Research Article
MedChemComm
phthalimide), 7.96–8.00 (m, 2H, phthalimide), 8.12 (d, 1H, J =
2.0 Hz, ArH), 12.70 (s, 1H, NH); 13C NMR (d6-DMSO, 100
MHz) δ: 67.5, 119.2, 124.3, 125.1, 126.8, 128.1, 129.6, 131.6,
135.2, 135.7, 141.3, 150.3, 167.1, 167.6, 167.8; HRMS (ESI)
calcd for [M − H]− C19H10N3O7S: 424.0245, found: 424.0256.
(Z)-5-(5-Chloro-2-((1,3-dioxoisoindolin-2-yl)methoxy)-
benzylidene)thiazolidine-2,4-dione (5i). Yellow solid; yield
72.9%; m. p. 237–239 °C; 1H NMR (d6-DMSO, 400 MHz) δ: 5.67
(s, 2H, OCH2N), 7.34 (d, 1H, J = 2.4 Hz, ArH), 7.53 (d, 1H, J =
8.8 Hz, ArH), 7.58 (dd, 1H, J = 8.8 Hz, 2.4 Hz, ArH), 7.67 (s, 1H,
CH), 7.88–7.90 (m, 2H, phthalimide), 7.91–7.94 (m, 2H,
phthalimide), 12.55 (s, 1H, NH); 13C NMR (d6-DMSO, 100 MHz)
δ: 67.6, 119.2, 124.2, 125.3, 126.3, 126.9, 127.5, 128.1, 131.6,
132.0, 135.6, 154.5, 167.1, 167.2, 167.8; HRMS (ESI) calcd for
[M − H]− C19H10ClN2O5S: 413.0004, found: 413.0010.
131.7, 132.2, 135.6, 148.4, 150.3, 167.3, 169.8, 195.9; HRMS (ESI)
calcd for [M − H]− C21H15N2O5S2: 439.0428, found: 439.0439.
(Z)-2-((3-((4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-
phenoxy)methyl)isoindoline-1,3-dione (6c). Yellow solid; yield
65.9%; m. p. 258–259 °C; 1H NMR (d6-DMSO, 400 MHz) δ:
5.64 (s, 2H, OCH2N), 7.24–7.28 (m, 2H, ArH), 7.33 (s, 1H,
ArH), 7.50 (t, 1H, J = 8.0 Hz, ArH), 7.61 (s, 1H, CH), 7.90–7.93
(m, 2H, phthalimide), 7.95–7.99 (m, 2H, phthalimide), 13.88
(s, 1H, NH); 13C NMR (d6-DMSO, 100 MHz) δ: 66.1, 118.4,
118.9, 124.2, 126.8, 131.2, 131.6, 131.7, 135.0, 135.6, 157.3,
167.4, 169.7, 196.1; HRMS (ESI) calcd for [M
C19H11N2O4S2: 395.0166, found: 395.0177.
−
H]−
(Z)-2-((2-((4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-
phenoxy)methyl)isoindoline-1,3-dione (6d). Yellow solid; yield
74.5%; m. p. 248–250 °C; 1H NMR (d6-DMSO, 400 MHz) δ:
5.69 (s, 2H, OCH2N), 7.22 (t, 1H, J = 7.2 Hz, ArH), 7.36–7.40
(m, 1H, ArH), 7.48 (d, 1H, J = 7.2 Hz, ArH), 7.55 (dt, 1H, J =
7.2 Hz, 1.6 Hz), 7.63 (s, 1H, CH), 7.88–7.91 (m, 2H,
phthalimide), 7.93–7.95 (m, 2H, phthalimide), 13.69 (s, 1H,
NH); 13C NMR (d6-DMSO, 100 MHz) δ: 67.2, 116.9, 123.8,
124.1, 124.2, 126.6, 126.9, 129.8, 131.6, 133.2, 135.6, 155.9,
(Z)-5-(2-((1,3-Dioxoisoindolin-2-yl)methoxy)-5-
nitrobenzylidene)thiazolidine-2,4-dione (5j). Yellow solid;
1
yield 64.1%; m. p. 253–254 °C; H NMR (d6-DMSO, 400 MHz)
δ: 5.86 (s, 2H, OCH2N), 7.73 (d, 1H, J = 8.8 Hz, ArH), 7.75 (s,
1H, CH), 7.91–7.93 (m, 2H, phthalimide), 7.97–7.99 (m, 2H,
phthalimide), 8.23 (d, 1H, J = 2.4 Hz, ArH), 8.38 (dd, 1H, J =
8.8 Hz, 2.4 Hz, ArH), 12.62 (s, 1H, NH); 13C NMR (d6-DMSO,
100 MHz) δ: 66.9, 115.7, 123.8, 124.1, 124.3, 124.3, 127.6,
128.0, 131.6, 135.7, 142.3, 160.0, 167.2, 167.3, 167.6; HRMS
(ESI) calcd for [M − H]− C19H10N3O7S: 424.0245, found:
424.0253.
167.3, 169.4, 196.3; HRMS (ESI) calcd for [M
C19H11N2O4S2: 395.0166, found: 395.0177.
−
H]−
(Z)-2-((4-((4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-
phenoxy)methyl)isoindoline-1,3-dione (6e). Yellow solid; yield
66.1%; m. p. 251–254 °C; 1H NMR (d6-DMSO, 400 MHz) δ:
5.67 (s, 2H, OCH2N), 7.27 (d, 2H, J = 8.8 Hz, ArH), 7.59 (d,
2H, J = 8.8 Hz, ArH), 7.63 (s, 1H, CH), 7.91–7.94 (m, 2H,
phthalimide), 7.96–7.99 (m, 2H, phthalimide), 13.78 (s, 1H,
NH); 13C NMR (d6-DMSO, 100 MHz) δ: 65.7, 117.0, 123.7,
124.2, 127.3, 131.7, 131.9, 133.0, 135.6, 158.6, 167.3, 169.9,
196.0; HRMS (ESI) calcd for [M − H]− C19H11N2O4S2: 395.0166,
found: 395.0175.
(Z)-5-(3-Chloro-4-((1,3-dioxoisoindolin-2-yl)methoxy)-
benzylidene)thiazolidine-2,4-dione (5k). Light yellow solid;
yield 68.2%; m. p. 238–239 °C; 1H NMR (d6-DMSO, 400 MHz) δ:
5.73 (s, 2H, OCH2N), 7.58 (dd, 1H, J = 8.8 Hz, 2.4 Hz, ArH), 7.62
(d, 1H, J = 8.8 Hz, ArH), 7.71 (d, 1H, J = 2.4 Hz, ArH), 7.75 (s, 1H,
CH), 7.92–7.94 (m, 2H, phthalimide), 7.98–8.00 (m, 2H,
phthalimide), 12.63 (s, 1H, NH); 13C NMR (d6-DMSO, 100 MHz)
δ: 67.0, 117.6, 123.7, 123.9, 124.3, 128.9, 130.2, 130.5, 131.6,
132.3, 135.7, 153.7, 167.2, 167.6, 168.0; HRMS (ESI) calcd for
[M − H]− C19H10ClN2O5S: 413.0004, found: 413.0001.
(Z)-2-((2-Methoxy-6-((4-oxo-2-thioxothiazolidin-5-ylidene)-
methyl)phenoxy)methyl)isoindoline-1,3-dione (6f). Yellow
1
solid; yield 77.4%; m. p. 233–235 °C; H NMR (d6-DMSO, 400
(Z)-2-((2-Methoxy-4-((4-oxo-2-thioxothiazolidin-5-ylidene)-
methyl)phenoxy)methyl)isoindoline-1,3-dione (6a). Yellow
MHz) δ: 3.88 (s, 3H, OCH3), 5.50 (s, 2H, OCH2N), 6.80–6.82
(m, 1H, ArH), 7.25–7.26 (m, 2H, ArH), 7.42 (s, 1H, CH), 7.78–
7.79 (m, 4H, phthalimide), 13.48 (s, 1H, NH); 13C NMR (d6-
DMSO, 100 MHz) δ: 56.6, 68.2, 115.9, 119.8, 123.8, 126.7,
127.1, 128.2, 129.0, 131.3, 135.4, 144.9, 153.2, 167.1, 168.5,
196.3; HRMS (ESI) calcd for [M − H]− C20H13N2O5S2: 425.0271,
found: 425.0281.
1
solid; yield 75.4%; m. p. 243–246 °C; H NMR (d6-DMSO, 400
MHz) δ: 3.77 (s, 3H, OCH3), 5.61 (s, 2H, OCH2N), 7.16 (dd,
1H, J = 8.4 Hz, 2.0 Hz, ArH), 7.22 (d, 1H, J = 2.0 Hz, ArH),
7.34 (d, 1H, J = 8.4 Hz, ArH), 7.62 (s, 1H, CH), 7.91–7.93 (m,
2H, phthalimide), 7.96–7.98 (m, 2H, phthalimide), 13.81 (s,
1H, NH); 13C NMR (d6-DMSO, 100 MHz) δ: 56.2, 66.8, 114.8,
117.7, 124.2, 124.3, 128.5, 131.7, 132.2, 135.6, 148.2, 150.7,
(Z)-2-((2,6-Dimethoxy-4-((4-oxo-2-thioxothiazolidin-5-
ylidene)methyl)phenoxy)methyl)isoindoline-1,3-dione
(6g).
167.3, 169.8, 195.9; HRMS (ESI) calcd for [M
C20H13N2O5S2: 425.0271, found: 425.0275.
−
H]−
Yellow solid; yield 80.4%; m. p. 241–243 °C; 1H NMR (d6-
DMSO, 400 MHz) δ: 3.59 (s, 6H, OCH3), 5.45 (s, 2H, OCH2N),
6.82 (s, 2H, ArH), 7.58 (s, 1H, CH), 7.89–7.94 (m, 4H,
phthalimide), 13.85 (s, 1H, NH); 13C NMR (d6-DMSO, 100
MHz) δ: 56.4, 68.1, 108.0, 124.0, 125.5, 130.3, 131.7, 132.2,
135.4, 136.8, 154.1, 167.4, 169.7, 195.9; HRMS (ESI) calcd for
[M − H]− C21H15N2O6S2: 455.0377, found: 455.0386.
(Z)-2-((2-Ethoxy-4-((4-oxo-2-thioxothiazolidin-5-ylidene)-
methyl)phenoxy)methyl)isoindoline-1,3-dione (6b). Yellow
1
solid; yield 83.6%; m. p. 264–267 °C; H NMR (d6-DMSO, 400
MHz) δ: 1.25 (t, 3H, J = 6.8 Hz, OCH CH_ ), 4.00 (q, 2H, J = 6.8
_
2
3_
Hz, OCH_ CH ), 5.61 (s, 2H, OCH N), 7.14 (dd, 1H, J = 8.4 Hz, 2.0
_
2_
3
2
Hz, ArH), 7.20 (d, 1H, J = 2.0 Hz, ArH), 7.32 (d, 1H, J = 8.4 Hz,
ArH), 7.61 (s, 1H, CH), 7.90–7.93 (m, 2H, phthalimide), 7.94–7.97
(m, 2H, phthalimide), 13.81 (s, 1H, NH); 13C NMR (d6-DMSO,
100 MHz) δ: 14.8, 64.6, 67.2, 115.9, 119.1, 124.2, 124.3, 128.9,
(Z)-2-((2-Nitro-4-((4-oxo-2-thioxothiazolidin-5-ylidene)-
methyl)phenoxy)methyl)isoindoline-1,3-dione (6h). Yellow
1
solid; yield 58.1%; m. p. 237–239 °C; H NMR (d6-DMSO, 400
MHz) δ: 5.83 (s, 2H, OCH2N), 7.67 (s, 1H, CH), 7.85 (d, 1H, J
Med. Chem. Commun.
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