S. Valizadeh, et al.
CarbohydratePolymers226(2019)115310
=8.0 Hz, 2H, Ar-H), 4.02 (t, J =7.6 Hz, 2 H), 3.74 (m, 8 H), 3.36 (t, J
=7.1 Hz, 2 H), 2.38 (s, 3 H). 13C NMR (100 MHz, CDCl3, δ, ppm):
166.8, 162.4, 141.0, 139.5, 133.1, 130.9, 128.0, 125.2, 122.3, 45.9,
43.9, 33.6, 28.2, 20.4. Anal. Calcd for C22H23N3O5S: C, 59.85; H, 5.25;
N, 9.52; Found: C, 59.96; H, 5.02; N, 9.68.
N-[3-(1,3-dioxoisoindolin-2-yl)-1-(piperidin-1-yl)propylidene]-4-
methylbenzene sulfonamide (4b): Pale yellow solid (0.4 g, 92%); m.p.
131–132 °C. FT‐IR (KBr, ν, cm−1): 3028, 2938, 1708, 1542. 1H NMR
(400 MHz, CDCl3, δ, ppm): 7.85 (m, 2H, Ar-H), 7.78 (d, J = 8.2, 2H,
Ar-H), 7.73 (m, 2H, Ar-H), 7.21 (d, J =8.1 Hz, 2H, Ar-H), 4.00 (t, J
=7.7 Hz, 2 H), 3.69 (m, 4 H), 3.35 (t, J =7.1 Hz, 2 H), 2.37 (s, 3 H),
1.70 (b, 5 H), 1.61 (b, 2 H). 13C NMR (100 MHz, CDCl3, δ, ppm):
166.8, 161.8, 140.6, 140.1, 133.2, 133.0, 131.0, 128.0, 125.2, 122.5,
122.3, 46.7, 45.1, 33.7, 28.5, 26.4, 25.7, 24.1, 23.1, 20.4. Anal. Calcd
for C23H25N3O4S: C, 62.85; H, 5.73; N, 9.56; Found: C, 62.71; H, 5.81;
N, 9.39.
N-[3-(1,3-dioxoisoindolin-2-yl)-1-(pyrrolidin-1-yl)propylidene]-4-
methylbenzene sulfonamide (4c): Pale yellow solid (0.38 g, 90%); yield
92%; m.p 131–132 °C. FT‐IR (KBr, ν, cm−1): 2927, 2859, 1706, 1542,.
1H NMR (400 MHz, CDCl3, δ, ppm): 7.83 (dd, J = 5.4, 3.0 Hz, 2H, Ar-
H), 7.78 (d, J =8.2 Hz, 2H, Ar-H), 7.72 (dd, J = 5.4, 3.0 Hz, 2H, Ar-H),
7.21 (d, J =8.1 Hz, 2H, Ar-H), 4.00 (t, J =7.6 Hz, 2 H), 3.68 (m, 4 H),
3.35 (t, J =7.1 Hz, 2 H), 2.37 (s, 3 H), 1.60–1.69 (m, 6 H). 13C NMR
(100 MHz, CDCl3, δ, ppm): 166.8, 161.8, 140.6, 140.6, 140.2, 140.1,
132.9, 132.9, 130.9, 127.9, 125.2, 122.2, 46.7, 45.1, 33.7, 28.5, 25.7,
24.1, 23.0, 20.3, 20.3. Anal. Calcd for C22H23N3O4S: C, 62.10; H, 5.45;
N, 9.88; Found: C, 62.21; H, 5.38; N, 9.72.
3-(1, 3-dioxoisoindolin-2-yl)-N, N-diethyl-N'-tosylpropanimidamide
(4d): White solid (0.4 g, 95%); m.p 157–160 °C. FT‐IR (KBr, ν, cm−1):
3031, 2978, 1707, 1547. 1H NMR (400 MHz, CDCl3, δ, ppm): 7.85 (m,
4H, Ar-H), 7.73 (m, 2H, Ar-H), 7.23 (d, J =8 Hz, 2H, Ar-H), 4.07 (t, J
=7.7 Hz, 2 H), 3.57 (q, J =7.0 Hz, 2 H), 3.48 (q, J =7.0 Hz, 2 H), 3.30
(t, J =7.8 Hz), 2.38 (s, 3 H), 1.26 (t, J =7.0 Hz, 3 H), 1.13 (t, J
=7.0 Hz, 3 H). 13C NMR (100 MHz, CDCl3, δ, ppm): 166.7, 161.9,
140.6, 140.1, 133, 130.9, 127.9, 125.1, 122.3, 42.4, 42.2, 34.0, 28.5,
20.4, 13.1, 10.9. Anal. Calcd for C22H25N3O4S: C, 61.81; H, 5.89; N,
9.83; Found: C, 61.74; H, 5.71; N, 9.69.
3-(1,3-dioxoisoindolin-2-yl)-N,N-dipropyl-N'-tosylpropanimidamide
(4e): White solid (0.42 g, 93%); m.p. 131–132 °C. FT‐IR (KBr, ν,
cm−1): 3036, 2967, 1709, 1545. 1H NMR (400 MHz, CDCl3, δ, ppm):
7.85 (m, 4H, Ar-H), 7.73 (m, 2H, Ar-H), 7.23 (d, J = 8.0, 2H, Ar-H),
4.07 (t, J =7.4 Hz, 2 H), 3.47 (t, J =7.8 Hz, 2 H), 3.29–3.38 (m, 4 H),
2.38 (s, 3 H), 1.55–1.68 (m, 4 H), 0.98 (t, J =7.3 Hz, 3 H), 0.84 (t, J
=7.3 Hz, 3 H). 13C NMR (100 MHz, CDCl3, δ, ppm): 166.7, 162.2,
140.6, 140.2, 133.0, 130.9, 127.9, 125.1, 122.3, 49.7, 49.7, 34.0, 28.5,
21.3, 20.4, 19.0, 10.3, 10.0. Anal. Calcd for C24H29N3O4S: C, 63.28; H,
6.42; N, 9.22; Found: C, 63.07; H, 6.56; N, 9.41.
N,N-dibutyl-3-(1,3-dioxoisoindolin-2-yl)-N'-tosylpropanimidamide
(4f): White solid (0.48 g, 90%); m.p. 131–132 °C. FT‐IR (KBr, ν,
cm−1): 2951, 2865, 1715, 1551, 1304. 1H NMR (400 MHz, CDCl3, δ,
ppm): 7.84 (m, 4H, Ar-H), 7.72 (m, 2H, Ar-H), 7.23 (d, J =8.0 Hz, 2H,
Ar-H), 4.07 (t, J =7.9 Hz, 2 H), 3.48 (t, J =7.9 Hz, 2 H), 3.39 (t, J
=7.7 Hz, 2 H), 3.32 (t, J =7.3 Hz, 2 H), 2.38 (s, 3 H), 1.47–1.63 (m,
4 H), 1.38 (m, 2 H), 1.23 (m, 2 H), 0.95 (t, J =7.1 Hz, 3 H), 0.84 (t, J
=7.3 Hz, 3 H). 13C NMR (100 MHz, CDCl3, δ, ppm): 166.7, 162.0,
140.5, 140.1, 133.0, 130.8, 127.9, 125.1, 122.3, 48.0, 47.9, 34.0, 30.1,
28.5, 27.7, 20.3, 19.1, 18.9, 12.7, 12.6. Anal. Calcd for C26H33N3O4S: C,
64.57; H, 6.88; N, 8.69; Found: C, 64.41; H, 6.75; N, 8.73.
C, 69.67; H, 5.30; N, 7.62; Found: C, 69.77; H, 5.33; N, 7.57.
3-(1,3-dioxoisoindolin-2-yl)-N,N-diphenyl-N'-tosylpropanimidamide
(4 h): White solid (0.49 g, 95%); m.p.177–180 °C. IR (KBr, ν, cm−1):
3030, 2953, 1712, 1556. 1H NMR (400 MHz, CDCl3, δ, ppm): 7.80
(dd, J = 5.3, 3.1 Hz, 2H, Ar-H), 7.68 (dd= J = 5.4, 3.0 Hz, 2H, Ar-H),
7.42 (d, J =8.2 Hz, 2H, Ar-H), 7.26 (b, 10H, Ar-H), 7.05 (d, J=8.1 Hz,
2H, Ar-H), 4.03 (t, J =5.1 Hz, 2 H), 3.52 (t, J =6.6 Hz, 2 H), 2.32 (S,
3 H). 13C NMR (100 MHz, CDCl3, δ, ppm): 167.0, 164.4, 140.7, 139.2,
132.7, 131.2, 128.9, 127.9, 127.7, 127.4, 126.1, 125.0, 122.1, 34.1,
29.6, 20.3. Anal. Calcd for C30H25N3O4S: C, 68.82; H, 4.81; N, 8.03;
Found: C, 68.73; H, 4.79; N, 8.11.
3-(1,3-dioxoisoindolin-2-yl)-N-phenyl-N'-tosylpropanimidamide (4i):
White solid (0.4 g, 90%, E/Z (87:13)); m.p. 167–169 °C. FT‐IR (KBr, ν,
cm−1): 3353, 3058, 2948, 1700, 1557, 1537. 1H NMR (400 MHz,
CDCl3, δ, ppm): 9.91 (s, 1 H), 7.81 (d, J =8.2 Hz, 2H, Ar-H), 7.66–7.74
(m, 4H, Ar-H), 7.53 (b, 0.36H, Ar-H), 7.35 (m, 3H, Ar-H), 7.22 (m, 4 H),
4.18 (b, 0.3HZ), 3.87 (t, J =7.3 Hz, 2HE), 3.48 (b, 0.3HZ), 2.64 (t,
J=7.3 Hz, 2HE), 2.41 (s, 3 H). 13C NMR (100 MHz, CDCl3, δ, ppm):
166.8, 163.1, 141.9, 134.9, 133.3, 132.8, 130.8, 128.7, 128.2, 127.3,
125.7, 125.4, 122.2, 120.7, 33.4, 30.9, 20.5. Anal. Calcd for
C
24H21N3O4S: C, 64.42; H, 4.73; N, 9.39; Found: C, 64.51; H, 4.71; N,
9.44.
N-(4-chlorophenyl)-3-(1,3-dioxoisoindolin-2-yl)-N'-tosyl propanimida-
mide (4 j): Pale yellow solid (0.44 g, 92%; E/Z (75:25)); m.p.
131–132 °C. FT‐IR (KBr, ν, cm−1): 3353, 3217, 1769, 1700, 1577,
1537. 1H NMR (400 MHz, CDCl3, δ, ppm): 9.84 (s, 1 H), 7.85 (b, 0.7H,
Ar-H), 7.78 (d, J =8.2 Hz, 2.8H, Ar-H), 7.69–7.73 (m, 4.8H, Ar-H), 7.48
(b, 0.68H, Ar-H), 7.34 (d, J =8.1 Hz, 2H, Ar-H), 7.23 (d, J =7.6 Hz,
3.2H, Ar-H), 7.16 (d, J =8.2 Hz, 2H, Ar-H), 4.17 (b, 0.69HZ), 3.86 (t, J
=7.1 Hz, 2HE), 3.48 (b, 0.69HZ), 2.62 (t, J =7 Hz, 2HE), 2.41 (s,
4..1 H). 13C NMR (100 MHz, CDCl3, δ, ppm): 162.8, 133.4, 132.9,
130.8, 128.9, 128.3, 127.8, 127.1, 125.4, 122.2, 33.3, 30.9, 20.5. Anal.
Calcd for C24H20ClN3O4S: C, 59.81; H, 4.18; N, 8.72; Found: C, 59.72;
H, 4.22; N, 8.61.
3-(1,3-dioxoisoindolin-2-yl)-N-(4-nitrophenyl)-N'-tosylpropanimida-
mide (4k): White solid (0.48 g, 95%); m.p. 131–132 °C. FT‐IR (KBr, ν,
cm−1): 3332, 3119, 2937, 1772, 1702, 1609, 1545. 1H NMR
(400 MHz, CDCl3, δ, ppm): 9.10 (b, 0..62 H), 8.16 (b, 2 H), 7.74–7.83
(m, 7.8H, Ar-H), 7.26 (m, 3H, Ar-H), 4.15 (b, 1..7 H), 3.53 (b, 1..38 H),
2.43 (s, 3..1 H). 13C NMR (100 MHz, CDCl3, δ, ppm): 133.5, 130.6,
128.4, 125.4, 123.8, 122.6, 33.4, 20.5. Anal. Calcd for C24H20N4O6S: C,
58.53; H, 4.09; N, 11.38; Found: C, 58.61; H, 4.17; N, 11.45.
3-(1,3-dioxoisoindolin-2-yl)-N-isopropyl-N'-tosylpropanimidamide
(4 l): White solid (0.37 g, 90%, E/Z (53:47)); m.p. 160–162 °C. FT‐IR
(KBr, ν, cm−1): 3361, 2970, 2875, 1705, 1562. 1H NMR (400 MHz,
CDCl3, δ, ppm): 8.15 (b, 0.9.7 H), 7.69–7.83 (m, 14.9H, Ar-H), 7.22 (t,
J =9.2 Hz, 4.7H, Ar-H), 6.46 (b, 1..3 H), 4.02–4.12 (m, 4..5 H), 3.94 (t,
J =7.7 Hz, 2..1 H), 3.76–3.81 (m, 1 H), 3.23 (t, J =5.9 Hz, 2..8 H), 2.75
(t, J =7.5 Hz, 2 H), 2.38 (s, 7.2HE,Z), 1.91 (b, 0..36 H), 1.26 (d, J
=6.4 Hz, 6HZ), 1.09 (d, J =6.5 Hz, 8.7HE). 13C NMR (100 MHz,
CDCl3,δ, ppm): 167.1, 166.8, 162.6, 162.3, 141.5, 140.8, 139.8, 138.3,
133.2, 132.9, 130.8, 130.7, 128.1, 128.0, 125.1, 122.3, 122.2, 45.1,
42.9, 33.7, 33.4, 32.2, 30.1, 22.4, 20.5, 20.4, 20.3. Anal. Calcd for
C
21H23N3O4S: C, 61.00; H, 5.61; N, 10.16; Found: C, 61.23; H, 5.55; N,
10.31.
3-(1,3-dioxoisoindolin-2-yl)-N-(1-phenylethyl)-N'-tosylpropanimida-
mide (4 m): White solid (0.44 g, 92%, E/Z (53:47)); m.p. 131–132 °C.
FT‐IR (KBr, ν, cm−1): 3341, 3035, 2976, 2927, 1775, 1707, 1554. 1H
NMR (400 MHz, CDCl3, δ, ppm): 8.60 (b, 0.89HZ), 7.64–7.82 (m,
12.8H, Ar-H), 7.17–7.33 (m, 15.7H, Ar-H), 6.77 (b, 1HE), 5.05 (m, 1 H),
4.76 (m, 0..96 H), 4.05 (t, J=5.9 Hz, 2..1 H), 3.79–3.88 (m, 2 H),
3.18–3.36 (m, 2..2 H), 2.86–2.94 (b, 0.3.1 H), 2.73–2.81 (m, 0.9.8 H),
2.46 (m, 1 H), 2.39 (s, 6.3HE,Z), 1.56 (d, J =6.9 Hz, 3HZ), 1.43 (d, J
=6.8 Hz 3.4HZ), 13C NMR (100 MHz, CDCl3,δ, ppm): 167.2, 166.8,
163.3, 162.5, 141.7, 140.8, 133.2, 132.9, 130.7, 128.2, 128.1, 127.9,
127.5, 126.9, 126.4, 125.3, 125.2, 124.2, 122.4, 122.2, 52.8, 50.4,
N,
N-dibenzyl-3-(1,3-dioxoisoindolin-2-yl)-N'-tosylpropanimidamide
(4 g): White solid (0.5 g, 92%); m.p. 184–186 °C. FT‐IR (KBr, ν, cm−1):
3025, 2929, 1711, 1544. 1H NMR (400 MHz, CDCl3, δ, ppm): 7.86 (m,
4H, Ar-H), 7.74 (m, 2H, Ar-H), 7.18–7.43 (m, 13H, Ar-H), 4.85 (s, 2 H),
4.77 (s, 2 H), 4.17 (t, J =7.5 Hz, 2 H), 3.49 (t, J =7.5 Hz, 2 H), 2.43 (s,
3 H). 13C NMR (100 MHz, CDCl3, δ, ppm): 166.6, 164.0, 140.9, 139.7,
134.7, 134.0, 133.0, 130.8, 128.1, 128.0, 127.7, 127.1, 127.0, 126.7,
125.3,122.3, 50.1, 49.8, 33.8, 28.8, 20.4. Anal. Calcd for C32H29N3O4S:
3