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4.1.5. N0-(2-Furylmethylidene)-6-nitro-1,3-benzodioxole-
5-carbohydrazine (3a). The derivative (3a) was obtained
as a yellow solid by condensation of (10) with furfural-
dehyde (0.26 g; 88%), mp 226–228 ꢁC. 1H NMR
(200 MHz, DMSO-d6, TMS) d (ppm): 6.30 (s, 10H, H-
2E/Z); 6.54 (dd, 2H, J = 1.8 Hz, H-400Z); 6.64 (dd, 3H,
J = 1.8 Hz, H-400E); 6.72 (d, 2H, J = 3.4 Hz, H-300Z);
6.95 (d, 3H, J = 3.4 Hz, H-300E); 7.15 (s, 2H, H-40Z);
7.30 (s, 3H, H-40E); 7.74 (d, 7H, J = 4.6 Hz, H-500Z,
H-4E/Z); 7.87 (d, 5H, H-500E, H-7Z); 8.10 (s, 3H, H-
7E); 11.87 (s, 2H, H-20Z); 11.90 (s, 3H, H-20E). 13C
NMR (50 MHz, DMSO-d6, TMS) d (ppm): 104.4 (C-
2); 104.7 (C-7); 105.5 (C-4); 108.5 (C-300); 108.9 (C-300);
112.5 (C-400); 112.7 (C-400); 128.6 (C-5); 134.9 (C-40);
138.1 (C-40); 141.2 (C-6); 145.5 (C-500); 145.9 (C-500);
148.8 (C-200); 149.6 (C-200); 152.2 (C-1a); 152.6 (C-3a);
161.9 (C-10); 167.9 (C-10). IR (emax, KBr) e (cmꢀ1):
3197, 3123, 3061, 2918, 2855, 1644, 1623, 1533, 1504,
1486, 1381, 1293, 1281, 1261, 1164, 1126, 1033, 1017,
939, 877, 763.
hyde (0.30 g; 95%), mp 216–218 ꢁC. 1H NMR
(200 MHz, DMSO-d6, TMS) d (ppm): 6.31 (s, 66H,
H-2E/Z); 7.34 (m, 165H, H-200,300,400,500,600E/Z); 7.45
(s, 10H, H-4Z); 7.72 (s, 23H, H-4E); 7.76 (s, 33H,
H-7E/Z); 7.99 (s, 10H, H-40Z); 8.22 (s, 23H, H-40E);
11.94 (s, 10H, H-20Z); 11.97 (s, 23H, H-20E). 13C
NMR (50 MHz, DMSO-d6, TMS) d (ppm): 104.4
(C-2); 104.6 (C-7); 108.6 (C-4); 108.9 (C-4); 127.1
(C-300,500); 127.7 (C-300,500); 128.4 (C-5); 129.2 (C-
200,600); 129.3 (C-200,600); 130.4 (C-400); 130.7 (C-400);
141.6 (C-6); 144.8 (C-40); 148.8 (C-40); 152.3 (C-1a);
152.7 (C-3a); 162.0 (C-10); 168.0 (C-10). IR (emax
,
KBr) e (cmꢀ1): 3222, 3114, 3059, 2916, 2851, 1646,
1607, 1533, 1503, 1485, 1381, 1279, 1161, 1123, 1033,
928, 878, 768, 693.
4.1.9. 6-Nitro-N0-(2-pyridinylmetilidene)-1,3-benzodioxole-
5-carbohydrazine (3e). The derivative (3e) was obtained
as a yellow solid by condensation of (10) with 2-pyridin-
ecarboxaldehyde (0.26 g; 84%), mp 184–185 ꢁC. 1H
NMR (200 MHz, DMSO-d6, TMS) d (ppm): 6.32 (s,
20H, H-2E/Z); 7.37 (m, 10H, H-500,600E/Z); 7.58 (s,
10H, H-4E/Z); 7.74 (m, 10H, H-7E/Z); 7.91 (m, 10H,
H-400E/Z); 8.03 (s, 3H, H-40Z); 8.24 (s, 7H, H-40E);
8.54 (d, 3H, J = 3.6 Hz, H-300Z); 8.62 (d, 7H,
J = 4.2 Hz, H-300E); 12.15 (s, 3H, H-20Z); 12.19 (s, 7H,
H-20E). 13C NMR (50 MHz, DMSO-d6, TMS) d
(ppm): 104.5 (C-2); 104.6 (C-7); 105.5 (C-4); 108.7
(C-300); 108.9 (C-300); 119.5 (C-500); 120.5 (C-500); 124.8
(C-400); 125.1 (C-400); 127.2 (C-5); 137.3 (C-40); 137.4
(C-40); 144.8 (C-6); 150.0 (C-600); 150.1 (C-600); 153.2
(C-1a); 155.5 (C-3a); 155.9 (C-200); 156.2 (C-200); 165.4
(C-10); 171.3 (C-10). IR (emax, KBr) e (cmꢀ1): 3427,
3198, 3122, 3063, 2983, 2925, 2854, 1663, 1609, 1523,
1505, 1485, 1432, 1368, 1336, 1288, 1262, 1163, 1126,
1032, 921, 874, 777, 762, 640, 583.
4.1.6. 6-Nitro-N0-(2-thienylmethylidene)-1,3-benzodioxole-
5-carbohydrazine (3b). The derivative (3b) was obtained
as a yellow solid by condensation of (10) with 2-thio-
phenecarboxaldehyde (0.29 g; 90%), mp 240–242 ꢁC.
1H NMR (200 MHz, DMSO-d6, TMS) d (ppm): 6.30
(s, 10H, H-2E/Z); 7.03 (dd, 2H, J = 3.6 Hz, H-400Z);
7.13 (m, 5H, H-400E, H-300Z); 7.31 (m, 5H, H-300E, H-
40Z); 7.50 (m, 5H, H-40E, H-500Z); 7.71 (m, 8H, H-4E/
Z, H-500E); 8.14 (s, 2H, H-7Z); 8.42 (s, 3H, H-7E);
11.88 (s, 2H, H-20Z); 11.92 (s, 3H, H-20E). 13C NMR
(50 MHz, DMSO-d6, TMS) d (ppm): 104.4 (C-7);
104.5 (C-2); 105.4 (C-4); 108.6 (C-500); 108.9 (C-500);
128.1 (C-5); 128.2 (C-400); 128.3 (C-400); 129.1 (C-300);
129.7 (C-300); 130.9 (C-40); 131.8 (C-40); 141.5 (C-6);
143.4 (C-500); 148.7 (C-1a); 149.1 (C-3a); 152.2 (C-200);
152.6 (C-200); 161.7 (C-10); 167.8 (C-10). IR (emax, KBr)
e (cmꢀ1): 3191, 3073, 3060, 3032, 2992, 2915, 2844,
1639, 1608, 1591,1560, 1531, 1503, 1485, 1380, 1290,
1264, 1222, 1162, 1125, 1033, 1015, 928, 878, 713.
4.1.10. 6-Nitro-N0-(4-pyridinylmetilidene)-1,3-benzodiox-
ole-5-carbohydrazine (3f). The derivative (3f) was
obtained as a yellow solid by condensation of (10)
with 4-pyridinecarboxaldehyde (0.28 g; 89%), mp 202–
203 ꢁC. 1H NMR (200 MHz, DMSO-d6, TMS) d
(ppm): 6.31 (s, 20H, H-2E/Z); 7.32 (d, 6H, J = 4.9 Hz,
H-200,600Z); 7.52 (s, 3H, H-4Z); 7.71 (d, 14H,
J = 5.8 Hz, H-200,600E); 7.77 (s, 7H, H-4E); 7.99 (s, 3H,
H-40Z); 8.23 (s, 7H, H-40E); 8.56 (d, 6H, J = 4.9 Hz,
H-300,500Z); 8.68 (d, 14H, J = 5.8 Hz, H-300,500E); 12.27
(s, 3H, H-20Z); 12.30 (s, 7H, H-20E). 13C NMR
(50 MHz, DMSO-d6, TMS) d (ppm): 104.7 (C-2,7);
108.6 (C-4); 121.2 (C-300,500); 121.7 (C-300,500); 124.9 (C-
5); 141.7 (C-6); 142.2 (C-40); 144.7 (C-400); 145.0 (C-400);
145.8 (C-40); 150.2 (C-200,600); 150.3 (C-200,600); 152.5
(C-1a); 153.4 (C-3a); 167.0 (C-10); 171.5 (C-10). IR
(emax, KBr) e (cmꢀ1): 3450, 3198, 3119, 3050, 2996,
2920, 2857, 1670, 1581, 1530, 1508, 1489, 1421, 1370,
1337, 1298, 1268, 1162, 1125, 1030, 923, 881, 818, 744,
693, 537.
4.1.7. N0-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-6-nitro-
1,3-benzodioxole-5-carbohydrazine (3c). The derivative
(3c) was obtained as a yellow solid by condensation
of (10) with 3,5-di-tert-butyl-4-hydroxybenzaldehyde
(0.36 g; 82%), mp 280–282 ꢁC. 1H NMR (200 MHz,
DMSO-d6, TMS) d (ppm): 1.32 (s, 18H, –CH3Z); 1.40
(s, 36H, –CH3E); 6.29 (m, 6H, H-2E/Z); 7.15 (m, 6H,
H-200,600E/Z); 7.27 (s, 1H, H-4Z); 7.47 (s, 2H, H-4E);
7.67 (m, 1H, H-40Z); 7.73 (s, 2H, H-40E); 7.83 (s, 3H,
H-7E/Z); 11.69 (s, 1H, H-20Z); 11.76 (s, 2H, H-20E).
13C NMR (50 MHz, DMSO-d6, TMS) d (ppm): 30.5
(–CH3); 34.9 (C-Me3); 104.0 (C-7); 104.2 (C-2); 108.7
(C-4); 124.0 (C-5); 124.4 (C-200,600); 128.6 (C-100); 139.5
(C-300,500); 142.0 (C-6); 145.0 (C-40); 148.6 (C-400); 152.5
(C-1a); 156.3 (C-3a); 167.7 (C-10). IR (emax, KBr) e
(cmꢀ1): 3593, 3172, 3065, 2962, 2872, 1662, 1612,
1527, 1509, 1487, 1433, 1401, 1372, 1342, 1259, 1236,
1212, 1139, 1117, 1032, 927, 875, 766.
4.1.11. 6-Nitro-N0-(1H-pyrrol-2-ylmethylidene)-1,3-ben-
zodioxole-5-carbohydrazine (3g). The derivative (3g)
was obtained as a yellow solid by condensation of (10)
with 1H-pyrrol-2-ylcarboxaldehyde (0.27 g; 89%), mp
4.1.8. N0-Benzylidene-6-nitro-1,3-benzodioxole-5-carbo-
hydrazine (3d). The derivative (3d) was obtained as a
yellow solid by condensation of (10) with benzalde-
1
202–203 ꢁC. H NMR (200 MHz, DMSO-d6, TMS) d