SAVANI ET AL.
13 of 15
[
6
C H FeN O ]: C, 68.37; H, 6.13; N, 8.25. Found: C,
(400 MHz, CDCl ) δppm 170.1, 151.1, 142.1, 110.5, 107.3,
81.4, 68.6, 58.0, 54.9, 36.1, 30.9. IR (KBr, cm ): 3340 (N-
29
31
3
2
3
1
−1
8.51; H, 6.20; N, 8.38. H NMR (400 MHz, CDCl ) δ
3
ppm: 7.62(s, 2H, -NHCO); 6.94–7.37(m, 10H, Ph);
H), 2,920 (C-H), 2850 (C-H), 1674 (C=O), 1651 (C=O),
1508, 1423, 1356, 1284, 1203, 1145, 1107, 1018, 756, 740,
474.
4
.07–4.38 (m, 9H, Fc); 4.45 (s, 4H, -CH CO); 3.51(s, 4H,
2
13
-
CH Ph); 3.17 (2H, s, –CH Fc). C NMR (400 MHz,
2
2
CDCl ) δ ppm: 170.1, 138.1, 128.7, 127.7, 127.5, 69.8, 68.6,
2-(ferrocenylmethylamino)-N-paramethylaceta-
mide (4a). Yellow oily liquid; MW 376. Yield: ꢁ229 mg,
61%. Anal. Calcd for [C H FeN O]: C, 67.03; H, 6.43; N,
3
−
1
5
8.2, 55.1, 43.2, 30.9. IR (KBr, cm ): 3448 (N-H), 3313(N-
H), 2962 (C-H), 2920 (C-H), 1670 (C=O), 1639 (C=O),
539, 1504, 1450, 1427, 1261, 1103, 1022, 802, 698, 482.
-(ferrocenylmethylamino)-N-cyclohexylaceta-
2
1
24
2
1
1
7.44. Found: C, 67.12; H, 6.49; N, 7.53 H NMR
2
(400 MHz, CDCl ) δ ppm: 7.50(s, 1H, -NHCO); 7.13–7.49
3
mide (2a). Yellow oily liquid; MW 354. Yield: ꢁ212 mg,
(m, 4H, Ph); 4.42 (d, J = 6 Hz, 2H, -CH CO); 4.08–4.16
2
6
7
0%. Anal. Calcd for [C H FeN O]: C, 64.42; H, 7.40; N,
.91. Found: C, 64.50; H, 7.46; N, 7.98. H NMR
(m, 9H, Fc); 3.47 (s, 2H, -CH Ph); 3.33(s, 2H, -CH Fc);
19
26
2
2
2
1
13
2.34(s, 3H, CH3). C NMR (400 MHz, CDCl ) δ ppm:
3
(
(
400 MHz, CDCl ) δ ppm: 6.51 (s, 1H, -NHCO); 4.14–4.22
170.5, 137.1, 135.1, 129.3, 127.7, 68.5, 51.0, 48.9, 42.8,
3
−1
m, 9H, Fc); 3.62 (m, 1H, Cy); 3.40 (s, 2H, –CH Fc); 3.20
21.1. IR (KBr, cm ): 3317 (N-H), 3086 (C-H), 3008 (C-
H), 2835 (C-H), 2823 (C-H), 1658 (C=O), 1519, 1427,
1357, 1257, 1103, 1026, 810, 478.
2
(
1
s, 2H, –CH CO); 2.08 (s, 1H, NH(-CH Fc)) 1.19–1.90 (m,
2
2
13
0H, Cy). C NMR (400 MHz, CDCl ) δ, ppm 168.1, 81.0,
8.6, 33.0, 32.8, 30.9, 25.4, 24.7, 21.6. IR (KBr, cm ): 471
3
−1
0
6
2,2 -(ferrocenylmethylazanediyl)bis(N-para-
(
1
N-H), 3163(C-H), 2800 (C-H), 1666(C=O), 1550, 1404,
methylacetamide) (4b). Yellow solid; MW 537. Yield:
ꢀ
234, 1103, 1126, 910, 810, 648, 439.
ꢁ483 mg, 90%. Melting point: 123 C. Anal. Calcd for
0
2
, 2 -(ferrocenylmethylazanediyl)bis(N-cyclohex-
[C H FeN O ]: C, 69.27; H, 6.56; N, 7.82. Found: C,
3
1
35
3 2
1
ylacetamide) (2b). Yellow solid; MW 493. Yield:
69.33; H, 6.61; N, 7.87. H NMR (400 MHz, CDCl ) δ
3
ꢀ
ꢁ
419 mg, 85%. Melting point: 153 C. Anal. Calcd for
ppm: 7.141(m, 5H, Ph); 6.9(s, 1H, -NHCO); 3.98–4.35 (m,
[
C H FeN O ]: C, 65.72; H, 7.97; N, 8.52. Found: C,
27 39 3 2
9H, Fc); 4.35 (s, 2H, -CH CO); 3.56 (s, 2H, -CH Ph); 3.19
2
2
1
13
6
5.79; H, 8.06; N, 8.65. H NMR (400 MHz, CDCl ) δ
(s, 2H, -CH Fc); 2.36 (s, 3H, CH ). C NMR (400 MHz,
2 3
3
ppm: 6.51 (s, 2H, NHCO); 4.12–4.17(m, 9H, Fc); 3.78 (m,
CDCl ) δ ppm: 166.7, 137.3, 134.3, 129.4, 127.8, 44.2, 21.1.
3
−
1
2
H, Cy); 3.54 (s, 2H,–CH Fc); 3.12 (s, 4H,–CH CO);
IR (KBr, cm ): 3360 (N-H), 3321(C-H), 2920 (C-H), 2854
(C-H), 1670 (C=O), 1639 (C=O), 1535, 1431, 1257, 1107,
1026, 840, 802, 752, 470.
2
2
1
3
1
.12–1.91(m, 20H, Cy). C NMR (400 MHz, CDCl ) δ,
ppm 169.3, 81.8, 69.8, 68.6, 58.2, 55.1, 47.8, 33.08, 30.9,
3
−
1
2
(
1
5.4, 24.7. IR (KBr, cm ): 3321(N-H), 2,931 (C-H), 2846
C-H), 1681(C=O), 1643(C=O), 1535, 1450, 1315, 1253,
103, 1026, 817,759, 493, 478.
-(ferrocenylmethylamino)-N-furfurylacetamide
3a). Yellow oily liquid; MW 352. Yield: ꢁ222 mg, 63%.
Anal. Calcd for [C H FeN O ]: C, 61.38; H, 5.72; N,
2-(ferrocenylmethylamino)-N-parametho-
xybenzylacetamide (5a). Yellow oily liquid; MW 392.
Yield: ꢁ243 mg, 62%. Anal. Calcd for [C H FeN O ]: C,
21
24
2 2
2
64.30; H, 6.17; N, 7.14. Found: C, 64.35; H, 6.24; N, 7.20.
1
(
H NMR (400 MHz, CDCl ) δ ppm: 7.50(s, 1H, -NHCO);
3
7.2(d, J = 8.8 Hz, 2H, Bz); 6.8(d, J = 8.7 Hz, 2H, Ph);
18
20
2 2
1
7
.95. Found: C, 61.47; H, 5.90; N, 8.08. H NMR
6.84–4.30 (d, J = 6.0 Hz, 2H, -CH CO); 4.01–4.32 (m, 9H,
2
(
400 MHz, CDCl ) δ ppm: 7.64 (s, 1H, NHCO); 7.28 (d,
Fc); 3.96 (s, 3H, -OCH ); 3.74 (s, 2H, -CH Ph); 3.23 (s,
3
3
2
13
J = 0.8 Hz, 1H, furyl); 6.34 (t, J = 2 Hz, 1H, furyl); 6.23
d, J = 2.8 Hz, 1H, furyl); 4.14–4.19 (m, 9H, Fc); 4.44 (s,
H, -CH furyl); 3.59 (2H, s, –CH Fc); 3.42(s, 2H, –
2H,–CH Fc). C NMR (400 MHz, CDCl ) δ ppm: 170.7,
158.8, 130.5, 129.1, 114.0, 84.5, 81.6, 68.5, 55.3, 51.2, 48.8,
42.4. IR (KBr, cm ): 3308(N-H), 3081(C-H), 2931(C-H),
2834(C-H), 1655(C=O), 1513, 1460, 1301, 1247, 1176,
1105, 1133, 1001, 818, 484.
2
3
(
−1
2
2
2
1
3
CH CO) C NMR (400 MHz, CDCl ) δppm: 170.0, 151.1,
2
3
1
42.2, 110.4, 107.4, 83.3, 68.5, 50.6, 48.4, 36.1. IR (KBr,
−
1
0
cm ): 3201 (N-H), 2885 (C-H), 2816 (C-H), 1681(C=O),
2,2 -(ferrocenylmethylazanediyl) bis(N-parame-
1
527, 1338, 1265, 1018, 887, 810, 748, 655, 486.
thoxybenzylacetamide) (5b). Yellow solid; MW 569.
0
ꢀ
2
, 2 -(ferrocenylmethylazanediyl)bis(N-furfuryla-
Yield: ꢁ523 mg, 92%. Melting point: 170 C. Anal. Calcd
cetamide) (3b). Yellow solid; MW 489. Yield: ꢁ430 mg,
for [C H FeN O ]: C, 65.38; H, 6.20; N, 7.38. Found: C,
3
1
35
3 4
ꢀ
1
8
8%. Melting point: 132 C. Anal. Calcd for
65.47; H, 6.29; N, 7.42. H NMR (400 MHz, CDCl ) δ
3
[
6
C H FeN O ]: C, 61.36; H, 5.56; N, 8.59. Found: C,
ppm: 7.59 (s, 2H, -NHCO); 7.2(d, J = 8.8 Hz, 2H, Ph); 7.1
(d, J = 8.7 Hz, 2H, Ph); 6.84–7.27 (m, 4H, Ph); 4.35 (d,
4H, -CH CO); 4.05–4.30 (m, 9H, Fc); 3.97 (s, 6H, -OCH );
25
27
3 4
1
1.44; H, 5.61; N, 8.63. H NMR (400 MHz, CDCl ) δ
3
ppm: 7.37 (d, J = 0.8 Hz, 2H, furyl); 6.89 (s, 2H, NHCO);
.34 (t, J = 1.2 Hz, 2H, furyl); 6.23(s, J = 2.8 Hz, 2H,
furyl); 4.42 (s, 4H, -CH furyl); 4.05–4.12 (m, 9H, Fc); 3.50
2
3
13
6
3.79 (s, 4H, -CH Ph); 3.15 (s, 2H,–CH Fc). C NMR
2
2
(400 MHz, CDCl ) δ ppm: 170.0, 138.1, 128.7, 127.7,
2
3
13
−1
(2H, s, –CH Fc); 3.17(s, 4H, –CH CO).
C NMR
127.5, 69.8, 68.6, 58.2, 55.1, 43.2, 30.9. IR (KBr, cm ):
2
2