Journal of the Iranian Chemical Society
1
obtained product was ꢁltered and washed with excess of
distilled water and recrystallized with ethanol.
1456 (CH ), 1365 (CH ), 946 (C–S); H NMR (300 MHz, CDCl )
2
3
3
δ 14.12 (s, 1H), 7.25 (d, J=7.5 Hz, 2H), 6.91 (d, J=7.5 Hz, 2H),
−1
Yellow powder, yield 87%, m.p. 195–197 °C, ATR (cm )
5.03 (s, 2H), 3.60 (q, J=6.0 Hz, 2H), 2.92 (s, 4H), 2.32 (s, 1H), 1.22
13
3
418–3309 (NH , NH), 2933 (C–Haliph.), 2550 (SH), 1780,
(t, J=6.0 Hz, 6H); C NMR (75 MHz, CDCl ) δ 177.8, 165.1,
2
3
1
726 (C=O imide), 1684 (C=O), 1621, 1611 (C=N), 1450
152.2, 149.8, 143.2, 130.3, 121.8, 110.1, 46.3, 32.6, 28.4, 13.0; MS
−1
1
+
(
CH ), 1212 (C–S) cm ; H NMR (CDCl ) δ 14.11 (s, 1H),
for C H N O S (m/z, APCI): calcd 386.15 (M ), found 387.21
2
3
18 22
[M+H] .
6
2
1
3
+
5
1
.80 (s, 2H), 5.03 (s, 2H), 4.18 (s, 4H); CNMR(CDCl ) δ
3
76.7, 167.5, 148.7, 40.1, 33.1.
(
E) ‑ 1 ‑ ( ( 5 ‑ m e rc a p to ‑ 4 ‑ ( ( 4 ‑ m e t h ox y b e n z y l i d e n e )
General Procedure for the Synthesis of (E)‑1‑((4‑(aryliden
eamino)‑5‑mercapto‑4H‑1,2,4‑triazol‑3‑yl)methyl)pyrroli‑
dine‑2,5‑diones (T1–T10)
amino)‑4H‑1,2,4‑triazol‑3‑yl)methyl) pyrolidine‑2,5‑dione
(T4) Yield 88%, R 0.59, m.p. 181–183 °C, ATR (Neat,
f
−
1
cm ) ̃ꢀ : 3127 (C=C–H), 2963, 2858 (C–H), 2555(SH),
max
1
845, 1783 (C–N, imide), 1605 (Aromatic, C=C ),
str
1
-((4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)methyl)pyr-
1635(C=N), 1620 (C=N), 1455 (CH ), 1212 (C–O), 1369
2
1
rolidine-2,5-dione (0.34 g, 1.5 mmol) and acetic acid (4–5
drops) were added to a solution of aryl aldehydes (1.5 mmol)
in dry ethanol (10 mL). The mixture was reꢃuxed for 3–4 h
and was monitored by TLC until the completion of reaction
of reaction obtained. Solvent evaporated to dryness to give
a residue, which was puriꢁed by recrystallization. This pro-
cedure was applied for all the compounds [50].
(CH ), 946 (C–S); H NMR (300 MHz, CDCl ) δ 14.08
3
3
(s, 1H), 7.37 (d, J=7.5 Hz, 2H), 7.01 (d, J=7.5 Hz, 2H),
1
3
5.03 (s, 2H), 3.81 (s, 3H), 2.92 (s, 4H), 2.27 (s, 1H);
C
NMR (75 MHz, CDCl ) δ 177.8, 165.1, 161.0, 149.8, 143.2,
3
129.6, 127.1, 114.5, 56.0, 32.6, 28.4; MS for C H N O S
1
5
15
5
3
+
+
(m/z, APCI): calcd 354.09 (M ), found 348.09 [M+H] .
(
E)‑1‑((4‑((2‑hydroxy‑3‑methoxybenzylidene)amino)‑
(
E)‑1‑((4‑(benzylideneamino)‑5‑mercapto‑4H‑1,2,4‑tria‑
5‑mercapto‑4H‑1,2,4‑triazol‑3‑yl) methyl)pyrrolidine‑2,5‑
zol‑3‑yl)methyl)pyrrolidine‑2,5‑dione (T1) Yield 84%, R
dione (T5) Yield 85%, R 0.49, m.p. 192–195 °C, ATR
f
f
−1
−1
0
.8, m.p. 163–165 °C, ATR (Neat, cm ) ̃ꢀ : 3117 (C=C–
(Neat, cm ) ̃ꢀ : 3123 (C=C–H), 2957, 2843 (C–H), 2549
max
max
H), 2958, 2847 (C–H), 2594 (SH), 1843, 1780 (C–N, imide),
(SH), 1842, 1779 (C–N, imide), 1601 (Aromatic, C=C ),
str
1
603 (Aromatic, C=C ), 1633 (C=N), 1618 (C=N), 1455
1629 (C=N), 1616 (C=N), 1451 (CH ), 1215 (C–O), 1371
str
2
1
1
(
CH ), 946(C–S); H NMR (300 MHz, CDCl ) δ 14.13 (s,
(CH ), 946 (C–S); H NMR (300 MHz, CDCl ) δ 14.10 (s,
2
3
3
3
1
8
H), 8.33 (d, J=8.5 Hz, 1H), 8.10 (d, J=8.5 Hz, 1H),7.94–
1H), 6.99–6.75 (m, 3H), 5.03 (s, 2H), 4.44 (s, 1H), 3.81 (s,
1
3
13
5 (m, 3H), 5.03 (s, 2H), 2.92 (s, 4H); C NMR (75 MHz,
3H), 2.92 (s, 4H), 2.26 (s, 1H); C NMR (75 MHz, CDCl )
3
CDCl ) δ 177.8, 167.5, 162.5, 160.4, 150.0, 146.8, 138.4,
δ 177.8, 165.1, 148.6, 148.2, 143.2, 140.0, 123.2, 120.6,
3
1
35.9, 131.8, 130.2, 129.8, 129.1, 124.6, 123.9, 33.1, 28.4,
119.5, 116.4, 56.8, 32.6, 28.4; MS for C H N O S (m/z,
1
5
15
5
4
+
+
+
MS for C H N O S (m/z, APCI): calcd 315.08 (M ),
APCI): calcd 361.08 (M ), found 362.05 [M+2H] .
1
4
13
5
2
+
found 316.16 [M+2H] .
(
E) ‑ 1 ‑ ( ( 5 ‑ m e r c a p t o ‑ 4 ‑ ( ( 3 ‑ n i t r o b e n z y l i d e n e )
(
E)‑1‑((4‑((4‑(dimethylamino)benzylidene)amino)‑
amino)‑4H‑1,2,4‑triazol‑3‑yl)methyl) pyrolidine‑2,5‑dione
5
‑mercapto‑4H‑1,2,4‑triazol‑3‑yl) methyl)pyrrolidine‑2,5‑
(T6) Yield 83%, R 0.67, m.p. 167–168 °C, ATR (Neat,
f
−
1
dione (T2) Yield 87%, R 0.73, m.p. 172–173 °C, ATR
cm ) ̃ꢀ : 3119 (C=C–H), 2948, 2839 (C–H), 2547 (SH),
f
max
−1
(
Neat, cm ) ̃ꢀ : 3121 (C=C–H), 2960, 2851 (C–H), 2550
1841, 1780 (C–N, imide), 1598 (Aromatic, C=C ), 1630
max
str
(
SH), 1845, 1782 (C–N, imide), 1605 (Aromatic, C=C ),
(C=N), 1616 (C=N), 1553, 1351 (NO ), 1455 (CH ), 946
str
2
2
1
1
637 (C=N), 1620 (C=N), 1455 (CH ), 1367 (CH ), 946
(C–S); H NMR (300 MHz, CDCl ) δ 14.11 (s, 1H), 10.21
2
3
3
1
(
C–S); H NMR (300 MHz, CDCl ) δ 14.10 (s, 1H), 7.29 (d,
(s, 1H), 8.63 (s, 1H), 8.41 (d, J=7.5 Hz, 1H), 8.25 (d,
3
J=7.5 Hz, 2H), 6.82 (d, J=7.5 Hz, 2H), 5.03 (s, 2H), 2.92
J=7.0 Hz, 1H), 7.87 (dd, J=8, 7.5 Hz, 1H), 5.03 (s, 2H),
13
13
(
s, 6H), 2.27 (s, 4H); C NMR (75 MHz, CDCl ) δ 177.8,
4.18 (s, 4H), C NMR (75 MHz, CDCl ) δ 177.8, 167.5,
3
3
1
65.1, 154.5, 149.8, 143.2, 128.9, 121.4, 111.3, 41.9, 32.6,
162.5, 161.6, 148.7, 146.7, 135.3, 135.2, 134.1, 131.8,
+
2
8.4; MS for C H N O S (m/z, APCI): calcd 358.15 (M ),
127.3, 123.9, 123.0, 33.1, 28.4; MS for C H N O S (m/z,
16
18
6
2
14 12
6
4
+
+
+
found 359.09 [M+H] .
APCI): calcd 360.06 (M ), found 361.05 [M+H] .
(
E)‑1‑((4‑((4‑(diethylamino)benzylidene)amino)‑5‑
( E) ‑ 1 ‑ ( ( 5 ‑ m e r c a p t o ‑ 4 ‑ ( ( 4 ‑ n i t r o b e n z y l i d e n e )
amino)‑4H‑1,2,4‑triazol‑3‑yl)methyl) pyrolidine‑2,5‑dione
mercapto‑4H‑1,2,4‑triazol‑3‑yl) methyl)pyrrolidine‑2,5‑dione
−1
(T3) Yield 89%, R 0.65, m.p. 177–179 °C, ATR (Neat, cm ) ̃ꢀ (T7) Yield 81%, R 0.69, m.p. 174–176 °C, ATR (Neat,
f
f
−
1
:
3123 (C=C–H), 2961, 2853 (C–H), 2551(SH), 1844, 1781
cm ) ̃ꢀ : 3067 (C=C–H), 2915, 2847 (C–H), 2545(SH),
max
max
(C–N, imide), 1607 (Aromatic, C=C ), 1637(C=N), 1619 (C=N),
1596 (Aromatic, C=C ), 1621 (C=N), 1617 (C=N), 1551,
str
str
1
3