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65.35, 110.79, 115.69, 116.87, 119.93, 129.39, 129.80, 133.22, 140.99,
4.7.21. N-(4-((2-(1-(4-(1H-Pyrrol-1-yl)phenyl)ethylidene)
145.39, 150.65, 150.77, 169.81; MS (ESI): m/z ¼ found 349.21 [Mþ];
calcd. 349.14. Anal. Calcd. for C20H19N3O3: C, 68.75; H, 5.48; N,
12.03. Found: C, 69.03; H, 5.46; N, 12.08.
hydrazinyl)sulfonyl)phenyl)acetamide (4u)
(Yield 70%). mp 256e258 ꢃC (D); FTIR (KBr): 3369 (NH), 3111,
2924, 2855 (AreH), 1681 (C]O), 1594 (C]N), 1329 (SOa2sym), 1156
(SOs2ym) cmꢀ1 1H NMR (400 MHz, DMSO-d6)
; d ppm: 2.13 (s, 3H,
4.7.17. N0-(1-(4-(1H-Pyrrol-1-yl)phenyl)ethylidene)-2-(2,4,6-
trichlorophenoxy)acetohydrazide (4q)
COCH3), 2.21 (s, 3H, CH3), 6.28 (s, 2H, pyrroleeC3, C4eH), 7.18 (s, 2H,
pyrroleeC2, C5eH), 7.43 (d, 2H, J ¼ 8.7, phenyleC3, C5eH), 7.70 (d,
2H, J ¼ 8.7, sulfonamidephenyleC3, C5eH), 7.79 (d, 2H, J ¼ 8.6,
phenyleC2, C6eH), 7.87 (d, 2H, J ¼ 8.8, sulfonamidephenyleC2, C6e
H), 10.14 (s, 1H, CONH), 10.31 (s, 1H, NH); 13C NMR (100 MHz,
(Yield 63%). mp 256e258 ꢃC; FTIR (KBr): 3212 (NH), 3109, 2923
(AreH), 1689 (C]O), 1606 (C]N), 1257 (CeOeC), 715 (CeCl) cmꢀ1
;
1H NMR (400 MHz, DMSO-d6)
d ppm: 2.32 (s, 3H, CH3), 5.21 (s, 2H,
OCH2), 6.31 (t, 2H, J ¼ 2.1, pyrroleeC3, C4eH), 7.25 (t, 2H, J ¼ 2.0,
pyrroleeC2, C5eH), 7.45e7.49 (m, 2H, phenoxyeC3, C5eH), 7.51 (d,
2H, J ¼ 8.6, phenyleC3, C5eH), 7.81 (d, 2H, J ¼ 8.6, phenyleC2, C6e
DMSO-d6) d ppm: 13.97, 24.01, 110.62, 118.24, 118.53, 118.75, 127.14,
128.52, 132.51, 134.16, 140.40, 143.15, 151.87, 168.75; MS (ESI): m/
z ¼ found 395.11 [Mþ ꢀ 1], 396.11 [Mþ]; calcd. 396.13. Anal. Calcd.
for C20H20N4O3S: C, 60.59; H, 5.08; N, 14.13. Found: C, 60.83; H,
5.06; N, 14.07.
H), 10.87 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6)
d ppm: 13.36,
65.80, 110.78, 120.00, 129.31, 129.43, 129.87, 129.91, 133.49, 141.88,
145.88, 152.33, 169.89; MS (ESI): m/z ¼ found 435.27 [Mþ], 437.22
[Mþþ2]; calcd. 435.03. Anal. Calcd. for C20H16Cl3N3O2: C, 55.00; H,
3.69; N, 9.62. Found: C, 54.78; H, 3.70; N, 9.66.
4.7.22. N0-(1-(4-(1H-Pyrrol-1-yl)phenyl)ethylidene)-4-
aminobenzenesulfonohydrazide (4v)
(Yield 62%). mp 225e227 ꢃC; FTIR (KBr): 3274, 3085 (NH), 2957
4.7.18. N0-(1-(4-(1H-Pyrrol-1-yl)phenyl)ethylidene)-2-
(naphthalen-1-yloxy)acetohydrazide (4r)
(AreH), 1513 (C]N), 1316 (SOa2sym), 1129 (SOs2ym) cmꢀ1 1H NMR
;
(400 MHz, DMSO-d6) d ppm: 2.20 (s, 3H, CH3), 6.29 (s, 2H, pyrroleeC3,
(Yield 71%). mp 210e212 ꢃC; FTIR (KBr): 3191 (NH), 3093, 2922
C4eH), 6.37 (s, 1H, NH2), 7.18 (s, 2H, pyrroleeC2, C5eH), 7.02 (d, 2H,
J ¼ 7.9, sulfonamidephenyleC3, C5eH), 7.47 (d, 2H, J ¼ 8.2, phenyleC3,
C5eH), 7.71 (d, 2H, J ¼ 8.3, sulfonamidephenyleC2, C6eH), 7.84 (d, 2H,
J ¼ 8.3, phenyleC2, C6eH), 10.35 (s, 1H, NH); 13C NMR (100 MHz,
(AreH), 1706 (C]O), 1612 (C]N), 1326 (CeOeC) cmꢀ1 1H NMR
;
(400 MHz, DMSO-d6)
d ppm: 2.30 (s, 3H, CH3), 5.36 (s, 2H, OCH2),
6.26 (t, 2H, J ¼ 2.1, pyrroleeC3, C4eH), 6.84 (d, 1H, J ¼ 7.5, naph-
thoxyeC2eH), 7.28 (t, 2H, J ¼ 2.0, pyrroleeC2, C5eH), 7.33e7.37 (m,
1H, naphthoxyeC3eH), 7.42e7.53 (m, 5H, phenyleC3, C5eH and
naphthoxyeC4, C6, C7eH), 7.80e7.88 (m, 3H, naphthoxyeC5eH and
ph-C2, C6eH), 8.30 (t, 1H, J ¼ 2.3, naphthoxyeC8eH), 10.88 (s, 1H,
DMSO-d6) d ppm: 13.83,110.73,112.29,119.20,127.09,128.49,130.03,
134.08, 136.00, 142.60, 151.62, 168.22; MS (ESI): m/z ¼ found 354.41
[Mþ]; calcd. 354.12. Anal. Calcd. for C18H18N4O2S: C, 61.00; H, 5.12; N,
15.81. Found: C, 61.24; H, 5.10; N, 15.87.
NH); 13C NMR (100 MHz, DMSO-d6)
d ppm: 13.38, 65.53, 110.65,
118.62, 118.83, 120.04, 121.80, 124.97, 125.76, 126.22, 127.17, 127.34,
134.01, 134.68, 140.30, 147.54, 153.60, 169.48; MS (ESI): m/z ¼ found
383.05 [Mþ]; calcd. 383.16. Anal. Calcd. for C24H21N3O2: C, 75.18; H,
5.52; N, 10.96. Found: C, 74.88; H, 5.54; N, 10.92.
4.7.23. 1-(4-(1-(2-Phenylhydrazono)ethyl)phenyl)-1H-pyrrole
(4w)
(Yield 69%). mp 195e197 ꢃC; FTIR (KBr): 3350 (NH), 3138, 2923,
2856 (AreH), 1600 (C]N) cmꢀ1 1H NMR (400 MHz, DMSO-d6)
;
d
ppm: 2.28 (s, 3H, CH3), 6.27 (t, 2H, J ¼ 2.1, pyrroleeC3, C4eH), 6.77
4.7.19. N0-(1-(4-(1H-Pyrrol-1-yl)phenyl)ethylidene)-2-
(naphthalen-2-yloxy)acetohydrazide (4s)
(m, 1H, hydrazonophenyleC4eH), 7.17e7.24 (m, 4H, hydrazono-
phenyleC2, C3, C5, C6eH), 7.26 (t, 2H, J ¼ 2.1, pyrroleeC2, C5eH), 7.50
(dd, 2H, J ¼ 2.0, 1.9, phenyleC3, C5eH), 7.84e7.87 (m, 2H, phenyle
(Yield 68%). mp 208e210 ꢃC; FTIR (KBr): 3363 (NH), 3138, 2924,
2857 (AreH), 1690 (C]O), 1607 (C]N), 1328 (CeOeC) cmꢀ1
;
1H
C2, C6eH), 9.15 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6)
d ppm:
NMR (400 MHz, DMSO-d6)
d
ppm: 2.30 (s, 3H, CH3), 5.24 (s, 2H,
17.00, 110.56, 112.99, 119.24, 126.17, 128.80, 129.77, 135.09, 142.80,
143.11, 169.77; MS (ESI): m/z ¼ found 275.37 [Mþ]; calcd. 275.14.
Anal. Calcd. for C18H17N3: C, 78.52; H, 6.22; N, 15.26. Found: C,
78.21; H, 6.25; N, 15.32.
OCH2), 6.25 (t, 2H, J ¼ 2.0, pyrroleeC3, C4eH), 7.13 (s, 1H, naph-
thoxyeC3eH), 7.18 (t, 2H, J ¼ 2.1, pyrroleeC2, C5eH), 7.21e7.29 (m,
2H, naphthoxyeC1, C6eH), 7.37 (s, 1H, naphthoxyeC7eH), 7.46 (d,
2H, J ¼ 8.6, phenyleC3, C5eH), 7.68e7.74 (m, 3H, naphthoxyeC4, C5,
C8eH), 7.84 (d, 2H, J ¼ 8.7, phenyleC2, C6eH), 10.79 (s, 1H, NH); 13
C
4.7.24. 1-(4-(1-(2-(2,4-Dinitrophenyl)hydrazono)ethyl)phenyl)-
1H-pyrrole (4x)
NMR (100 MHz, DMSO-d6)
d ppm: 13.40, 65.39, 105.90, 110.63,
118.56, 118.78, 124.01, 126.63, 126.79, 127.31, 129.33, 129.49, 129.79,
133.73, 141.78, 145.67, 155.63, 169.70; MS (ESI): m/z ¼ found 384.17
[Mþ þ 1], 385.17 [Mþ þ 2]; calcd. 383.16. Anal. Calcd. for C24H21N3O2:
C, 75.18; H, 5.52; N, 10.96. Found: C, 75.48; H, 5.50; N, 10.92.
(Yield 70%). mp 246e248 ꢃC; FTIR (KBr): 3306 (NH), 3102, 2922,
2854 (AreH), 1614 (C]N), 1509 (NO2asym), 1259 (NO2sym) cmꢀ1; 1H
NMR (400 MHz, DMSO-d6)
d ppm: 2.51 (s, 3H, CH3), 6.32 (t, 2H,
J ¼ 2.0, pyrroleeC3, C4eH), 7.30 (t, 2H, J ¼ 2.0, pyrroleeC2, C5eH),
7.59 (d, 2H, J ¼ 8.7, phenyleC3, C5eH), 8.02 (d, 2H, J ¼ 8.7, phenyle
C2, C6eH), 8.17 (d, 1H, J ¼ 9.6, dinitrophenyleC6eH), 8.43 (dd, 1H,
J ¼ 2.6, 2.5, dinitrophenyleC5eH), 9.03 (d, 1H, J ¼ 2.6, dini-
trophenyleC3eH), 11.29 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6)
4.7.20. N0-(1-(4-(1H-Pyrrol-1-yl)phenyl)ethylidene)-4-
methylbenzenesulfonohydrazide (4t)
(Yield 70%). mp 210e212 ꢃC; FTIR (KBr): 3201 (NH), 3066, 3041,
2923 (AreH), 1606 (C]N), 1336 (SOa2sym), 1168 (SO2sym) cmꢀ1
;
1H
d ppm: 17.00, 110.83, 116.12, 118.64, 122.73, 127.88, 128.03, 135.26,
NMR (400 MHz, DMSO-d6)
d
ppm: 2.21 (s, 3H, CH3), 2.42 (s, 3H,
139.01, 143.35, 145.20, 168.80; MS (ESI): m/z ¼ found 365.01 [Mþ];
calcd. 365.11. Anal. Calcd. for C18H15N5O4: C, 59.18; H, 4.14; N, 19.17.
Found: C, 58.94; H, 4.16; N, 19.09.
sulfonamidephenyleCH3), 6.29 (s, 2H, pyrroleeC3, C4eH), 7.18 (s,
2H, pyrroleeC2, C5eH), 7.36 (d, 2H, J ¼ 7.9, sulfonamidephenyleC3,
C5eH), 7.43 (d, 2H, J ¼ 8.6, phenyleC3, C5eH), 7.70 (d, 2H, J ¼ 8.6,
sulfonamidephenyleC2, C6eH), 7.86 (d, 2H, J ¼ 8.1, phenyleC2, C6e
4.7.25. 2-(1-(4-(1H-Pyrrol-1-yl)phenyl)ethylidene)
hydrazinecarbothioamide (4y)
H), 10.37 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6)
d ppm: 14.05,
21.06, 110.67, 118.62, 118.72, 127.20, 127.53, 129.20, 134.09, 136.20,
140.40, 143.05, 152.09; MS (ESI): m/z ¼ found 353.01 [Mþ]; calcd.
353.12. Anal. Calcd. for C19H19N3O2S: C, 64.57; H, 5.42; N, 11.89.
Found: C, 64.83; H, 5.40; N, 11.94.
(Yield 79%). mp 256e258 ꢃC; FTIR (KBr): 3414, 3263 (NH), 2924,
2856 (AreH), 1605 (C]N) cmꢀ1 1H NMR (400 MHz, DMSO-d6)
;
d
ppm: 2.30 (s, 3H, CH3), 6.24 (s, 2H, pyrroleeC3, C4eH), 7.16 (s, 2H,
pyrroleeC2, C5eH), 7.42 (d, 2H, J ¼ 8.5, phenyleC3, C5eH), 7.87 (d,