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(E)-1-(3,4,5-Trimethoxyphenyl)-3-(2,3,6-tris(4-methoxyphenyl)-
imidazo[2,1-b]thiazol-5 yl)prop-2-en-1-one (11m): Yellow solid
(171 mg, 81%); mp: 194–1998C; FT-IR: n˜ =2926, 1651, 1586, 1124,
834; 1H NMR (300 MHz, CDCl3): d=7.64 (d, J=8.68 Hz, 2H), 7.42–
7.25 (m, 3H), 7.18–7.05 (m, 3H), 7.02–6.94 (m, 2H), 6.83 (s, 2H),
6.81–6.60 (m, 4H), 3.93–3.71 ppm (m, 18H); 13C NMR (75 MHz,
CDCl3): d=187.55, 160.79, 159.68, 159.51, 152.70, 150.40, 150.34,
141.67, 133.38, 131.95, 130.41, 130.30, 129.77, 129.43, 128.47,
128.32, 127.51, 123.52, 121.66, 120.64, 118.69, 114.79, 114.03,
105.34, 60.77, 56.08, 55.15 ppm; MS (ESI): m/z 663 [M+H]+; HRMS
(ESI): m/z [M+H]+ calcd for C38H35N2O7S: 663.2159, found:
663.2162.
160.90, 159.62, 152.77, 150.43, 148.62, 141.91, 134.26, 133.67,
133.18, 132.68, 132.02, 130.44, 130.12, 129.34, 128.84, 128.26,
127.88, 127.27, 123.40, 119.74, 114.88, 114.12, 105.24, 60.83, 56.11,
55.21 ppm; MS (ESI): m/z 667 [M+H]+; HRMS (ESI): m/z [M+H]+
calcd for C37H32ClN2O6S: 667.1664, found: 667.1667.
(E)-3-(6-(4-Chlorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-
b]thiazol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
Yellow solid (142 mg, 71%); mp: 211–2138C; FT-IR: n˜ =1652, 1584,
1205, 1026, 838, 695 cmÀ1 1H NMR (300 MHz, CDCl3): d=7.67 (d,
(11r):
;
J=8.30 Hz, 2H), 7.44 (d, J=8.30 Hz, 2H), 7.36–7.28 (m, 4H), 7.14 (d,
J=9.06 Hz, 2H), 6.95 (d, J=8.30 Hz, 2H), 6.81–6.72 (m, 4H), 6.52 (d,
J=15.10 Hz, 1H), 3.93 (s, 3H), 3.88 (s, 3H), 3.79 (s, 3H), 3.76 ppm
(s, 3H); 13C NMR (125 MHz, CDCl3): d=187.21, 160.86, 159.63,
152.83, 150.55, 148.88, 148.86, 134.24, 133.43, 132.19, 130.98,
130.38, 130.24, 128.95, 128.87, 128.37, 127.13, 123.55, 122.51,
122.04, 120.76, 120.66, 114.79, 114.14, 110.38, 109.74, 56.01, 55.89,
55.30, 55.25 ppm; MS (ESI): m/z 637 [M+H]+.
(E)-1-(3,4-Dimethoxyphenyl)-3-(2,3,6-tris(4-methoxyphenyl)-
imidazo[2,1-b]thiazol-5-yl)prop-2-en-1-one (11n): Yellow solid
(149 mg, 74%); mp: 190–1948C; FT-IR: n˜ =2354, 1650, 1597, 1252,
1
1023 cmÀ1; H NMR (300 MHz, CDCl3): d=7.66 (d, J=8.68 Hz, 2H),
7.46 (d, J=15.67 Hz, 1H), 7.34 (d, J=8.68 Hz, 2H), 7.30 (d, J=
1.7 Hz, 1H), 7.13 (d, J=8.87 Hz, 2H), 7.03–6.91 (m, 5H), 6.81–6.2
(m, 3H), 6.51 (d, J=15.67 Hz, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 3.86 (s,
3H), 3.77 (s, 3H), 3.75 ppm (s, 3H); 13C NMR (125 MHz, CDCl3): d=
187.44, 160.76, 159.72, 159.52, 152.63, 150.65, 150.54, 148.74,
132.16, 131.19, 130.39, 130.22, 129.42, 128.47, 127.33, 126.62,
123.68, 122.43, 121.62, 120.95, 119.51, 114.70, 114.06, 110.45,
109.65, 55.95, 55.85, 55.26, 55.21 ppm; MS (ESI): m/z 633 [M+H]+;
HRMS (ESI): m/z [M+H]+ calcd for C37H33N2O6S: 633.2053, found:
633.2059.
(E)-3-(6-(4-Chlorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-
b]thiazol-5-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one
Yellow solid (161 mg, 79%); mp: 206–2108C; FT-IR: n˜ =1654, 1575,
1249, 1027, 827, 702 cmÀ1 1H NMR (500 MHz, CDCl3): d=7.65 (d,
(11s):
;
J=8.39 Hz, 2H), 7.57 (d, J=1.83 Hz, 1H), 7.46 (d, J=8.26 Hz, 2H),
7.43 (t, J=3.81 Hz, 2H), 7.34 (d, J=1.83 Hz, 1H), 7.32 (d, J=
8.54 Hz, 2H), 7.13 (d, J=8.85 Hz, 2H), 6.92 (d, J=8.69 Hz, 2H), 6.80
(d, J=8.69 Hz, 2H), 6.21 (d, J=15.56 Hz, 1H), 3.79 (s, 3H),
3.73 ppm (s, 3H); 13C NMR (125 MHz, CDCl3): d=186.85, 160.85,
159.74, 151.52, 150.66, 137.58, 136.67, 134.71, 132.98, 132.77,
132.19, 130.62, 130.40, 130.31, 130.05, 129.02, 128.42, 127.52,
127.07, 123.34, 121.74, 120.79, 119.52, 114.72, 114.19, 55.28 ppm;
MS (ESI): m/z 645 [M+H]+; HRMS (ESI): m/z [M+H]+ calcd for
C34H24Cl3N2O3S: 645.0567, found: 645.0575.
(E)-1-(3,4-Dichlorophenyl)-3-(2,3,6-tris(4-methoxyphenyl)imidazo-
[2,1-b]thiazol-5-yl)prop-2-en-1-one (11o): Yellow solid (157 mg,
77%); mp: 188–1938C; FT-IR: n˜ =1658, 1575, 1255, 1029, 831 cmÀ1
;
1H NMR (300 MHz, CDCl3): d=7.64 (d, J=8.68 Hz, 2H), 7.57 (d, J=
1.7 Hz, 1H), 7.50 (d, J=15.67 Hz, 1H), 7.42 (d, J=8.30 Hz, 1H), 7.36
(d, J=1.88 Hz, 1H), 7.33 (d, J=8.68 Hz, 2H), 7.13 (d, J=8.87 Hz,
2H), 7.02 (d, J=8.68 Hz, 2H), 6.92 (d, J=8.68 Hz, 2H), 6.79 (d, J=
8.68 Hz, 2H), 6.23 (d, J=15.48 Hz, 1H), 3.88 (s, 3H), 3.78 (s, 3H),
3.73 ppm (s, 3H); 13C NMR (75 MHz, CDCl3): d=187.00, 160.84,
160.09, 152.46, 137.89, 136.46, 132.22, 131.20, 130.53, 130.33,
130.07, 128.58, 127.15, 127.07, 126.95, 123.52, 121.48, 121.02,
118.31, 114.73, 114.27, 114.18, 55.39, 55.30 ppm; MS (ESI): m/z
641[M+H]+; HRMS (ESI): m/z [M+H]+ calcd for C35H27Cl2N2O4S:
641.1063, found: 641.1070.
(E)-3-(6-(4-Chlorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-
b]thiazol-5-yl)-1-(pyridin-2-yl)prop-2-en-1-one (11t): Yellow solid
(107 mg, 59%); mp: 192–1958C; FT-IR: n˜ =1660, 1574, 1252, 1026,
836, 671 cmÀ1
;
1H NMR (300 MHz, CDCl3): d=8.52 (d, J=
3.77 Hz,1H), 7.93 (d, J=8.30 Hz,1H), 7.76 (dt, J=7.55, 1.51 Hz,1H),
7.68 (d, J=8.30 Hz, 2H), 7.49 (d, J=15.86 Hz,1H), 7.43–7.29 (m,
5H), 7.17–7.07 (m, 3H), 6.89 (d, J=8.30 Hz, 2H), 6.78 (d, J=8.30 Hz,
2H), 3.77 (s, 3H), 3.70 ppm (s, 3H); 13C NMR (125 MHz, CDCl3): d=
188.73, 160.70, 159.59, 154.10, 150.78, 149.45, 148.56, 136.55,
134.16, 133.14, 132.16, 130.29, 130.23, 129.71, 128.78, 128.59,
126.94, 126.25, 123.59, 122.40, 122.31, 120.82, 114.66, 114.09, 55.23,
55.20 ppm; MS (ESI): m/z 578 [M+H]+; HRMS (ESI): m/z [M+H]+
calcd for C33H25ClN3O3S: 578.1299, found: 578.1314.
(E)-1-(Pyridin-2-yl)-3-(2,3,6-tris(4-methoxyphenyl)imidazo[2,1-
b]thiazol-5-yl)prop-2-en-1-one (11p): Yellow solid (102 mg, 56%);
mp: 191–1948C; FT-IR: n˜ =2832, 1655, 1570, 1251, 1024, 617 cmÀ1
;
1H NMR (500 MHz, CDCl3): d=8.50 (d, J=4.27 Hz, 1H), 7.91 (d, J=
7.78 Hz, 1H), 7.74 (t, J=7.62 Hz, 1H), 7.68 (d, J=8.69 Hz, 2H), 7.59
(d, J=16.02 Hz, 1H), 7.32 (d, J=8.54 Hz, 2H), 7.19–7.09 (m, 3H),
7.02–6.96 (m, 3H), 6.87 (d, J=8.54 Hz, 2H), 6.78 (d, J=8.39 Hz, 2H),
3.86–3.66 ppm (m, 9H); 13C NMR (125 MHz, CDCl3): d=188.89,
160.58, 159.73, 159.48, 154.33, 151.41, 150.95, 148.44, 136.44,
132.15, 130.35, 130.32, 130.25, 128.76, 127.04, 126.41, 126.02,
123.73, 122.33, 121.89, 121.01, 119.76, 114.54, 114.03, 114.01, 55.26,
55.20, 55.12 ppm; MS (ESI): m/z 574 [M+H]+; HRMS (ESI): m/z [M+
H]+ calcd for C34H28N3O4S: 574.1795, found: 574.1777.
(E)-3-(6-(4-Fluorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-
b]thiazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (11u):
Yellow solid (166 mg, 78%); mp: 214–2178C; FT-IR: n˜ =2980, 2868,
1
1650, 1570, 1257, 829, 615 cmÀ1; H NMR (400 MHz, CDCl3): d=7.71
(dd, J=9.26, 5.89 Hz, 2H), 7.40–7.34 (m, 2H), 7.21–7.14 (m, 4H),
6.98 (d, J=8.41 Hz, 2H), 6.84–6.71 (m, 5H), 6.59J=15.15 Hz, 1H),
3.91–3.73 ppm (m, 15H); 13C NMR (75 MHz, CDCl3): d=187.35,
161.02, 160.85, 159.59, 152.73, 150.34, 149.068, 141.85, 133.18,
132.66, 131.99, 130.91, 130.12, 129.43, 128.26, 127.10, 121.86,
120.49, 119.45, 115.78, 115.49, 114.82, 114.07, 105.34, 60.80, 56.06,
55.15 ppm; MS (ESI): m/z 651 [M+H]+; HRMS (ESI): m/z [M+H]+
calcd for C37H32FN2O6S: 651.1959, found: 651.1964.
(E)-3-(6-(4-Chlorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-
b]thiazol-5-yl)-1-(3,4,5 trimethoxyphenyl)prop-2-en-1-one (11q):
Yellow solid (160 mg, 76%); mp: 214–2198C; FT-IR: n˜ =2935, 2833,
1
1650, 1568, 1260, 827 cmÀ1; H NMR (500 MHz, CDCl3): d=7.67 (d,
(E)-1-(3,4-Dimethoxyphenyl)-3-(6-(4-fluorophenyl)-2,3-bis(4
methoxyphenyl)imidazo[2,1-b]thiazol-5-yl)prop-2-en-1-one
(11v): Yellow solid (152 mg, 75%); mp: 207–2118C; FT-IR: n˜ =2933,
J=8.39 Hz, 2H), 7.44 (d, J=8.39 Hz, 2H), 7.37–7.32 (m, 3H), 7.15 (d,
J=8.69 Hz, 2H), 6.97 (d, J=8.69 Hz, 2H), 6.83 (s, 2H), 6.79 (d, J=
8.69 Hz, 2H), 6.65 (d, J=15.56 Hz, 1H), 3.88 (s, 3H), 3.82 (s, 6H),
3.80 (s, 3H), 3.78 ppm (s, 3H); 13C NMR (75 MHz, CDCl3): d=187.26,
1
2834, 1644, 1593, 1268, 1023, 617 cmÀ1; H NMR (300 MHz, CDCl3):
d=7.70 (dd, J=8.30, 5.28 Hz, 2H), 7.41 (d, J=15.86 Hz, 1H), 7.34
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