Article
Hu et al.
lute ethanol was stirred for 30 min at room temperature. The crude
product was washed with ether and recrystallized from ethanol to
provide the solid 4.
2H, J = 8.8 Hz, ArH), 6.77-6.80 (m, 2H, ArH), 4.51 (s, 2H, CH
2
);
CO),
172.2 (COO), 156.3 (PhCF), 155.2 (CH), 144.4 (PhCNH), 115.9
(2C, 2 ´ PhCH), 115.4 (2C, 2 ´ PhCH), 91.0 (CH=C), 71.1 (CH );
Z-isomer: 193.9 (CH CO), 172.2 (COO), 158.7(PhCF), 155.2
1
3
6 2
C NMR (101 MHz, DMSO-d ) d: E-isomer: 193.9 (CH
Synthesis of the title compounds 5a-5k: The intermediate
2
4
(2.5 mmol) was reacted with substituted phenylhydrazine hy-
2
drochloride (2.5 mmol) at room temperature for 3-6 h, respec-
tively. The reaction was monitored by TLC (ethyl acetate:light
petroleum:methanol:acetic acid = 10:2:2:0.2, V/V). The precipi-
(CH), 144.4 (PhCNH), 116.1 (2C, 2 ´ PhCH), 115.5 (2C, 2 ´
+
); MS m/z (EI): 236.2 (M) ; Anal.
PhCH), 89.8 (CH=C), 71.1 (CH
Calcd. for C11 FN
2
H
9
2
O
3
(236.20): C, 55.93; H, 3.84; N, 11.86.
tate was filtered, washed with water, dried over MgSO
4
and con-
Found: C, 55.80; H, 3.83; N, 11.89. Data for 5d: Light purple
powder, yield 48.1%, mp 176.5-177.9 °C; IR (KBr) v: 3343, 3238,
centrated in vacuo to give the desired products 5a-5k.
-1 1
3031, 2929, 1733, 1632, 1578, 1475, 1293, 1032, 743 cm ; H
Data for 4: Yellow powder, yield 52.6%, mp 147.7-148.6
C; IR (KBr) v: 3039, 2978, 1729, 1604, 1420, 1393, 1256, 1038,
°
NMR (400 MHz, DMSO-d ) d: 11.06 (s, 1H, ArNHNH), 8.80 (s,
6
-1 1
59 cm ; H NMR (400 MHz, DMSO-d
7
4
6
) d: 7.53 (s, 1H, CH=C),
1H, ArNHNH), 7.84 (s, 1H, CH=C), 7.37 (d, 1H, J = 7.8 Hz,
ArH), 7.25 (t, 1H, J = 7.7 Hz, ArH), 6.90 (t, 1H, J = 7.6 Hz, ArH),
1
3
.36 (s, 2H, CH
2
), 3.66 (s, 3H, NCH
) d: 191.1 (CH
3
), 3.39 (s, 3H, NCH
CO), 174.9 (COO), 156.6
); 44.1 (CH ); MS (EI)
3
); C
1
3
(
(
101 MHz, DMSO-d
6
2
6.83 (d, 1H, J = 7.2 Hz, ArH), 4.53 (s, 2H, CH
MHz, DMSO-d ) d: E-isomer: 193.7 (CH CO), 172.0 (COO),
155.4 (CH), 143.7 (PhCNH), 129.9 (PhCH), 128.3 (PhCH), 121.9
(PhCH), 118.4 (PhCCl), 114.7 (PhCH), 91.4 (CH=C), 71.5 (CH );
Z-isomer: 192.8 (CH CO), 173.7 (COO), 155.4 (CH), 141.3
(PhCNH), 130.2 (PhCH), 128.4 (PhCH), 122.1 (PhCH), 119.2
2
); C NMR (101
CH), 89.6 (CH=C), 71.0 (CH
2
), 48.1 (CH
3
3
6
2
+
m/z: 155.1 (M) . Data for 5a: Tan powder, yield 69.7%, mp
1
1
68.3-169.3 °C; IR (KBr) v: 3284, 3076, 2929, 1739, 1670, 1580,
-1 1
479, 1299, 1029, 752, 694 cm ; H NMR (400 MHz, DMSO-d
2
6
)
2
d: 11.04 (s, 1H, ArNHNH), 8.93 (s, 1H, ArNHNH), 7.77 (s, 1H,
CH=C), 7.24 (t, 2H, J = 7.9 Hz, ArH), 6.88 (t, 1H, J = 7.3 Hz,
2
(PhCCl), 114.4 (PhCH), 90.2 (CH=C), 71.0 (CH ); MS m/z (EI):
1
3
+
252.1 (M) ; Anal. Calcd. for C11
ArH), 6.76 (d, 2H, J = 7.9 Hz, ArH), 4.51 (s, 2H, CH
2
); C NMR
CO), 172.2
COO), 155.4 (CH), 147.9 (PhCNH), 129.5 (2C, 2 ´ PhCH),
21.1 (PhCH), 113.8 (2C, 2 ´ PhCH), 91.1 (CH=C), 71.1 (CH );
Z-isomer: 193.9 (CH CO), 172.2 (COO), 155.4 (CH), 147.9
H
9
ClN
2
O
3
(252.65): C, 52.29; H,
(
(
101 MHz, DMSO-d
6
) d: E-isomer: 193.9 (CH
2
3.59; N, 11.09. Found: C, 52.37; H, 3.56; N, 11.16. Data for 5e:
Brilliant yellow powder, yield 26.9%, mp 199.0-121.0 °C; IR
(KBr) v: 3265, 3184, 3019, 2934, 1728, 1664, 1599, 1494, 1296,
1
2
-
1
1
2
6
1033, 827, 781, 695 cm ; H NMR (400 MHz, DMSO-d ) d:
(
PhCNH), 129.8 (2C, 2 ´ PhCH), 121.5 (PhCH), 113.5 (2C, 2 ´
+
); MS m/z (EI): 218.2 (M) ; Anal.
11.05 (s, 1H, ArNHNH), 9.21 (s, 1H, ArNHNH), 7.78 (s, 1H,
CH=C), 7.25 (t, 1H, J = 8.0 Hz, ArH), 6.90 (d, 1H, J = 7.7 Hz,
ArH), 6.77 (s, 1H, ArH), 6.71 (d, 1H, J = 8.2 Hz, ArH), 4.53 (s,
PhCH), 89.7 (CH=C), 71.1 (CH
Calcd. for C11
2
H
10
N
2
O
3
(218.21): C, 60.55; H, 4.62; N, 12.84.
1
3
Found: C, 60.61; H, 4.65; N, 12.80. Data for 5b: Gray powder,
yield 47.4%, mp 167.6-169.5 °C; IR (KBr) v: 3264, 3211, 3039,
2H, CH
(CH CO), 172.1 (COO), 153.9 (CH), 149.4 (PhCNH), 134.0
(PhCCl), 131.1 (PhCH), 120.4 (PhCH), 113.1 (PhCH), 112.3
(PhCH), 91.6 (CH=C), 71.1 (CH ); Z-isomer: 192.9 (CH CO),
2 6
); C NMR (101 MHz, DMSO-d ) d: E-isomer: 192.9
2
-
1 1
2
938, 1726, 1673, 1586, 1487, 1296, 1024, 735 cm ; H NMR
400 MHz, DMSO-d ) d: 11.08 (s, 1H, ArNHNH), 8.97 (s, 1H,
ArNHNH), 7.84 (s, 1H, CH=C), 7.14-7.19 (m, 1H, ArH), 7.09 (t,
H, J = 7.6 Hz, ArH), 6.84-6.92 (m, 2H, ArH), 4.52 (s, 2H, CH );
CO),
72.1 (COO), 155.3 (CH), 149.7 (PhCF), 135.6 (PhCNH), 125.2
(
6
2
2
172.1 (COO), 153.9 (CH), 149.4 (PhCNH), 134.4 (PhCCl), 131.4
1
2
(PhCH), 120.7 (PhCH), 112.7 (PhCH), 112.1 (PhCH), 90.1
+
); MS m/z (EI): 252.2 (M) ; Anal. Calcd. for
1
3
C NMR (101 MHz, DMSO-d
6
) d: E-isomer: 193.7 (CH
2
(CH=C), 71.1 (CH
ClN
2
1
C
11
H
9
2
O
3
(252.65): C, 52.29; H, 3.59; N, 11.09. Found: C,
(
(
PhCH), 121.6 (PhCH), 115.9 (PhCH), 115.7 (PhCH), 91.2
CH=C), 71.0 (CH ); Z-isomer: 193.7 (CH CO), 172.1 (COO),
55.3 (CH), 152.1 (PhCF), 135.5 (PhCNH), 125.2 (PhCH), 121.7
52.15; H, 3.59; N, 11.03. Data for 5f: Yellow powder, yield
49.6%, mp 195.3-196.3 °C; IR (KBr) v: 3243, 3184, 3008, 2935,
2
2
-
1 1
1
1751, 1643, 1572, 1480, 1240, 1031, 818 cm ; H NMR (400
MHz, DMSO-d ) d: 11.06 (s, 1H, ArNHNH), 9.09 (s, 1H,
ArNHNH), 7.77 (s, 1H, CH=C), 7.28 (d, 2H, J = 8.7 Hz, ArH),
(
PhCH), 115.8 (PhCH), 115.6 (PhCH), 90.0 (CH=C), 71.0 (CH
2
);
6
+
MS m/z (EI): 236.2 (M) ; Anal. Calcd. for C11
H
9
FN
2
O
3
(236.20):
1
3
C, 55.93; H, 3.84; N, 11.86. Found: C, 56.01; H, 3.85; N, 11.84.
6.77 (d, 2H, J = 8.7 Hz, 2H, ArH), 4.52 (s, 2H, CH
(101 MHz, DMSO-d ) d: E-isomer: 193.4 (CH
(COO), 154.4 (CH), 146.9 (PhCNH), 129.2 (2C, 2 ´ PhCH),
124.5 (PhCH), 115.1 (2C, 2 ´ PhCH), 91.3 (CH=C), 71.1 (CH );
Z-isomer: 193.1 (CH CO), 173.7 (COO), 154.4 (CH), 144.2
2
); C NMR
Data for 5c: Tan powder, yield 30.5%, mp 167.2-169.2 °C; IR
6
2
CO), 172.1
(
KBr) v: 3285, 3065, 2929, 1740, 1674, 1583, 1498, 1210, 1025,
-
1
1
26 cm ; H NMR (400 MHz, DMSO-d
8
6
) d: 11.05 (s, 1H,
2
ArNHNH), 8.87 (s, 1H, ArNHNH), 7.78 (s, 1H, CH=C), 7.09 (t,
2
498
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© 2015 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2015, 62, 495-500