Y.K. Abhale et al.
Bioorganic Chemistry 115 (2021) 105192
Thiazolidinone C-5H), 3.76 (d, J = 15.4 Hz, 1H, Thiazolidinone C-5H),
(m, 7H, Ar-H), 6.97 (s, 1H, Thiazole-H), 6.10 (s, 1H, Thiazolidinone C-
2H), 4.22 (dd, J = 15.4, 0.6 Hz, 1H, Thiazolidinone C-5H), 3.77 (d, J =
15.5 Hz, 1H, Thiazolidinone C-5H), 2.40 (s, 3H, Ar-CH3); 13C NMR (100
13
–
2.28 (s, 3H, Ar-CH3); C NMR (100 MHz, CDCl ) δ 171.6 (C O,
–
Thiazolidinone C-4), 169.0 (C, Thiazole C-2), 155.53(C, Thiazole C-4),
136.5, 134.22, 133.5, 131.42, 129.8, 129.3, 128.5, 125.6, 115.8 (CH,
Thiazole C-5), 61.5 (CH, Thiazolidinone C-2), 33.1 (CH2, Thiazolidinone
C-5), 21.4 (CH3, Ar-CH3); HRMS (m/z): calculated for (M + H)+,
–
MHz, CDCl ) δ 171.4 (C O, Thiazolidinone C-4), 169.7 (C, Thiazole C-
–
3
2), 155.8 (C, Thiazole C-4), 140.7, 137.7, 130.4, 129.5, 129.2, 127.2,
126.5, 125.5, 114.7 (CH, Thiazole C-5), 61.7 (CH, Thiazolidinone C-2),
33.2 (CH2, Thiazolidinone C-5), 21.4 (CH3, Ar-CH3); HRMS (m/z):
calculated for (M + H)+, C19H17N2OS2, 353.0782, Found: 353.0788 (M
+ H) + .
C
19H16ClN2OS2, 387.0393, Found: 387.0396 (M + H)+, 389.0369 (M +
H + 2) + .
4.2.3.9. 2-(2-(4-Chlorophenyl)thiazol-4-yl)-3-(4-(trifluoromethyl)phenyl)
thiazolidin-4-one (5i). Yield: 72 %; mp 104–105 ◦C. IR (KBr): 1356,
1512, 1604, 1681 cmꢀ 1; 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J = 8.6
Hz, 2H, Ar-H), 7.58 (d, J = 8.6 Hz, 2H, Ar-H), 7.46 (d, J = 8.5 Hz, 2H, Ar-
H), 7.41 (d, J = 8.6 Hz, 2H, Ar-H), 7.07 (s, 1H, Thiazole-H), 6.19 (d, J =
0.7 Hz, 1H, Thiazolidinone C-2H), 4.19 (dd, J = 15.7, 1.0 Hz, 1H,
Thiazolidinone C-5H), 3.79 (d, J = 15.7 Hz, 1H, Thiazolidinone C-5H);
4.2.3.14. 3-(4-Chlorophenyl)-2-(2-p-tolylthiazol-4-yl)thiazolidin-4-one
(5n). Yield: 70 %; mp 100–102 ◦C. IR (KBr): 1356, 1512, 1604, 1684
cmꢀ 1; 1H NMR (500 MHz, CDCl3) δ 7.81 (d, J = 8.2 Hz, 2H, Ar-H), 7.27
(d, J = 8.9 Hz, 2H, Ar-H), 7.24 (d, J = 8.0 Hz, 2H, Ar-H), 7.20 (d, J = 8.9
Hz, 2H, Ar-H), 6.97 (s, 1H, Thiazole-H), 6.05 (d, J = 1.0 Hz, 1H, Thia-
zolidinone C-2H), 4.20 (dd, J = 15.5, 1.2 Hz, 1H, Thiazolidinone C-5H),
13
–
C NMR (100 MHz, CDCl ) δ 171.4 (C O, Thiazolidinone C-4), 168.8
3.76 (d, J = 15.5 Hz, 1H, Thiazolidinone C-5H), 2.40 (s, 3H, Ar-CH3);
–
3
13
–
(C, Thiazole C-2), 155.4 (C, Thiazole C-4), 139.6, 134.21, 132.0, 129.7,
128.9, 127.9, 126.5, 125.8, 117.6, 115.8 (CH, Thiazole C-5), 61.4 (CH,
Thiazolidinone C-2), 33.0 (CH2, Thiazolidinone C-5); HRMS (m/z):
calculated for (M + H)+, C19H13ClF3N2OS2, 441.0110, Found: 441.0114
(M + H)+, 443.0085 (M + H + 2) + .
C NMR (100 MHz, CDCl ) δ 171.4 (C O, Thiazolidinone C-4), 170.0
–
3
(C, Thiazole C-2), 155.5 (C, Thiazole C-4), 140.1, 136.3, 132.8, 130.4,
129.6, 129.4, 126.8, 126.5, 114.9 (CH, Thiazole C-5), 61.5 (CH, Thia-
zolidinone C-2), 33.1 (CH2, Thiazolidinone C-5), 21.4 (CH3, Ar-CH3);
HRMS (m/z): calculated for (M + H)+, C19H16ClN2OS2, 387.0393,
Found: 387.0388 (M + H)+, 389.0366 (M + H + 2)+.
4.2.3.10. 3-(4-Chlorophenyl)-2-(2-(4-fluorophenyl)thiazol-4-yl)thiazoli-
din-4-one (5j). Yield: 70 %; mp 109–110 ◦C. IR (KBr): 1356, 1512, 1604,
1682 cmꢀ 1; 1H NMR (400 MHz, CDCl3) δ 7.90 (dd, J = 8.9, 5.2 Hz, 2H,
Ar-H), 7.28 (d, J = 8.9 Hz, 2H, Ar-H), 7.20 (d, J = 8.9 Hz, 2H, Ar-H),
7.13 (t, J = 8.6 Hz, 2H, Ar-H), 7.01 (s, 1H, Thiazole-H), 6.07 (d, J =
1.0 Hz, 1H, Thiazolidinone C-2H), 4.19 (dd, J = 15.5, 1.1 Hz, 1H,
Thiazolidinone C-5H), 3.77 (d, J = 15.5 Hz, 1H, Thiazolidinone C-5H);
(C, Thiazole C-2), 165.4, 1362.9, 155.8 (C, Thiazole C-4), 136.8, 132.41,
129.4, 129.3, 128.6, 128.6, 127.0, 120.9, 116.3, 116.1, 115.4 (CH,
Thiazole C-5), 61.4 (CH, Thiazolidinone C-2), 33.2 (CH2, Thiazolidinone
C-5); HRMS (m/z): calculated for (M + H)+, C18H13ClFN2OS2, 391.0142,
Found: 391.0139 (M + H)+, 393.0110 (M + H + 2) + .
4.2.3.15. 3-(4-Fluorophenyl)-2-(2-p-tolylthiazol-4-yl)thiazolidin-4-one
(5o). Yield: 64 %; mp 128–129 ◦C. IR (KBr): 1356, 1512, 1604, 1682
cmꢀ 1; 1H NMR (500 MHz, CDCl3) δ 7.81 (d, J = 8.2 Hz, 2H, Ar-H), 7.24
(d, J = 8.0 Hz, 2H, Ar-H), 7.19 (dd, J = 9.0, 4.9 Hz, 2H, Ar-H), 7.01 –
6.97 (m, 2H, Ar-H), 6.96 (s, 1H, Thiazole-H), 6.00 (d, J = 1.1 Hz, 1H,
Thiazolidinone C-2H), 4.22 (dd, J = 15.5, 1.2 Hz, 1H, Thiazolidinone C-
5H), 3.76 (d, J = 15.5 Hz, 1H, Thiazolidinone C-5H), 2.39 (s, 3H, Ar-
13
–
C NMR (100 MHz, CDCl ) δ 171.4 (C O, Thiazolidinone C-4), 168.7
–
CH3); 13C NMR (100 MHz, CDCl ) δ 171.6 (C O, Thiazolidinone C-4),
–
–
3
169.9 (C, Thiazole C-2), 162.3, 160.3, 155.5 (C, Thiazole C-4), 140.9,
133.6, 130.4, 129.6, 127.9, 127.8, 126.5, 116.3, 116.1, 115.0 (CH,
Thiazole C-5), 61.8 (CH, Thiazolidinone C-2), 33.0 (CH2, Thiazolidinone
C-5), 21.4 (CH3, Ar-CH3); HRMS (m/z): calculated for (M + H)+,
C19H16FN2OS2, 371.0688, Found: 371.0688 (M + H) + .
4.2.3.11. 3-(4-Fluorophenyl)-2-(2-(4-fluorophenyl)thiazol-4-yl)thiazoli-
din-4-one (5 k). Yield: 60 %; mp 105–107 ◦C. IR (KBr): 1356, 1512,
1604, 1680 cmꢀ 1; 1H NMR (400 MHz, CDCl3) δ 7.88–7.92 (m, 2H, Ar-H),
6.92–7.12 (m, 7H, Ar-H, Thiazole-H), 6.07 (d, J = 1.0 Hz, 1H, Thiazo-
lidinone C-2H), 4.20 (dd, J = 15.5 and 1.0 Hz, 1H, Thiazolidinone C-
4.2.3.16. 3-p-Tolyl-2-(2-p-tolylthiazol-4-yl)thiazolidin-4-one (5p). Yield:
66 %; mp 141–143 ◦C. IR (KBr): 1356, 1512, 1604, 1682 cmꢀ 1; 1H NMR
(500 MHz, CDCl3) δ 7.82 (d, J = 8.2 Hz, 2H, Ar-H), 7.23 (d, J = 7.9 Hz,
2H, Ar-H), 7.11 (s, 4H, Ar-H), 6.95 (s, 1H, Thiazole-H), 6.04 (d, J = 1.3
Hz, Thiazolidinone C-2H), 4.21 (dd, J = 15.4, 1.3 Hz, 1H, Thiazolidi-
none C-5H), 3.76 (d, J = 15.4 Hz, 1H, Thiazolidinone C-5H), 2.39 (s, 3H,
Ar-CH3), 2.28 (s, 3H, Ar-CH3); 13C NMR (100 MHz, CDCl3) δ 171.4
5H), 3.78 (d, J = 15.5 Hz, 1H, Thiazolidinone C-5H); 13C NMR (100
–
MHz, CDCl ) δ 171.5 (C O, Thiazolidinone C-4), 169.1 (C, Thiazole C-
–
3
2), 161.4, 159.8, 155.5 (C, Thiazole C-4), 136.5, 129.3, 128.8, 125.9,
116.4, 116.2, 115.8 (CH, Thiazole C-5), 61.5 (CH, Thiazolidinone C-2),
33.3 (CH2, Thiazolidinone C-5); HRMS (m/z): calculated for (M + H)+,
C18H13F2N2OS2, 375.0437, Found: 375.0440 (M + H) + .
–
(C O, Thiazolidinone C-4), 169.7 (C, Thiazole C-2), 156.0 (C, Thiazole
–
C-4), 140.8, 137.3, 135.1, 130.5, 129.8, 129.6, 126.5, 125.6, 114.7 (CH,
Thiazole C-5), 61.8 (CH, Thiazolidinone C-2), 33.1 (CH2, Thiazolidinone
C-5), 21.4 (CH3, Ar-CH3), 21.0 (CH3, Ar-CH3); HRMS (m/z): calculated
for (M + H)+, C20H19N2OS2, 367.0939, Found: 367.0941 (M + H) + .
4.2.3.12. 2-(2-(4-Fluorophenyl)thiazol-4-yl)-3-p-tolylthiazolidin-4-one (5
l). Yield: 72 %; mp 139–141 ◦C. IR (KBr): 1356, 1512, 1604, 1681 cmꢀ 1
;
1H NMR (400 MHz, CDCl3) δ 7.91 (dd, J = 8.7, 5.3 Hz, 2H, Ar-H), 7.18 –
7.06 (m, 6H, Ar-H), 6.99 (s, 1H, Thiazole-H), 6.06 (s, 1H, Thiazolidinone
C-2H), 4.19 (d, J = 15.4 Hz, 1H, Thiazolidinone C-5H), 3.76 (d, J = 15.4
4.2.3.17. 3-(4-(Trifluoromethyl)phenyl)-2-(2-p-tolylthiazol-4-yl)thiazoli-
din-4-one (5q). Yield: 60 %; mp 120–122 ◦C. IR (KBr): 1356, 1512,
1604, 1680 cmꢀ 1; 1H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.6 Hz, 2H,
Ar-H), 7.55 (d, J = 8.6 Hz, 2H, Ar-H), 7.08–7.20 (m, 4H, Ar-H), 7.01 (s,
1H, Thiazole-H), 6.10 (d, J = 1.0 Hz, 1H, Thiazolidinone C-2H), 4.20
(dd, J = 15.5 and 1.0 Hz, 1H, Thiazolidinone C-5H), 3.77 (d, J = 15.7
Hz, 1H, Thiazolidinone C-5H), 2.44 (s, 3H, Ar-CH3); 13C NMR (100 MHz
Hz, 1H, Thiazolidinone C-5H), 2.28 (s, 3H, Ar-CH3). 13C NMR (100 MHz,
–
CDCl ) δ 171.5 (C O, Thiazolidinone C-4), 168.4 (C, Thiazole C-2),
–
3
165.4, 162.9, 156.2 (C, Thiazole C-4), 137.4, 135.0, 130.0, 129.5, 129.5,
128.6, 128.6, 125.7, 116.2, 116.0, 115.3 (CH, Thiazole C-5), 61.8 (CH,
Thiazolidinone C-2), 33.2 (CH2, Thiazolidinone C-5), 21.1 (CH3, Ar-
CH3); HRMS (m/z): calculated for (M + H)+, C19H16FN2OS2, 371.0688,
Found: 371.0690 (M + H) + .
–
CDCl ) δ 171.6 (C O, Thiazolidinone C-4), 169.7 (C, Thiazole C-2),
–
3
155.2 (C, Thiazole C-4), 137.8, 134.20, 132.5, 131.1, 129.8, 128.0,
127.1, 125.8, 124.8, 115.9 (CH, Thiazole C-5), 61.4 (CH, Thiazolidinone
C-2), 33.0 (CH2, Thiazolidinone C-5), 21.3 (CH3, Ar-CH3); HRMS (m/z):
calculated for (M + H)+, C20H16F3N2OS2, 421.0656, Found: 421.0660
(M + H) + .
4.2.3.13. 3-Phenyl-2-(2-p-tolylthiazol-4-yl)thiazolidin-4-one (5 m).
Yield: 68 %; mp: 118–120 ◦C. IR (KBr): 1356, 1512, 1604, 1684 cmꢀ 1
;
1H NMR (500 MHz, CDCl3) δ 7.82 (d, J = 8.1 Hz, 2H, Ar-H), 7.33–7.27
6