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1 : 1); anal. calcd: C 62.41, H 4.45, N 7.28, S 8.33; found: C 62.22, column chromatography; yellow powder, mp 198–200 C; yield
H 4.58, N 7.10, S 8.51%.
22%; 1H-NMR (300 MHz; DMSO-d6) d: 2.18–2.22 (m, 2H,
(Z)-2-(3-(2-Chlorobenzyloxy)benzylidene)-6,7-dihydro-2H-imidazo- SCH2CH2), 3.25 (def.t, J ¼ 5.50 Hz, 2H, SCH2), 3.66 (t, J ¼ 5.77 Hz,
[2,1-b][1,3]thiazin-3(5H)-one (33). Product 33 was puried by 2H, NCH2), 6.91 (s, 1H, ArCH]), 7.39 (dd, J ¼ 8.80 Hz, J ¼ 1.93
crystallization; yellow powder, mp 171–173 ꢄC (twice crystalli- Hz, 2H, Ar H-30, H-50), 7.63 (t, J ¼ 7.56 Hz, 2H, Ar H-300, H-500), 7.79
zation, acetonitrile); yield 14.38%; 1H-NMR (300 MHz; CDCl3) d: (t, J ¼ 6.05 Hz, 1H, Ar H-400), 8.16 (dd, J ¼ 6.88 Hz, J ¼ 1.65 Hz, 2H,
2.23–2.30 (m, 2H, SCH2CH2), 3.13 (def.t, J ¼ 5.64 Hz, 2H, SCH2), Ar H-200, H-600), 8.27 (dd, J ¼ 8.80 Hz, J ¼ 2.48 Hz, Ar H-20, H-60);
3.73 (t, J ¼ 5.77 Hz, 2H, NCH2), 5.22 (s, 2H, CH2O), 6.92 (s, 1H, 13C-NMR (75 MHz; CDCl3) d: 22.86 (CH2); 26.15 (SCH2); 39.87
ArCH]), 6.98 (dd, J ¼ 8.25 Hz, J ¼ 0.77 Hz, 1H, Ar H-40), 7.24– (NCH2); 122.02; 123.07; 128.61; 129.93; 130.22; 132.04; 133.20;
7.37 (m, 3H, Ar H-300, Ar H-400, H-600), 7.41 (m, 1H, Ar H-50), 7.56– 133.72; 137.19; 151.97 (ArCH]C); 160.25 (C]O); 164.84 (C]O);
7.59 (m, 1H, Ar H-600); 7.64 (d, J ¼ 7.69 Hz, 1H, Ar H-60), 7.86 (t, J 168.88 (C]N); IR n: 1736 (COO), 1713 (C]O), 1634 (ArCH]),
¼ 8.05 Hz, 1H, Ar H-20); 13C-NMR (75 MHz; CDCl3) d: 22.93 1593 (C]N), 1486, 1469, 1248, 1200, 1170, 1066, 1024, 899, 712;
(CH2); 26.12 (SCH2); 39.86 (NCH2); 67.21 (CH2O); 116.97; 117.36; Rf ¼ 0.55; tR ¼ 7.25; purity 99.25%; MS calcd for [M + H]+:
123.92; 125.22; 126.94; 128.94; 128.99; 129.41; 129.63; 132.71; C20H16N2O3S m/z: 364.4, found 365.2; CC (CH2Cl2 : AcOEt 1 : 1);
134.62; 135.58; 137.61; 158.52 (ArCH]C); 160.09 (C]O); 168.96 anal. calcd: C 65.91, H 4.43, N 7.69, S 8.80; found: C 65.61, H 4.68,
(C]N); IR n: 1714 (C]O), 1632 (ArCH]), 1578 (C]N), 1484, N 7.45, S 8.49%.
1437, 1360, 1288, 1263, 1155, 1017, 759; Rf ¼ 0.62; tR ¼ 8.09;
(Z)-4-((3-Oxo-6,7-dihydro-3H-imidazo[2,1-b][1,3]thiazin-2(5H)-
purity 99.13%; MS calcd for [M + H]+: C20H17N2O2ClS m/z: ylidene)metyl)phenyl 4-chloro-benzoate (37). Product 37 was
384.88, found 385.27; anal. calcd: C 62.41, H 4.45, N 7.28, S 8.33; puried by column chromatography; yellow powder, mp 212–214
found: C 62.36, H 4.98, N 7.37, S 8.40%.
ꢄC; yield 27%; 1H-NMR (300 MHz; DMSO-d6) d: 2.19–2.21 (m, 2H,
(Z)-2-(3-(2,4-Dichlorobenzyloxy)benzylidene)-6,7-dihydro-2H- SCH2CH2), 3.22–3.30 (m, 2H, SCH2), 3.66 (t, J ¼ 5.64 Hz, 2H,
imidazo[2,1-b][1,3]thiazin-3(5H)-one (34). Product 34 was puri- NCH2), 6.90 (s, 1H, ArCH]), 7.39 (d, J ¼ 8.80 Hz, J ¼ 1.92 Hz, 2H,
ed by column chromatography; yellow powder, mp 160–162 ꢄC; Ar H-30, H-50), 7.70 (d, J ¼ 8.50 Hz, J ¼ 1.92 Hz, 2H, Ar H-300, H-500),
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yield 13%; H-NMR (300 MHz) d: 2.15 (def.t, J ¼ 2.43 Hz, 2H, 8.16 (d, J ¼ 8.52 Hz, J ¼ 1.92 Hz, 2H, Ar H-200, H-600), 8.26 (d, J ¼
SCH2CH2), 3.21 (def.t, J ¼ 5.51 Hz, 2H, SCH2), 3.60 (t, J ¼ 5.64 8.80 Hz, J ¼ 1.92 Hz, 2H, Ar H-20, H-60); 13C-NMR (75 MHz; CDCl3)
Hz, 2H, NCH2), 5.15 (s, 2H, CH2O), 6.78 (s, 1H, ArCH]), 7.03 d: 22.86 (CH2); 26.15 (SCH2); 39.86 (NCH2); 121.91; 122.96;
(dd, J ¼ 7.71 Hz, J ¼ 2.30 Hz, 1H, Ar H-40), 7.34 (t, J ¼ 8.08 Hz, 127.78; 128.98; 131.58; 132.16; 133.20; 137.17; 140.26; 151.72
1H, Ar H-50), 7.43 (d, J ¼ 2.05 Hz, 1H, Ar H-500), 7.47 (d, J ¼ 2.31 (ArCH]C); 160.39 (C]O); 163.98 (C]O); 168.81 (C]N); IR n:
Hz, 1H, Ar H-300), 7.58–7.69 (m, 2H, Ar H-600, H-60), 7.88 (s, 1H, Ar 1741 (COO), 1714 (C]O), 1635 (ArCH]), 1591 (C]N), 1482,
H-20); 13C-NMR (75 MHz; CDCl3) d: 22.92 (CH2); 26.12 (SCH2); 1358, 1259, 1199, 1163, 1067, 1013, 751; Rf ¼ 0.59; tR ¼ 7.99;
39.85 (NCH2); 66.66 (CH2O); 116.98; 117.13; 123.68; 125.42; purity 98.96%; MS calcd for [M + H]+: C20H15N2O3SCl m/z: 398.9,
127.27; 129.22; 129.65; 129.76; 133.27; 133.33; 134.05; 135.66; found 399.2; CC (CH2Cl2 : AcOEt 1 : 1); anal. calcd: C 60.22, H
137.72; 158.26 (ArCH]C); 160.20 (C]O); 168.93 (C]N); IR n: 3.79, N 7.02, S 8.04; found: C 60.08, H 4.09, N 6.93, S 8.49%.
1709 (C]O), 1634 (ArCH]), 1572 (C]N), 1486, 1443, 1294,
(Z)-2-(3-(Benzyloxy)benzylidene)-5,6,7,8-tetrahydroimidazo[2,1-
1258, 1161, 1045, 907, 779; Rf ¼ 0.51; tR ¼ 8.81; purity 98.11%; b][1,3]thiazepin-3(2H)-one (42). Product 42 was puried by
MS calcd for [M + H]+: C20H18N2O2Cl2S m/z: 419.3, found 419.1; column chromatography; yellow powder, mp 139–141 ꢄC
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CC (CH2Cl2 : AcOEt 1 : 1); anal. calcd: C 57.28, H 3.84, N 6.68, S (acetonitrile, dioxane); yield 29%; H-NMR (300 MHz; DMSO-
7.65; found: C 57.03, H 4.18, N 6.64, S 7.73%.
d6) d: 1.78 (t, J ¼ 4.74 Hz, 2H, SCH2CH2), 2.02 (t, J ¼ 3.20 Hz,
(Z)-2-(3-(3,4-Dichlorobenzyloxy)benzylidene)-6,7-dihydro-2H- 2H, NCH2CH2), 3.14 (def.t, J ¼ 5.38 Hz, 2H, SCH2), 3.72 (def.t, J
imidazo[2,1-b][1,3]thiazin-3(5H)-one (35). Product 35 was puri- ¼ 5.00 Hz, 2H, NCH2), 5.11 (s, 2H, CH2O), 6.93 (s, 1H, ArCH]),
ed by crystallization; yellow powder, mp 188–191 C (acetoni- 7.07 (dd, J ¼ 6.41 Hz, J ¼ 2.31 Hz, 1H, Ar H-40), 7.28–7.41 (m,
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trile); yield 14.94%; 1H-NMR (300 MHz; CDCl3) d: 2.23–2.31 (m, 4H, Ar H-50, H-300, H-400, H-500), 7.47 (dd, J ¼ 9.48 Hz, J ¼ 1.41
2H, SCH2CH2), 3.15 (def.t, J ¼ 5.64 Hz, 2H, SCH2), 3.73 (t, J ¼ Hz, 2H, Ar H-200, H-600), 7.71 (d, J ¼ 7.95 Hz, 1H, Ar H-20), 7.91
5.90 Hz, 2H, NCH2), 5.06 (s, 2H, CH2O), 6.90 (s, 1H, ArCH]), (d, J ¼ 1.54 Hz, 1H, Ar H-60); 13C-NMR (75 MHz; CDCl3) d: 28.16
6.94 (dd, J ¼ 7.87 Hz, J ¼ 1.03 Hz, 1H, Ar H-40), 7.26–7.32 (m, 2H, (CH2); 31.03 (CH2); 32.43 (SCH2); 41.06 (NCH2); 70.06 (CH2O);
Ar H-200, Ar H-500), 7.45 (d, J ¼ 8.20 Hz, 1H, Ar H-600), 7.53–7.57 (m, 117.48; 117.82; 125.49; 127.38; 127.77; 127.85; 128.02; 128.58;
2H, Ar H-50, H-60), 7.89–7.91 (m, 1H, Ar H-20); 13C-NMR (75 MHz; 128.76; 129.67; 135.20; 136.79; 138.94; 158.84 (ArCH]C);
CDCl3) d: 22.92 (CH2); 26.15 (SCH2); 39.86 (NCH2); 68.53 (CH2O); 164.92 (C]O); 169.60 (C]N); IR n: 1703 (C]O), 1632
116.68 (ArCH]); 117.31; 123.76; 125.51; 126.81; 129.38; 129.65; (ArCH]), 1580 (C]N), 1488, 1437, 1337, 1287, 1262, 1178,
130.53; 131.89; 132.68; 135.59; 137.26; 137.54; 158.29 (ArCH]C); 1154, 1022, 787, 748, 700; Rf ¼ 0.84; tR ¼ 8.03; purity 98.82%;
160.23 (C]O); 168.88 (C]N); IR n: 1704 (C]O), 1636 (ArCH]), MS calcd for [M + H]+: C21H20N2O2S m/z: 364.4, found 365.3;
1576 (C]N), 1488, 1465, 1357, 1230, 1180, 1163, 1040, 903, 795; anal. calcd: C 69.20, H 5.53, N 7.69, S 8.80; found: C 69.12, H
Rf ¼ 0.63; tR ¼ 8.65; purity 99.05%; MS calcd for [M + H]+: 5.66, N 7.67, S 9.14%.
C20H16N2O2Cl2S m/z: 419.33, found 419.24; anal. calcd: C 57.28,
H 3.85, N 6.68, S 7.65; found: C 57.07, H 4.11, N 6.73, S 7.58%.
(Z)-2-(3-(3-Chlorobenzyloxy)benzylidene)-5,6,7,8-tetrahy-
droimidazo[2,1-b][1,3]thiazepin-3(2H)-one (44). Product 44
(Z)-4-((3-Oxo-6,7-dihydro-3H-imidazo[2,1-b][1,3]thiazin-2(5H)- was puried by column chromatography; yellow powder, mp
ylidene)metyl)phenyl benzoate (36). Product 36 was puried by 129–131 ꢄC; yield 16%; 1H-NMR (300 MHz; DMSO-d6) d: 1.77
646 | Med. Chem. Commun., 2014, 5, 632–649
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