10.1002/cmdc.202000055
ChemMedChem
FULL PAPER
(C=O); MS: m/z=304.36 [M]+, 306.0 [M+2]; Anal. for C14H9FN2OS2: calcd:
ppm): δ=6.40 (t, 1H, thiophene C-4), 7.01 (d, J = 7.4, 1H, thiophene C-3),
7.18 (d, J = 7.3, 2H, Ar C-3, Ar C-5), 7.20 (d, J = 7.1, 2H, Ar C-2, Ar C-6),
7.38 (s, 1H, –C=CH), 7.43 (d, J = 7.2, 1H, thiophene C-5), 8.21 (s, 1H,
thiazolidinone NH); 13C NMR (CDCl3, 100 MHz, ppm): δ=115.34 (furan C-
3), 118.56 (furan C-4), 121.89, 144.93 (C=C), 123.74 (Ar C-2, Ar C-6),
132.01 (Ar C-3, Ar C-5), 134.23 (Ar C-4), 140.87 (furan C-5), 147.38 (Ar
C-1), 154.08 (furan C-2), 163.22 (C=N), 168.35 (C=O); MS: m/z=304.0
[M]+, 306.3 [M+2]; Anal. for C14H9ClN2O2S: calcd: C 56.94, H 3.82, N
8.85, found: C 56.92, H 3.87, N 8.89.
C 55.25, H 2.98, N 9.20, found: C 55.20, H 3.02, N 9.18.
2-(4-Methoxyphenylimino)-5-(thiophen-2-ylmethylene)thiazolidin-4-one
(10): IR (KBr, cm-1): ʋ=701.28 (C-S str), 1228.19 (C-N str), 1310.27 (C-O
str), 1490.59 (C=C aliphatic str), 1551.60 (C=C aromatic str), 1613.63
(C=N str), 1670.04 (C=O str), 2952.34 (C-H aliphatic str), 3082.5 (C-H
aromatic str), 3284.78 (N-H str); 1H NMR (CDCl3, 400 MHz, ppm): δ=3.68
(s, 3H, OCH3), 6.89 (d, J = 6.7, 2H, Ar C-3, Ar C-5), 7.25 (d, J = 6.9, 2H,
Ar C-2, Ar C-6), 7.29 (s, 1H, –C=CH), 7.39 (t, 1H, thiophene C-4), 7.57 (d,
J = 6.8, 1H, thiophene C-5), 7.72 (d, J = 7.0, 1H, thiophene C-3), 8.17 (s,
1H, thiazolidinone NH); 13C NMR (CDCl3, 100 MHz, ppm): δ=56.12
(OCH3), 119.63 (Ar C-3, Ar C-5), 121.90, 144.13 (C=C), 123.93 (Ar C-2,
Ar C-6), 128.10 (thiophene C-3), 132.41 (thiophene C-4), 135.18
(thiophene C-5), 136.28 (thiophene C-2), 145.02 (Ar C-1), 157.26 (Ar C-
4), 163.45 (C=N), 168.27 (C=O); MS: m/z=316.0 [M]+; Anal. for
C15H12N2O2S2: calcd: C 56.94, H 3.82, N 8.85, found: C 56.92, H 3.87, N
8.89.
2-(4-Fluorophenylimino)-5-(furan-2-ylmethylene)thiazolidin-4-one (14): IR
(KBr, cm-1): ʋ=702.16 (C-S str), 1124.36 (C-F str), 1225.32 (C-N str),
1313.54 (C-O str), 1487.26 (C=C aliphatic str), 1545.60 (C=C aromatic
str), 1625.15 (C=N str),1662.35 (C=O str), 2923.25 (C-H aliphatic str),
3119.09 (C-H aromatic str), 3292.71 (N-H str); 1H NMR (CDCl3, 400 MHz,
ppm): δ=6.58 (t, 1H, furan C-4), 6.99 (d, J = 7.0, 1H, furan C-3), 7.19 (d,
J = 7.2, 2H, Ar C-2, Ar C-6), 7.28 (d, J = 7.2, 2H, Ar C-3, Ar C-5), 7.42 (s,
1H, –C=CH), 7.92 (d, J = 7.4, 1H, furan C-5), 8.07 (s, 1H, thiazolidinone
NH); 13C NMR (CDCl3, 100 MHz, ppm): δ=110.68 (furan C-4), 113.25
(furan C-3), 119.45 (Ar C-3, Ar C-5), 121.90, 143.71 (C=C), 124.56 (Ar C-
2, Ar C-6), 144.04 (furan C-5), 146.37 (Ar C-1), 152.61 (furan C-2),
159.95 (Ar C-4), 163.17 (C=N), 168.12 (C=O); MS: m/z=288.6 [M]+, 290.3
[M+2]; Anal. for C14H9FN2O2S: calcd: C 58.33, H 3.15, N 9.72, found: C
58.32, H 3.19, N 9.69.
5-(Thiophen-2-ylmethylene)-2-(p-tolylimino)thiazolidin-4-one (11): IR (KBr,
cm-1): ʋ=701.87 (C-S str), 1227.53 (C-N str), 1508.61 (C=C aliphatic str),
1593.53 (C=C aromatic str), 1623.54 (C=N str), 1687.53 (C=O str),
2934.54 (C-H aliphatic str), 3082.79 (C-H aromatic str), 3247.50 (N-H
1
str); H NMR (CDCl3, 400 MHz, ppm): δ=2.43 (s, 3H, CH3), 6.99 (d, J =
6.9, 2H, Ar C-3, Ar C-5), 7.18 (d, J = 7.1, 2H, Ar C-2, Ar C-6), 7.37 (t, 1H,
thiophene C-4), 7.46 (s, 1H, –C=CH), 7.63 (d, J = 6.6, 1H, thiophene C-
3), 7.69 (d, J = 6.7, 1H, thiophene C-5), 8.19 (s, 1H, thiazolidinone NH);
13C NMR (CDCl3, 100 MHz, ppm): δ=25.73 (CH3), 120.87, 126.38
(thiophene C-3), 124.52 (Ar C-2, Ar C-6), 130.12 (thiophene C-4), 131.65
(Ar C-3, Ar C-5), 133.25 (thiophene C-5), 137.91 (thiophene C-2), 138.08
(Ar C-4), 143.52 (C=C), 147.03 (Ar C-1), 167.24 (C=O), 162.95 (C=N);
MS: m/z=300.1 [M]+; Anal. for C15H12N2OS2: calcd: C 59.97, H 4.03, N
9.33, found: C 60.02, H 4.08, N 9.30.
5-(Furan-2-ylmethylene)-2-(4-methoxyphenylimino)thiazolidin-4-one (15):
IR (KBr, cm-1): ʋ=701.25 (C-S str), 1223.12 (C-N str), 1311.64 (C-O str),
1627.14 (C=N str), 1514.90 (C=C aliphatic str), 1548.13 (C=C aromatic
str), 1675.19 (C=O str), 2979.25 (C-H aliphatic str), 3083.28 (C-H
aromatic str), 3372.96 (N-H str); 1H NMR (CDCl3, 400 MHz, ppm): δ=3.68
(s, 3H, OCH3), 6.57 (d, J = 6.9, 2H, Ar C-3, Ar C-5), 6.71 (t, 1H, furan C-
4), 7.03 (d, J = 6.8, 1H, furan C-3), 7.23 (d, J = 7.0, 2H, Ar C-2, Ar C-6),
7.37 (s, 1H, –C=CH), 7.95 (d, J = 7.3, 1H, furan C-5), 8.31 (s, 1H,
thiazolidinone NH); 13C NMR (CDCl3, 100 MHz, ppm): δ=54.37 (OCH3),
110.77 (Ar C-3, Ar C-5), 114.21 (furan C-3), 115.43 (furan C-4), 122.95,
143.09 (C=C), 124.26 (Ar C-2, Ar C-6), 142.15 (Ar C-1), 146.03 (furan C-
5), 152.99 (furan C-2), 158.63 (Ar C-4), 163.34 (C=N), 168.15 (C=O);
MS: m/z=300.7 [M]+; Anal. for C15H12N2O3S: calcd: C 59.99, H 4.03, N
9.33, found: C 60.03, H 4.08, N 9.30.
2-(4-Nitrophenylimino)-5-(thiophen-2-ylmethylene)thiazolidin-4-one (12):
IR (KBr, cm-1): ʋ=702.45 (C-S str), 1216.59 (C-N str), 1325.81, 1527.34
(NO2 str), 1549.49 (C=C aromatic str), 1589.00 (C=C aliphatic str),
1606.02 (C=N str), 1660.94 (C=O str), 2954.53 (C-H aliphatic str),
3061.84 (C-H aromatic str), 3293.60 (N-H str); 1H NMR (CDCl3, 400 MHz,
ppm): δ=7.33 (t, 1H, thiophene C-4), 7.50 (s, 1H, –C=CH), 7.66 (d, J =
7.3, 1H, thiophene C-5), 7.78 (d, J = 7.0, 1H, thiophene C-3), 7.85 (d, J =
7.4, 2H, Ar C-2, Ar C-6), 8.23 (s, 1H, thiazolidinone NH), 8.37 (d, J = 7.2,
2H, Ar C-3, Ar C-5); 13C NMR (CDCl3, 100 MHz, ppm): δ=120.89, 143.23
(C=C), 124.19 (Ar C-3, Ar C-5), 127.35 (Ar C-2, Ar C-6), 129.10
(thiophene C-3), 132.23 (thiophene C-4), 136.53 (thiophene C-5), 136.89
(thiophene C-2), 148.24 (Ar C-4), 149.92 (Ar C-1), 162.16 (C=N), 166.99
(C=O); MS: m/z=332.0 [M]+; Anal. for C14H9N3O3S2: calcd: C 50.74, H
2.74, N 12.68, found: C 50.70, H 2.73, N 12.60.
5-(Furan-2-ylmethylene)-2-(p-tolylimino)thiazolidin-4-one (16): IR (KBr,
cm-1): ʋ=703.58 (C-S str), 1265.02 (C-N str), 1315.22 (C-O str), 1537.87
(C=C aliphatic str), 1594.34 (C=C aromatic str), 1607.80 (C=N str),
1665.69 (C=O str), 2995.54 (C-H aliphatic str), 3073.68 (C-H aromatic
1
str), 3303.92 (N-H str); H NMR (CDCl3, 400 MHz, ppm): δ=2.46 (s, 3H,
CH3), 6.75 (t, 1H, furan C-4), 7.05 (d, J = 6.8, 1H, furan C-3), 7.14 (d, J =
7.3, 2H, Ar C-2, Ar C-6), 7.22 (d, J = 7.2, 2H, Ar C-3, Ar C-5), 7.39 (s, 1H,
–C=CH), 7.86 (d, J = 7.3, 1H, furan C-5), 8.11 (s, 1H, thiazolidinone NH);
13C NMR (CDCl3, 100 MHz, ppm): δ=26.31 (CH3), 113.33 (furan C-3),
116.41 (furan C-4), 121.38, 143.30 (C=C), 123.68 (Ar C-2, Ar C-6),
132.82 (Ar C-3, Ar C-5), 138.71 (Ar C-4), 145.94 (furan C-5), 148.15 (Ar
C-1), 151.92 (furan C-2), 164.32 (C=N), 167.97 (C=O); MS: m/z=285.0
[M]+; Anal. for C15H12N2O2S: calcd: C 63.36, H 4.25, N 9.85, found: C
63.39, H 4.27, N 9.80.
2-(4-Chlorophenylimino)-5-(furan-2-ylmethylene)thiazolidin-4-one (13): IR
(KBr, cm-1): ʋ=704.32 (C-S str), 756.72 (C-Cl str), 1223.37 (C-N str),
1310.03 (C-O str), 1508.77 (C=C aliphatic str), 1566.68 (C=C aromatic
str), 1626.31 (C=N str),1669.62 (C=O str), 2950.01 (C-H aliphatic str),
3123.12 (C-H aromatic str), 3274.04 (N-H str); 1H NMR (CDCl3, 400 MHz,
13
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