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140.0 (C’4), 143.7 (C=N), 144.8 (C7a), 149.9 (C3a), 165.1 ppm (C=O);
IR (KBr): n˜ =3190.37 (NÀH str.), 3088.14 (arom. CÀH str.), 2955.04
(CH2 str.), 1708.99 (C=O str.), 1600.97 (C=N str.), 1465.95 (C=C str.),
1101.39 (CÀOÀC str.), 866.07 cmÀ1 (CÀCl str.); Anal. for
C15H11Cl2N3O3: calcd: C 51.16, H 3.15, N 11.93, found: C 51.18, H
3.10, N 11.99.
C’6), 131.6 (C’’2, C’’6), 133.0 (C’’1), 133.1 (C’4), 133.5 (C’1), 135.7
(C’’4), 142.1 (C7a), 146.7 (C3a), 153.8 (C=N), 167.1 ppm (C=O); IR
(KBr): n˜ =3446.91, 3369.75 (NÀH str.), 3064.99 (arom. CÀH str.),
2895.25 (CH2 str.), 1658.84 (C=O str.), 1589.40 (C=N str.), 1487.17
(C=C str.), 1273.06 (CÀOÀC str.), 829.42 cmÀ1 (CÀCl str.); Anal. for
C21H16ClN3O3: calcd: C 64.05, H 4.09, N 10.67, found: C 64.01, H
4.13, N 10.62.
1-(2,6-Dichlorobenzylidene)-4-(benzo[1,3]dioxol-5-yl)semicarba-
zide (16): yield: 46.9%, mass: 352.17 gmolÀ1; mp: 92–948C; Rf:
4-(Benzo[1,3]dioxol-5-yl)-1-(bis(4-chlorophenyl)methylene)semi-
1
0.54; H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=3.62 (s, 2H,
carbazide (20): yield: 41.5%, mass: 428.87 gmolÀ1; mp: 203–
1
CH2), 5.94 (s, 1H, NH), 6.73 (s, 1H, benzene CH), 6.86 (d, J=7.5 Hz,
1H, benzene CH), 7.26 (d, J=7.3 Hz, 2H, Ar C3, Ar C5), 7.31 (dd, J=
7.9, 6.7 Hz, 1H, Ar C4), 7.56 (d, J=7.8 Hz, 1H, benzene CH), 8.52 (s,
1H, CH), 9.81 ppm (s, 1H, CONH); 13C NMR ([D6]DMSO, 75 MHz):
d=101.3 (C2), 108.0 (C4), 111.0 (C6), 111.7 (C7), 129.1 (C’3, C’5),
133.8 (C5), 134.2 (C’1), 142.7 (C’4), 146.3 (C’2, C’6), 147.0 (C=N),
147.2 (C7a), 152.8 (C3a), 167.9 ppm (C=O); IR (KBr): n˜ =3327.32,
3308.03 (NÀH str.), 3090.07 (arom. CÀH str.), 2995.55 (CH2 str.),
1705.13 (C=O str.), 1560.46 (C=N str.), 1487.17 (C=C str.), 1242.20
(CÀOÀC str.), 781.20 cmÀ1 (CÀCl str.); Anal. for C15H11Cl2N3O3: calcd:
C 51.16, H 3.15, N 11.93, found: C 51.23, H 3.20, N 11.88.
2058C; Rf: 0.49; H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=
3.39 (s, 2H, CH2), 5.90 (s, 1H, NH), 6.70 (d, J=8.1 Hz, 1H, benzene
CH), 7.09 (d, J=7.8 Hz, 1H, benzene CH), 7.13 (s, 1H, benzene CH),
7.55 (d, J=6.2 Hz, 4H, Ar C3, Ar C5, Ar’ C3, Ar’ C5), 7.89 (d, J=
6.6 Hz, 4H, Ar C2, Ar C6, Ar’ C2, Ar’ C6), 9.83 ppm (s, 1H, CONH);
13C NMR ([D6]DMSO, 75 MHz): d=101.3 (C2), 107.6 (C4), 111.5 (C6),
115.8 (C7), 128.7 (C’3, C’5, C’’3, C’’5), 128.8 (C5), 131.0 (C’2, C’6, C’’2,
C’’6), 131.1 (C’1, C’’1), 135.7 (C’4, C’’4), 142.9 (C7a), 146.9 (C3a),
154.7 (C=N), 166.5 ppm (C=O); IR (KBr): n˜ =3446.91, 3369.75 (NÀH
str.), 3064.99 (arom. CÀH str.), 2895.25 (CH2 str.), 1658.84 (C=O str.),
1589.40 (C=N str.), 1487.17 (C=C str.), 1273.06 (CÀOÀC str.),
829.42 cmÀ1 (CÀCl str.); Anal. for C21H15Cl2N3O3: calcd: C 58.89, H
3.53, N 9.81, found: C 58.85, H 3.59, N 9.84.
1-(2,5-Dimethoxybenzylidene)-4-(benzo[1,3]dioxol-5-yl)semicar-
bazide (17): yield: 40.4%, mass: 343.33 gmolÀ1; mp: 126–1288C;
1
Rf: 0.55; H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=3.29 (d,
4-(Benzo[1,3]dioxol-5-yl)-1-(2-oxoindolin-3-ylidene)semicarba-
J=5.6 Hz, 1H, benzene CH), 3.32 (s, 2H, CH2), 3.98 (s, 6H, OCH3),
6.05 (s, 1H, NH), 7.35 (s, 1H, benzene CH), 7.36 (d, J=6.6 Hz, 2H,
Ar C3, Ar C4), 7.38 (s, 1H, Ar C6), 7.41 (d, J=6.1 Hz, 1H, benzene
CH), 7.55 (s, 1H, CH), 9.93 ppm (s, 1H, CONH); 13C NMR ([D6]DMSO,
75 MHz): d=57.5 (OCH3), 101.3 (C2), 107.8 (C4), 111.0 (C’6), 111.5
(C6), 115.3 (C’3), 115.4 (C7), 117.8 (C’4), 118.2 (C’1), 130.2 (C5), 142.5
(C7a), 143.2 (C=N), 146.8 (C3a), 153.1 (C’2), 153.8 (C’5), 167.4 ppm
(C=O); IR (KBr): n˜ =3311.89, 3184.58 (NÀH str.), 3080.42 (arom. CÀH
str.), 2982.05 (CH2 str.), 1720.56 (C=O str.), 1545.03 (C=N str.),
1500.67 (C=C str.), 1242.20 cmÀ1 (CÀOÀC str.); MS: m/z=344.98
[M+1]+; Anal. for C17H17N3O5: calcd: C 59.47, H 4.99, N 12.24,
found: C 59.41, H 5.03, N 12.27.
zide (21): yield: 42.3%, mass: 324.29 gmolÀ1; mp: 158–1608C; Rf:
1
0.50; H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=3.38 (s, 2H,
CH2), 5.94 (s, 1H, NH), 6.81 (d, J=8.7 Hz, 1H, benzene CH), 6.89 (d,
J=8.1 Hz, 1H, benzene CH), 7.07 (dd, J=8.3, 7.8 Hz, 1H, isatinyl
CH), 7.16 (s, 1H, benzene CH), 7.26 (dd, J=8.1, 7.5 Hz, 1H, isatinyl
CH), 7.34 (d, J=6.4 Hz, 1H, isatinyl CH), 7.52 (d, J=6.9 Hz, 1H, isa-
tinyl CH), 8.28 (s, 1H, isatinyl NH), 9.79 ppm (s, 1H, CONH);
13C NMR ([D6]DMSO, 75 MHz): d=101.4 (C2), 108.5 (C4), 109.7 (C6),
111.7 (C7), 112.5 (isatinyl C’3a), 122.0 (isatinyl C’7), 128.0 (isatinyl
C’5), 128.5 (C5), 129.0 (isatinyl C’4), 131.9 (isatinyl C’6), 133.1 (C=N),
142.9 (C7a), 147.4 (isatinyl C’7a), 148.9 (C3a), 168.4 (C=O),
179.0 ppm (isatinyl C=O); IR (KBr): n˜ =3402.54, 3263.66 (NÀH str.),
3090.07 (arom. CÀH str.), 2920.32 (CH2 str.), 1699.34 (lactam C=O),
1622.19 (C=O str.), 1560.46 (C=N str.), 1489.10 (C=C str.),
1240.27 cmÀ1 (CÀOÀC str.); Anal. for C16H12N4O4: calcd: C 59.26, H
3.73, N 17.28, found: C 59.22, H 3.79, N 17.24.
4-(Benzo[1,3]dioxol-5-yl)-1-(diphenylmethylene)semicarbazide
(18): yield: 43.9%, mass: 359.38 gmolÀ1; mp: 168–1708C; Rf: 0.51;
1H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=3.52 (s, 2H, CH2),
5.95 (s, 1H, NH), 6.80 (d, J=6.9 Hz, 1H, benzene CH), 6.95 (d, J=
7.5 Hz, 1H, benzene CH), 7.21 (s, 1H, benzene CH), 7.30 (dd, J=7.4,
6.7 Hz, 3H, Ar’ C3, Ar’ C4, Ar’ C5), 7.35 (dd, J=7.8, 6.9 Hz, 3H, Ar
C3, Ar C4, Ar C5), 7.45 (d, J=6.8 Hz, 2H, Ar’ C2, Ar’ C6), 7.71 (d, J=
7.1 Hz, 2H, Ar C2, Ar C6), 9.99 ppm (s, 1H, CONH); 13C NMR
([D6]DMSO, 75 MHz): d=102.0 (C2), 104.4 (C4), 111.8 (C6), 116.3
(C7), 125.6 (C’3, C’5, C’’3, C’’5), 128.1 (C5), 128.4 (C’2, C’6, C’’2, C’’6),
128.6 (C’4, C’’4), 129.6 (C’1, C’’1), 142.6 (C7a), 146.8 (C3a), 147.8 (C=
N), 168.0 ppm (C=O); IR (KBr): n˜ =3327.32, 3309.96 (NÀH str.),
3032.20 (arom. CÀH str.), 2962.76 (CH2 str.), 1660.77 (C=O str.),
1568.18 (C=N str.), 1487.17 (C=C str.), 1251.84 cmÀ1 (CÀOÀC str.);
Anal. for C21H17N3O3: calcd: C 70.18, H 4.77, N 11.69, found: C
70.15, H 4.80, N 11.61.
4-(Benzo[1,3]dioxol-5-yl)-1-(5-chloro-2-oxoindolin-3-ylidene)se-
micarbazide (22): yield: 55.6%, mass: 358.74 gmolÀ1; mp: 70–
728C; Rf: 0.49; 1H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=
3.48 (s, 2H, CH2), 5.90 (s, 1H, NH), 6.81 (d, J=6.3 Hz, 1H, benzene
CH), 6.90 (d, J=7.8 Hz, 1H, benzene CH), 7.11 (s, 1H, benzene CH),
7.40 (d, J=6.1 Hz, 1H, isatinyl C7), 7.73 (s, 1H, isatinyl C4), 7.74 (d,
J=6.8 Hz, 1H, isatinyl C6), 8.19 (s, 1H, isatinyl NH), 9.76 ppm (s,
1H, CONH); 13C NMR ([D6]DMSO, 75 MHz): d=101.6 (C2), 108.0
(C4), 110.1 (C6), 112.8 (C7), 115.4 (isatinyl C’3a), 122.9 (isatinyl C’7),
128.3 (C5), 128.8 (isatinyl C’4), 130.9 (isatinyl C’5), 131.3 (isatinyl
C’6), 133.2 (C=N), 142.4 (isatinyl C’7a), 142.7 (C7a), 148.6 (C3a),
168.1 (C=O), 179.1 ppm (isatinyl C=O); IR (KBr): n˜ =3456.55,
3203.87 (NÀH str.), 3096.47 (arom. CÀH str.), 2928.04 (CH2 str.),
1716.70 (lactam C=O), 1654.98 (C=O str.), 1618.33 (C=N str.),
1473.66 (C=C str.), 1124.54 (CÀOÀC str.), 823.63 cmÀ1 (CÀCl str.);
Anal. for C16H11ClN4O4: calcd: C 53.57, H 3.09, N 15.62, found: C
53.57, H 3.13, N 15.67.
4-(Benzo[1,3]dioxol-5-yl)-1-((4-chlorophenyl)(phenyl)methylene)-
semicarbazide (19): yield: 53.7%, mass: 393.82 gmolÀ1; mp: 192–
1
1948C; Rf: 0.46; H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=
3.56 (s, 2H, CH2), 5.84 (s, 1H, NH), 6.68 (d, J=6.9 Hz, 1H, benzene
CH), 7.26 (d, J=6.3 Hz, 1H, benzene CH), 7.34 (s, 1H, benzene CH),
7.45 (dd, J=7.9, 7.0 Hz, 3H, Ar’ C3, Ar’ C4, Ar’ C5), 7.73 (d, J=
7.3 Hz, 2H, Ar C3, Ar C5), 7.89 (d, J=7.8 Hz, 2H, Ar’ C2, Ar’ C6),
8.12 (d, J=6.8 Hz, 2H, Ar C2, Ar C6), 9.63 ppm (s, 1H, CONH);
13C NMR ([D6]DMSO, 75 MHz): d=101.2 (C2), 107.3 (C4), 111.5 (C6),
115.8 (C7), 128.0 (C’3, C’5), 128.1 (C’’3, C’’5), 128.3 (C5), 128.8 (C’2,
4-(Benzo[1,3]dioxol-5-yl)-1-(5-nitro-2-oxoindolin-3-ylidene)semi-
carbazide (23): yield: 57.2%, mass: 369.29 gmolÀ1; mp: 186–
1
1888C; Rf: 0.54; H NMR ([D6]DMSO, D2O exchange, 300 MHz): d=
3.37 (s, 2H, CH2), 5.98 (s, 1H, NH), 6.84 (d, J=8.1 Hz, 1H, benzene
CH), 6.93 (d, J=7.2 Hz, 1H, benzene CH), 7.12 (s, 1H, benzene CH),
ChemMedChem 2016, 11, 1145 – 1160
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