10.1002/ejoc.201901687
European Journal of Organic Chemistry
(m, 4H, ArH), 7.51 (d, J = 8.4 Hz, 2H, ArH), 7.73 (d, J = 8.8 Hz,
2H, ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ 24.2, 78.5, 127.3,
127.5, 128.3, 128.4, 128.6, 128.7, 128.8, 129.4, 131.5, 131.9,
134.2, 141.0, 162.5, 181.0. IR (neat) ν 3258, 1755, 1615, 1575,
1491, 1333, 1154, 1072, 768, 695 cm-1. HRMS (ESI) calcd. for
C22H19BrN3O3S (M+H): 484.0325, Found: 484.0332.
5H, ArH), 7.39 (t, J = 7.2 Hz, 1H, ArH), 7.77 (d, J = 8.0 Hz, 2H,
ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ 21.2, 21.5, 24.3, 78.3,
127.2, 127.3, 128.2, 128.7, 128.9, 129.3, 130.0, 131.2, 131.7,
138.5, 139.1, 143.2, 162.4, 185.4. IR (neat) ν 3279, 1757, 1623,
1579, 1514, 1336, 1297, 1153, 1089, 1006, 888, 812, 757, 668
cm-1. HRMS (ESI) calcd. for C24H24N3O3S (M+H): 434.1533,
Found: 434.1538.
Compound 3la: A white solid, 59.2 mg, 72% yield. M.P.: 198-201
oC. 1H NMR (CDCl3, TMS, 400 MHz) δ 1.73 (s, 3H, CH3), 6.32 (s,
1H, NH), 6.97-6.99 (m, 1H, ArH), 7.18-7.20 (m, 2H, ArH), 7.26 (t,
J = 7.2 Hz, 2H, ArH), 7.34-7.43 (m, 6H, ArH), 7.51-7.52 (m, 1H,
ArH), 7.63-7.65 (m, 1H, ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ
24.4, 78.5, 126.9, 127.3, 128.2, 128.51, 128.54, 128.8, 129.4,
131.3, 132.0, 132.6, 134.2, 143.0, 162.7, 180.7. IR (neat) ν 3265,
1761, 1624, 1491, 1447, 1336, 1301, 1154, 1021, 774 cm-1.
HRMS (ESI) calcd. for C20H18N3O3S2 (M+H): 412.0784, Found:
412.0792.
Compound 3ac: A white solid, 80.8 mg, 90% yield. M.P.: 102-
o
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104 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.69 (s, 3H, CH3),
2.37 (s, 3H, CH3), 3.79 (s, 3H, OCH3), 6.62 (s, 1H, NH), 6.89 (d, J
= 8.8 Hz, 2H, ArH), 7.13-7.20 (m, 4H, ArH), 7.25 (t, J = 8.0 Hz,
2H, ArH), 7.31 (d, J = 7.2 Hz, 2H, ArH), 7.39 (t, J = 7.2 Hz, ArH),
7.77 (d, J = 8.4 Hz, 2H, ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ
20.5, 23.3, 54.4, 77.1, 113.6, 126.0, 126.2, 127.2, 127.63, 127.64,
127.8, 128.3, 130.2, 138.0, 142.2, 158.4, 161.5, 180.4. IR (neat) ν
3241, 1757, 1609, 1597, 1510, 1297, 1247, 1152, 1091, 1029,
813, 668 cm-1. HRMS (ESI) calcd. for C24H24N3O4S (M+H):
450.1482, Found: 450.1488.
Compound 3ma: A white solid, 63.0 mg, 75% yield. M.P.: 244-
o
1
246 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.70 (s, 3H, CH3),
2.38 (s, 3H, CH3), 6.64 (s, 1H, NH), 7.15-7.24 (m, 6H, ArH), 7.36-
Compound 3ad: A white solid, 77.0 mg, 85% yield. M.P.: 100-
7.44 (m, 5H, ArH), 7.64 (d, J = 8.0 Hz, 1H, ArH), 8.56 (s, 1H, ArH). 102 oC. 1H NMR (CDCl3, TMS, 400 MHz) δ 1.69 (s, 3H,CH3), 2.37
13C NMR (CDCl3, TMS, 100 MHz) δ 18.5, 24.0, 78.1, 121.1, 127.3, (s, 3H, CH3), 6.74 (s, 1H, NH), 7.14-7.20 (m, 4H, ArH), 7.27-7.28
128.1, 128.4, 128.5, 128.7, 129.3, 131.2, 134.3, 137.1, 137.6,
150.3, 156.1, 162.2, 180.3. IR (neat) ν 3093, 1754, 1595, 1493,
1446, 1337, 1305, 1164, 1104, 704, 672 cm-1. HRMS (ESI) calcd.
for C22H21N4O3S (M+H): 421.1329, Found: 421.1336.
(m, 4H, ArH), 7.35 (d, J = 8.8 Hz, 2H, ArH), 7.40-7.44 (m, 1H,
ArH), 7.76 (d, J = 8.4 Hz, 2H, ArH). 13C NMR (CDCl3, TMS, 100
MHz) δ 21.5, 24.1, 78.4, 127.2, 128.3, 128.4, 128.7, 128.8, 129.3,
129.6, 131.5, 132.9, 134.3, 139.0, 143.4, 161.9, 181.0. IR (neat) ν
3257, 1759, 1611, 1597, 1491, 1305, 1152, 1089, 1004, 891, 812,
699, 668 cm-1. HRMS (ESI) calcd. for C23H21ClN3O3S (M+H):
454.0987, Found: 454.0994.
Compound 3na: A white solid, 44.6 mg, 65% yield. M.P.: 172-
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174 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.71 (s, 3H, CH3),
3.16 (s, 3H, CH3), 6.13 (s, 1H, NH), 7.14-7.16 (m, 2H, ArH), 7.27-
7.31 (m, 2H, ArH), 7.34-7.44 (m, 6H, ArH). 13C NMR (CDCl3, TMS, Compound 3ae: A white solid, 51.7 mg, 57% yield. M.P.: 118-
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100 MHz) δ 24.4, 44.3, 78.2, 127.3, 128.3, 128.5, 128.6, 128.7,
129.3, 131.4, 134.1, 163.0, 181.0. IR (neat) ν 3534, 1752, 1624,
1595, 1498, 1331, 1309, 1148, 1131, 975, 776, 696 cm-1. HRMS
(ESI) calcd. for C17H18N3O3S (M+H): 344.1063, Found: 344.1071.
120 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.69 (s, 3H, CH3),
2.37 (s, 3H, CH3), 6.66 (s, 1H, NH), 7.05-7.07 (m, 1H, ArH), 7.20
(d, J = 8.0 Hz, 2H, ArH), 7.27-7.29 (m, 6H, ArH), 7.31-7.33 (m, 1H,
ArH), 7.41-7.45 (m, 1H, ArH), 7.77 (d, J = 8.4 Hz, 2H, ArH). 13C
NMR (CDCl3, TMS, 100 MHz) δ 21.6, 24.2, 78.4, 125.7, 127.2,
127.6, 128.3, 128.4, 128.8, 129.4, 130.3, 131.5, 134.8, 135.5,
138.9, 143.4, 161.7, 180.8. IR (neat) ν 3194, 1745, 1590, 1478,
1309, 1155, 1093, 997, 893, 762, 668 cm-1. HRMS (ESI) calcd.
for C23H21ClN3O3S (M+H): 454.0987, Found: 454.0990.
Compound 3oa: A white solid, 47.8 mg, 57% yield. M.P.: 227-
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229 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.70 (s, 3H, CH3),
2.38 (s, 3H, CH3), 6.20 (s, 1H, NH), 7.19-7.22 (m, 4H, ArH), 7.25-
7.30 (m, 4H, ArH), 7.35-7.40 (m, 4H, ArH), 7.78 (d, J = 8.4 Hz, 2H,
ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ 21.5, 24.4, 78.3, 127.3,
127.4, 128.2, 128.5, 128.6, 128.8, 129.3, 129.4, 131.3, 134.4,
139.0, 143.4, 162.3, 180.9. IR (neat) ν 3250, 1754, 1619, 1592,
1490, 1329, 1315, 1300, 1151, 778, 696, 669 cm-1. HRMS (ESI)
calcd. for C23H22N3O3S (M+H): 420.1376, Found: 420.1384.
Compound 3ai: A white solid, 62.4 mg, 72% yield. M.P.: 198-200
oC. 1H NMR (CDCl3, TMS, 400 MHz) δ 1.69 (s, 3H, CH3), 2.31 (s,
3H, CH3), 2.37 (s, 3H, CH3), 6.70 (s, 1H, NH), 7.03 (d, J = 8.0 Hz,
2H, ArH), 7.15-7.22 (m, 6H. ArH), 7.35-7.41 (m, 3H, ArH), 7.77 (d,
J = 8.0 Hz, 2H, ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ 21.5,
21.5, 24.3, 78.3, 125.7, 127.3, 127.5, 128.5, 128.8, 128.9, 129.3,
129.3, 134.5, 139.1, 141.8, 143.2, 162.2, 181.2. IR (neat) ν 3252,
1752, 1628, 1491, 1330, 1301, 1151, 894, 810, 768, 698, 673 cm-
1. HRMS (ESI) calcd. for C24H24N3O3S (M+H): 434.1533, Found:
434.1540.
Compound 3pa: A white solid, 26.8 mg, 32% yield. M.P.: 227-
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229 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.68 (s, 3H, CH3),
2.36 (s, 3H, CH3), 5.83 (s, 1H, NH), 7.17-7.21 (m, 4H, ArH), 7.23-
7.29 (m, 4H, ArH), 7.34-7.39 (m, 4H, ArH), 7.76 (d, J = 8.4 Hz, 2H,
ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ 21.5, 24.4, 78.3, 127.3,
127.4, 128.2, 128.5, 128.6, 128.8, 129.3, 129.4, 131.3, 134.4,
139.0, 143.4, 162.3, 180.9. IR (neat) ν 3250, 1754, 1619, 1592,
1490, 1329, 1315, 1300, 1151, 778, 696, 669 cm-1. HRMS (ESI)
calcd. for C23H22N3O3S (M+H): 420.1376, Found: 420.1384.
Compound 3aj: A white solid, 65.6 mg, 73% yield. M.P.: 227-229
oC. 1H NMR (CDCl3, TMS, 400 MHz) δ 1.68 (s, 3H, CH3), 2.39 (s,
3H, CH3), 3.79 (s, 3H, OCH3), 6.22 (s, 1H, NH), 6.73 (d, J = 9.2
Hz, 2H, ArH), 7.19-7.24 (m, 6H, ArH), 7.37-7.43 (m, 3H, ArH),
7.77 (d, J = 8.0 Hz, 2H, ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ
21.6, 24.5, 55.3, 78.2, 113.6, 120.7, 127.3, 127.5, 128.5, 129.3,
129.4, 130.7, 134.7, 139.0, 143.3, 161.8, 161.9, 181.1. IR (neat) ν
3172, 1727, 1599, 1509, 1318, 1303, 1262, 1173, 1153, 1088,
1029, 806, 768, 665, 717 cm-1. HRMS (ESI) calcd. for
C24H24N3O4S (M+H): 450.1482, Found: 450.1491.
Compound 3qa: A white solid, 52.8 mg, 63% yield. M.P.: 227-
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229 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.69 (s, 3H, CH3),
2.38 (s, 3H, CH3), 6.20 (s, 1H, NH), 7.19-7.22 (m, 4H, ArH), 7.25-
7.30 (m, 4H, ArH), 7.35-7.40 (m, 4H, ArH), 7.78 (d, J = 8.4 Hz, 2H,
ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ 21.5, 24.4, 78.3, 127.3,
127.4, 128.2, 128.5, 128.6, 128.8, 129.3, 129.4, 131.3, 134.4,
138.9, 143.3, 162.3, 180.9. IR (neat) ν 3250, 1754, 1619, 1592,
1490, 1329, 1315, 1300, 1151, 778, 696, 669 cm-1. HRMS (ESI)
calcd. for C23H22N3O3S (M+H): 420.1376, Found: 420.1384.
Compound 3ak: A white solid, 87.5 mg, 88% yield. M.P.: 114-
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1
116 C. H NMR (CDCl3, TMS, 400 MHz) δ 1.69 (s, 3H, CH3),
2.39 (s, 3H, CH3), 6.10 (s, 1H, NH), 7.16 (d, J = 8.4 Hz, 2H, ArH),
7.21 (t, J = 8.4 Hz, 4H, ArH), 7.38-7.42 (m, 5H, ArH), 7.76 (d, J =
8.0 Hz, 2H, ArH). 13C NMR (CDCl3, TMS, 100 MHz) δ 21.6, 24.3,
78.3, 126.2, 127.2, 127.4, 127.5, 128.8, 129.4, 129.5, 130.3,
131.5, 134.1, 138.9, 143.5, 161.5, 180.8. IR (neat) ν 3526, 1755,
Compound 3ab: A white solid, 68.4 mg, 79% yield. M.P.: 94-96
oC. 1H NMR (CDCl3, TMS, 400 MHz) δ 1.69 (s, 3H, CH3), 2.35 (s,
3H, CH3), 2.37 (s, 3H, CH3), 7.08-7.20 (m, 6H, ArH), 7.22-7.32 (m,
5
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