2
686
GUL et al.
1
7
.8 d (2H, J = 7.9 Hz, Ar-H), 10.11 s (1H, N–H), 11.46
443.6, 411.1. H NMR spectrum, δ, ppm: 4.13 s (5H,
C H ), 4.33 t (2H, J = 1.9 Hz, C H ), 4.86 t (2H, J =
1
3
s (1H, N–H). C NMR spectrum, δ, ppm: 66.2 (2C),
5
5
5
4
6
1
1
7.1 (2C), 68.3 (5C), 82.95, 120.5, 121.1 (2C), 121.5,
22.5 (2C), 124.8, 129.2 (2C), 129.6 (2C), 130.2 (2C),
1.9 Hz, C H ), 7.29 d (2H, J = 8.1 Hz, Ar-H), 7.43 d
5 4
(2H, J = 8.1 Hz, Ar-H), 7.61 s (2H, Ar-H), 7.68–7.9 m
(5H, Ar-H), 10.51 s (1H, N–H), 11.55 s (1H, N–H).
31 (2C), 136.4, 139.7, 140.8, 159.5 (CN ), 178.8
3
1
3
(C=O). Found, %: C 73.1; H 5.75; N 7.8. C H N FeO.
C NMR spectrum, δ, ppm: 66.9 (2C), 67.6 (2C), 68.5
(5C), 84.1, 121.9 (2C), 125.1, 127.5, 128.9, 129.2
2C), 129.8 (2C), 130.8 (2C), 133.1, 132.8, 134.7(2C),
38.6, 139.8, 141.2, 160.7 (CN ), 179.1 (C=O). Found,
33
31
3
Calculated, %: C 73.2; H 5.77; N 7.76.
(
1
N-(4-Ferrocenylphenyl)-N'-(4-chlorophenyl)-N''-
benzoylguanidine (2). Yield 74%, mp 158–159°C.
FT-IR spectrum, ν, cm : 3335.3, 3166.7, 3088.1,
3
–
1
%: C 59.76; H 3.64; N 9.3 %. C H N Cl FeO.
30 22 3 3
Calculated, %: C 59.78; H 3.68; N 9.27.
2
1
7
975.6, 1667.2, 1576.7, 1559.6, 1524.6, 1450.4, 1361.3,
372.5, 1309.5, 1267.6, 1145.4, 1075.6, 1012.3, 837.9,
25.8, 667.4, 625.5, 567.4, 518.3, 478.3, 445.4, 409.7.
N-(4-Ferrocenylphenyl)-N'-(2,4,6-trichlorophenyl)-
N''-benzoylguanidine (5). Yield 74%, mp 160.6–
1
–1
H NMR spectrum, δ, ppm: 4.18 s (5H, C H ), 4.32 t
161.4°C. FT-IR spectrum, ν, cm : 3356.6, 3283.2,
5
5
(
7
2H, J = 1.9 Hz, C H ), 4.81 t (2H, J = 1.9 Hz, C H ),
.22 d (2H, J = 8.1 Hz, Ar-H), 7.3 d (2H, J = 7.9 Hz,
3138.8, 3051.2 1663.3, 1575.1, 1556.5, 1508.1, 1442.3,
1440.5, 1365.2, 1253.6, 1235.1, 1181.5, 1101.8, 1070.1,
1022.4, 956.4, 845.3, 802.1, 604.6, 577.2, 471.1, 443.6,
5
4
5
4
Ar-H), 7.4 d (2H, 7.9 Hz, Ar-H), 7.54 d (2H, 8.1 Hz,
Ar-H), 7.6–7.9 m (5H, Ar-H), 10.45 s (1H, N–H),
1
409.3. H NMR spectrum, δ, ppm: 4.11 s (5H, C H ),
5
5
1
3
1
1.46 s (1H, N–H). C NMR spectrum, δ, ppm: 66.8
2C), 67.3 (2C), 68.7 (5C), 83.44, 120.8 (2C), 122.9,
24.4, 125.1, 129.2 (2C), 129.6 (2C), 130.2 (2C), 131
2C), 133.7 (2C), 135.5, 139.7, 141.4, 160.2 (CN3),
78.6 (C=O). Found, %: C 67.47; H 4.51; N 7.89.
C H N ClFeO. Calculated, %: C 67.50; H 4.53; N
4.32 t (2H, J = 1.9 Hz, C H ), 4.91 t (2H, J = 1.9 Hz,
5 4
(
1
(
1
C H ), 7.28 d (2H, J = 8.1 Hz, Ar-H), 7.41 d (2H, J =
5 4
8.1 Hz, Ar-H), 7.55 s (2H, Ar-H), 7.65 t (1H, J =
7.9 Hz, Ar-H), 7.71 t (2H, J = 7.9 Hz, Ar-H), 7.96 d
(2H, J = 7.9 Hz, Ar-H), 10.51 s (1H, N–H), 11.6 s (1H,
1
3
N–H). C NMR spectrum, δ, ppm: 66.8 (2C), 67.5
3
0
24
3
7
.87.
N-(4-Ferrocenylphenyl)-N'-(2,3,4-trichlorophenyl)-
N''-benzoylguanidine (3). Yield 76%, mp 159–160°C.
(2C), 68.5 (5C), 84.2, 121.7 (2C), 126.1, 127.5 (2C),
1
1
28.6, 129.4 (2C), 129.9 (2C), 130.6 (2C), 133.8,
34.7, 136.6 (2C), 139.3, 141, 161 (CN ), 179 (C=O).
3
–1
Found, %: C 59.76; H 3.64; N 9.28%. C H
30 22
FT-IR spectrum, ν, cm : 3341.2, 3287.3, 3130.6, 3028.1,
N Cl FeO. Calculated, %: C 59.78; H 3.68; N 9.27.
3
3
1
1
8
675.5, 1563.1, 1552.5, 1452.6, 1432.7, 1378.4, 1313.7,
263.6, 1259.1, 1182.7, 1107.8, 1065.2, 1002.1, 957.4,
N-(4-Ferrocenylphenyl)-N'-(2,3,5,6-tetrachloro-
phenyl)-N''-benzoylguanidine (6). Yield 78%, mp
1
72.8, 804.1, 537.2, 476.1, 441.6, 423.5. H NMR
–1
spectrum, δ, ppm: 4.18 s (5H, C H ), 4.33 t (2H, J =
1
158.5–159.8°C. FT-IR spectrum, ν, cm : 3466.6,
3281.2, 3108.8, 1675.3, 1558.5, 1508.7, 1457.3, 1406.7,
1381.4, 1260.6, 1233.1, 1181.5, 1103.1, 1072.2, 1011.1,
965.4,875.4, 800.1, 601.6, 540.5, 518.8, 474.1, 443.6.
5
5
.9 Hz, C H ), 4.84 t (2H, J = 1.9 Hz, C H ), 7.27 d
5 4 5 4
(
7
2H, J = 8.1 Hz, Ar-H), 7.43 d (1H, J = 7.9 Hz, Ar-H),
.53 d (2H, J = 8.1 Hz, Ar-H), 7.6 d (1H, J = 7.9 Hz,
Ar-H), 7.65 t (1H, J = 7.9 Hz, Ar-H), 7.75 t (2H, J =
.9 Hz, Ar-H), 8.1 d (2H, J = 7.9 Hz, Ar-H), 10.61 s
1
H NMR spectrum, δ, ppm: 4.12 s (5H, C H ), 4.33 t
5
5
7
(2H, J = 1.9 Hz, C H ), 4.9 t (2H, J = 1.9 Hz, C H ),
5 4 5 4
1
3
(1H, N–H), 11.53 s (1H, N–H). C NMR spectrum, δ,
ppm: 66.9 (2C), 67.5 (2C), 68.7 (5C), 84.1, 122.3 (2C),
7.29 d (2H, J = 8.1 Hz, Ar-H), 7.39 d (2H, J = 8.1 Hz,
Ar-H), 7.45 s (1H, Ar-H), 7.55 t (1H, J = 7.9 Hz,
Ar-H), 7.75 t (2H, J = 7.6 Hz, Ar-H), 7.91 d (2H, J =
7.6 Hz, Ar-H), 10.51 s (1H, N–H), 11.58 s (1H, N–H).
1
1
1
25.3, 127.1, 128.6, 129.3, 129.8 (2C), 130.6 (2C),
31.8 (2C), 132.3, 134.7, 136.6, 139.9, 140.5, 141.1,
1
3
60.9 (CN ), 179.4 (C=O). Found, %: C 59.75; H 3.64;
C NMR spectrum, δ, ppm: 66.9 (2C), 67.6 (2C), 68.5
3
N 9.2. C H N Cl FeO. Calculated, %: C 59.78; H
(5C), 84.2, 122.3 (2C), 126.1, 127.5 (2C), 128.6, 129.1
(2C), 129.9 (2C), 130.6 (2C), 133.1 (2C), 135.7, 139.8,
30
22
3
3
3
.68; N 9.27.
N-(4-Ferrocenylphenyl)-N'-(3,4,5-trichlorophenyl)-
N''-benzoylguanidine (4). Yield 78%, mp 159.1–
1
5
40.5, 141.1, 160.9 (CN ), 179 (C=O). Found, %: C
3
6.53; H 3.30; N 8.77C. C H N Cl FeO. Calculated,
3
0
21
3
4
–1
%: C 56.55; H 3.32; N 8.76.
160.2°C. FT-IR spectrum, ν, cm : 3366.6, 3282.2, 3008.8,
1683.3, 1575.1, 1558.5, 1508.4, 1456.3, 1442.7, 1384.4,
1310.9, 1263.6, 1233.1, 1182.5, 1103.8, 1070.2, 1012.1,
960.4, 872.4, 800.1, 609.6, 584.2, 543.5, 520.8, 476.1,
Biological evaluation. DPPH free radical scavenging
activity. The earlier reported protocol was followed
with slight modifications [14]. The samples were
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 11 2017