3832
C. Deng et al. / Tetrahedron 68 (2012) 3828e3834
(d, J¼8.8 Hz, 2H), 6.88 (d, J¼9.2 Hz, 2H), 6.05 (s, 1H), 3.86 (s, 3H),
3.85 (s, 3H); 13C NMR (CDCl3, 100 MHz):
(ppm) 190.4, 189.5, 164.3,
911, 862, 755, 692, 554; HRMS (ESI): m/z [MþH]þ calcd for
d
C30H21NO2: 428.1645; found: 428.1636.
162.5, 156.3, 138.7, 132.0, 131.5, 129.2, 129.0,127.4, 124.4,121.1,113.9,
113.5, 94.4, 55.3, 55.1; IR (KBr, cmꢁ1): 2927, 2835, 1657, 1594, 1510,
1456, 1420, 1314, 1247, 1169, 1060, 1030, 912, 847, 793, 758, 696,
626, 554; HRMS (ESI): m/z [MþH]þ calcd for C24H21NO4: 388.1543;
found: 388.1549.
4.5.8. (Z)-1,4-Di(furan-2-yl)-2-(phenylamino)but-2-ene-1,4-dione
(3ia). Yield 96%, red solid, mp 53e55 ꢀC; 1H NMR (CDCl3,
400 MHz): d (ppm) 12.05 (s, 1H), 7.61 (s, 1H), 7.55 (s, 1H), 7.30e7.16
(m, 4H), 7.04 (t, J¼7.2 Hz, 1H), 6,98 (d, J¼8.0 Hz, 2H), 6.51 (d,
J¼7.8 Hz, 2H), 6.13 (s, 1H); 13C NMR (CDCl3, 100 MHz):
d (ppm)
4.5.3. (Z)-1,4-Bis(4-chlorophenyl)-2-(phenylamino)but-2-ene-1,4-
179.7, 178.4, 155.0, 153.3, 150.5, 148.5, 145.5, 138.7, 129.2, 124.8,
122.1, 121.3, 115.0, 112.6, 112.3, 95.7; IR (KBr, cmꢁ1): 3123, 1659,
1575, 1460, 1389, 1272, 1229, 1156, 1070, 1026, 917, 881, 757, 693,
590, 557; HRMS (ESI): m/z [MþH]þ calcd for C18H13NO4: 308.0917;
found: 308.0922.
dione (3da).6 Yield 89%, yellow solid, mp 162e164 ꢀC; 1H NMR
(CDCl3, 400 MHz):
d
(ppm) 12.51 (s, 1H), 7.88 (q, J¼8.4 Hz, 4H), 7.41
(d, J¼8.4 Hz, 2H), 7.35 (d, J¼8.4 Hz, 2H), 7.16 (t, J¼7.6 Hz, 2H), 7.01 (t,
J¼7.4 Hz, 1H), 6.96 (d, J¼8.0 Hz, 2H), 6.06 (s, 1H); 13C NMR (CDCl3,
100 MHz):
d (ppm) 190.9, 189.6, 156.6, 140.9, 138.3, 137.1, 132.8,
130.8, 129.3, 129.1, 128.7, 125.4, 121.8, 94.6; IR (KBr, cmꢁ1): 1667,
1575, 1505, 1398, 1279, 1235, 1170, 1085, 1011, 913, 845, 757, 692,
536; HRMS (ESI): m/z [MþH]þ calcd for C22H15Cl2NO2: 396.0553;
found: 396.0560.
4.5.9. (Z)-2-(Phenylamino)-1,4-di(thiophen-2-yl)but-2-ene-1,4-
dione (3ja). Yield 98%, tan solid, mp 127e128 ꢀC; 1H NMR (CDCl3,
400 MHz):
d
(ppm) 12.12 (s, 1H), 7.81 (d, J¼3.6 Hz, 1H), 7.71 (d,
J¼4.8 Hz, 1H), 7.66 (d, J¼3.6 Hz, 1H), 7.59 (d, J¼5.2 Hz, 1H), 7.20 (t,
J¼7.6 Hz, 2H), 7.12 (t, J¼8.0 Hz, 1H), 7.08 (t, J¼4.2 Hz, 1H), 7.04e6.99
4.5.4. (Z)-1,4-Bis(4-bromophenyl)-2-(phenylamino)but-2-ene-1,4-
(m, 3H), 6.08 (s, 1H); 13C NMR (CDCl3, 100 MHz):
d (ppm) 183.6,
dione (3ea).16 Yield 90%; light yellow solid; mp 163e164 ꢀC; 1H
183.5, 155.3, 145.7, 141.4, 138.6, 136.3, 135.6, 132.3, 129.6, 129.2,
129.0, 128.4, 128.0, 124.8, 121.1, 118.1, 114.8, 95.6; IR (KBr, cmꢁ1):
3092, 1646, 1581, 1506, 1410, 1349, 1295, 1249, 1059, 1005, 854, 792,
738, 692, 538; HRMS (ESI): m/z [MþH]þ calcd for C18H13NO2S2:
340.0460; found: 340.0457.
NMR (CDCl3, 400 MHz):
d
(ppm) 12.49 (s,1H), 7.80 (d, J¼8.0 Hz, 4H),
7.59 (d, J¼7.6 Hz, 2H), 7.54 (d, J¼7.6 Hz, 2H), 7.17 (t, J¼7.6 Hz, 2H),
7.03 (t, J¼7.2 Hz, 1H), 6.96 (d, J¼8.0 Hz, 2H), 6.04 (s, 1H); 13C NMR
(CDCl3, 100 MHz):
d (ppm) 191.1, 189.7, 156.6, 138.3, 137.6, 133.3,
132.2, 131.8,130.9, 130.0,129.9,129.4,129.0,127.0,125.5, 121.9, 94.6;
IR (KBr, cmꢁ1): 1671, 1574, 1504, 1395, 1278, 1236, 1172, 1069, 1008,
790, 756, 692; HRMS (ESI): m/z [MþH]þ calcd for C22H15Br2NO2:
483.9542; found: 485.9514.
4.5.10. (Z)-2-((4-Chlorophenyl)amino)-1,4-diphenylbut-2-ene-1,4-
dione (3ab).6 Yield 81%, yellow solid, mp 153e155 ꢀC; 1H NMR
(CDCl3, 600 MHz):
(d, J¼7.2 Hz, 2H), 7.58 (t, J¼7.2 Hz, 1H), 7.52 (t, J¼7.5 Hz, 1H), 7.44 (q,
J¼7.8 Hz, 4H), 7.12 (d, J¼9.0 Hz, 2H), 6.91 (d, J¼9.0 Hz, 2H), 6.14 (s,
d
(ppm) 12.51 (s, 1H), 7.97 (d, J¼7.2 Hz, 2H), 7.93
4.5.5. (Z)-1,4-Bis(4-nitrophenyl)-2-(phenylamino)but-2-ene-1,4-
dione (3fa). Yield 91%, yellow solid, mp 224.6e225 ꢀC; 1H NMR
1H); 13C NMR (CDCl3, 150 MHz):
d (ppm) 191.8, 191.0, 156.1, 138.6,
(CDCl3, 400 MHz):
d
(ppm) 12.52 (s, 1H), 8.32 (d, J¼8.4 Hz, 2H), 8.20
137.3, 134.5, 134.4, 132.1, 130.3, 129.6, 129.3, 128.8, 128.4, 127.3,
122.8, 95.51, 95.48; IR (KBr, cmꢁ1): 3060, 1668, 1598, 1581, 1556,
1501, 1447, 1320, 1282, 1238, 1171, 1080, 1060, 1024, 1008, 980, 909,
852, 819, 763, 725, 703, 686, 653, 557, 540, 496; HRMS (ESI): m/z
[MþH]þ calcd for C22H16ClNO2: 362.0942; found: 362.0937.
(d, J¼8.0 Hz, 2H), 8.10 (d, J¼8.4 Hz, 2H), 8.03 (d, J¼8.4 Hz, 2H), 7.18
(t, J¼7.4 Hz, 2H), 7.05 (t, J¼7.2 Hz, 1H), 6.98 (d, J¼8.0 Hz, 2H), 6.18 (s,
1H); 13C NMR (DMSO-d6, 100 MHz):
d (ppm) 190.9, 185.1, 150.0,
149.2, 143.0, 139.8, 138.4, 130.9, 130.0, 129.9, 129.8, 129.7, 129.5,
129.3, 129.2, 129.0, 128.8, 125.9, 124.3, 124.2, 123.81, 123.76, 123.0,
122.96, 122.92; IR (KBr, cmꢁ1): 1675, 1587, 1558, 1522, 1348, 1281,
1230, 1175, 1109, 1067, 1012, 857, 800, 757, 718; HRMS (ESI): m/z
[MþH]þ calcd for C22H15N3O6: 418.1034; found: 418.1039.
4.5.11. (Z)-2-((4-Hydroxyphenyl)amino)-1,4-diphenylbut-2-ene-1,4-
dione (3ac). Yield 96%, red solid, mp 177e179 ꢀC; 1H NMR (CDCl3,
400 MHz):
2H), 7.45e7.38 (m, 4H), 6.80 (d, J¼8.4 Hz, 2H), 6.62 (d, J¼8.8 Hz, 2H),
6.41(s, 1H), 6.05(s, 1H); 13C NMR (CDCl3, 100 MHz):
(ppm) 192.5,
d (ppm) 12.38 (s, 1H), 7.94e7.89 (m, 4H), 7.57e7.48 (m,
4.5.6. (Z)-1,4-Di(naphthalen-1-yl)-2-(phenylamino)but-2-ene-1,4-
d
dione (3ga). Yield 88%, yellow solid, mp 160e162 ꢀC; 1H NMR
191.0,158.0,153.9,138.8,134.5,134.4,131.9,131.1,129.7,128.8,128.5,
127.3, 124.2, 116.2, 93.8; IR (KBr, cmꢁ1): 3458, 3436, 2974, 2927,
2372, 1666, 1598, 1571, 1513, 1446, 1405, 1386, 1323, 1302, 1278,
1236, 1167, 1065, 984, 913, 759, 711, 554; MS (EI): m/z 343.17.
(CDCl3, 600 MHz):
d
(ppm) 12.56 (s, 1H), 8.88 (d, J¼9.0 Hz, 1H), 8.61
(d, J¼8.4 Hz, 1H), 8.19 (d, J¼7.2 Hz, 1H), 7.99 (d, J¼8.4 Hz, 1H), 7.91
(d, J¼8.4 Hz, 1H), 7.86 (d, J¼7.8 Hz, 1H), 7.83 (d, J¼8.4 Hz, 1H), 7.77
(d, J¼7.2 Hz, 1H), 7.64 (t, J¼7.8 Hz, 1H), 7.57 (t, J¼7.8 Hz,
1H),7.55e7.50 (m, 2H), 7.46 (q, J¼7.5 Hz, 2H), 7.10e7.06 (m, 4H),
6.89 (t, J¼6.6 Hz, 1H), 6.06 (s, 1H); 13C NMR (CDCl3, 150 MHz):
4.5.12. (Z)-2-((4-Aminophenyl)amino)-1,4-diphenylbut-2-ene-1,4-
dione (3ad). Yield 90%, red solid, mp 148e150 ꢀC; 1H NMR (CDCl3,
d
(ppm) 195.1, 193.4, 157.4, 138.6, 138.4, 133.8, 133.7, 132.7, 131.3,
400 MHz):
2H), 7.44e7.36 (m, 4H), 6.78 (d, J¼8.4 Hz, 2H), 6.42 (d, J¼8.4 Hz, 2H),
6.02 (s, 1H), 3.59 (br s, 2H); 13C NMR (CDCl3, 100 MHz):
(ppm)
d (ppm) 12.47(s, 1H), 7.94e7.91 (m, 4H), 7.51e7.46 (m,
130.8, 130.1, 129.1, 128.8, 127.1, 126.8, 126.6, 126.5, 126.2, 125.8,
125.7, 125.4, 125.0, 124.6, 124.2, 124.1, 121.8, 100.5; IR (KBr, cmꢁ1):
3045, 1658, 1584, 1556, 1502, 1339, 1278, 1249, 1115, 984, 910, 786,
749, 697, 569; HRMS (ESI): m/z [MþH]þ calcd for C30H21NO2:
428.1645; found: 428.1637.
d
192.5, 191.3, 157.8, 153.9, 144.3, 139.0, 134.5, 134.2, 131.6, 129.5,
128.6, 128.3, 127.2, 123.9, 115.4, 93.1; IR (KBr, cmꢁ1): 3466, 3439,
3366, 3346, 3057, 1672, 1593, 1571, 1517, 1447, 1385, 1323, 1279,
1237, 1173, 1061, 1025, 984, 911, 825, 760, 713, 690, 551, 506; MS
(EI): m/z 342.22.
4.5.7. (Z)-1,4-Di(naphthalen-2-yl)-2-(phenylamino)but-2-ene-1,4-
dione (3ha). Yield 92%, red oil, 1H NMR (CDCl3, 400 MHz):
d (ppm)
12.74 (s, 1H), 8.57 (s, 1H), 8.50 (s, 1H), 8.07e8.04 (m, 2H), 7.93e7.82
(m, 5H), 7.61e7.48 (m, 3H), 7.12 (t, J¼7.8 Hz, 2H), 7.05 (d, J¼7.6 Hz,
2H), 6.94 (t, J¼7.2 Hz, 1H), 6.35 (s, 1H); 13C NMR (CDCl3, 100 MHz):
4.5.13. (Z)-Ethyl
4-((1,4-dioxo-1,4-diphenylbut-2-en-2-yl)amino)
benzoate (3ae). Yield 45%, yellow oil, 1H NMR (CDCl3, 400 MHz):
d
(ppm) 12.63(s, 1H), 8.01(d, J¼7.6 Hz, 2H), 7.94 (d, J¼7.6 Hz, 2H),
d
(ppm) 191.9, 190.5, 156.7, 138.5, 136.0, 135.8, 134.8, 132.5, 132.0,
7.84 (d, J¼8.0 Hz, 2H), 7.59e7.51 (m, 3H), 7.47e7.42 (m, 3H), 6.99 (d,
J¼8.4 Hz, 2H), 6.21(s, 1H), 4.29 (d, J¼6.8 Hz, 2H), 1.32 (t, J¼7.0 Hz,
131.8, 129.6, 129.3, 129.2, 129.1, 128.7, 128.3, 128.1, 127.7, 127.6, 127.5,
126.8, 126.3, 124.8, 123.9, 123.6, 121.4, 95.2; IR (KBr, cmꢁ1): 3054,
1732, 1667, 1569, 1501, 1465, 1355, 1285, 1238, 1185, 1122, 1047, 950,
3H); 13C NMR (CDCl3, 100 MHz):
d (ppm) 191.8, 191.3, 165.7, 155.1,
142.6, 138.5, 134.9, 134.8, 134.6, 134.3, 132.3, 131.2, 130.9, 129.7,