)
/
/
/
/
/
/
/
/
/
3j
ꢀ/
C6H4 ꢀ/OH(4) C20H14F2N2O3
268ꢀ
/
326, 256, 229,
204
3323 (Arꢀ
/
,
/
/
(76)
(CÄ
/
/
/
/
/
/
,
/
/
/
3k
3l
ꢀ/
C6H4 ꢀ
/
C21H16F2N2O2
266ꢀ
/
268.5 371, 305, 227,
215, 202, 195
3248 (Arꢀ
/
OH, NH), 1643 (CÄ
/
/
/8.4 Hz),
CH3(4)
(88)
1612 (CÄN), 1140 (Arꢀ
/
/F).
,
/
/
/
/
,
/
/
/
/
ꢀ/
C6H4 ꢀ
/
C21H16F2N2O3
242ꢀ
/
245
366, 319, 307,
228, 200
3257(Arꢀ
/
OH, NH), 1639 (CÄ
/
,
/
/
8.6
OCH3(4)
(84)
1608 (CÄN), 1170 (Arꢀ
/
/F).
/
/
/
,
/
/
/
/