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ACCEPTED MANUSCRIPT
1-Ethyl-3,6-diphenyl-1,3-diazinane-2,4-dione (11d) (91.1 mg, 75%). White solid, mp 147-148 °C.
Chromatography (CH2Cl2 : CHCl3 2:1). Rf: 0.9 (UV active, CH2Cl2 : AcOEt = 3:2). IR (neat) ν (cm−1):
2980, 1710, 1671, 1458, 1435, 1350, 1212, 1194. 1H NMR (CDCl3, 700 MHz) δ 1.21 (t, 3H, J = 7.2 Hz),
3.10 (q, 1H, J = 7.2 Hz), 3.10 (q, 1H, J= 7.1 Hz), 3.98 (q, 1H, J = 7,2 Hz), 5.24 (s, 1H), 5.81 (s, 1H), 6.38 (s,
1H), 7.17-7.19 (m, 2H), 7.30-7.33 (m, 2H), 7.35 (tt, 1H, J = 7.4, 1.3 Hz), 7.39 (tt, 1H, J = 7.4, 1.3 Hz),
7.43-7.47 (m, 2H). 13C NMR (CDCl3, 176 MHz) δ 13.15, 42.56, 61.43, 125.10, 125.83, 128.41, 128.57,
128.77, 129.05, 129.33, 135.62, 136.77, 152.59, 162.71. ESI-MS [M+H]+ = 307, [2M+Na]+ = 635. Anal.
Calcd for C19H18N2O2: C, 74.49%, H, 5.92%, N, 9.14%. Found: C, 74.37%, H, 5.90%, N, 9.11%.
1-Ethyl-3-(4-methoxyphenyl)-6-methyl-1,3-diazinane-2,4-dione (11e) (84.5 mg, 77%). Light yellow
oil, mp 117-118 °C. Chromatography (CH2Cl2 : CHCl3 1:1). Rf: 0.8 (UV active, CH2Cl2 : AcOEt = 2:3). IR
1
(neat) ν (cm−1): 2972, 1709, 1670, 1510, 1464, 1432, 1352, 1254, 1215, 1188. H NMR (CDCl3, 700
MHz) δ 1.24 (t, 3H, J = 7.1 Hz), 1.46 (d, 3H, J = 6.7 Hz), 3.17 (q, 1H, J = 7.1 Hz), 3.83 (q, 1H, J = 7.1 Hz),
4.21 (q, 1H, J = 6.6 Hz), 5.62 (s, 1H), 6.31 (s, 1H), 6.97-7.00 (m, 2H), 7.12-7.15 (m, 2H). 13C NMR (CDCl3,
176 MHz) δ 13.48, 21.83, 41.81, 53.78, 55.44, 114.35, 123.65, 128.37, 129.75, 137.27, 151.40,
159.08, 163.13. ESI-MS [M+H]+ = 275, [2M+Na]+ = 571. Anal. Calcd for C15H18N2O3: C, 65.68%, H,
6.61%, N, 10.21%. Found: C, 65.82% H, 6.55%, N, 10.15%.
1,6-Diethyl-3-(4-methoxyphenyl)-1,3-diazinane-2,4-dione (11f) (111 mg, 96%). Light yellow oil, mp
117-118 °C. Chromatography (CH2Cl2 : CHCl3 1:1). Rf: 0.8 (UV active, CH2Cl2 : AcOEt = 2:3). IR (neat) ν
(cm−1): 2968, 1709, 1669, 1511, 1461, 1435, 1245, 1214, 1187, 1029. 1H NMR (CDCl3, 700 MHz) δ 0.94
(t, 3H, J = 7.1 Hz), 1.23 (t, 3H, J = 7.1 Hz), 1.65-1.92 (m, 2H), 3.15 (q, 2H, J = 7.1 Hz), 3.84 (s, 3H), 3.90
(q, 2H, J = 7.2 Hz), 3.95 (bs, 1H), 5.57 (s, 1H), 6.37 (s, 1H), 6.95-7.00 (m, 2H), 7.09-7.15 (m, 2H). 13C
NMR (CDCl3, 176 MHz) δ 9.42, 13.42, 27.62, 42.26, 55.44, 59.46, 114.34, 124.75, 128.34, 129.68,
135.63, 152.11, 159.23, 163.56. ESI-MS [M+H]+ = 289, [2M+Na]+ = 599. Anal. Calcd for C16H20N2O3: C,
66.65%, H, 6.99%, N, 9.72%. Found: C, 66.41% H, 7.06%, N, 9.69%.
1-Ethyl-3-(4-methoxyphenyl)-6-(propan-2-yl)-1,3-diazinane-2,4-dione (11g) (111 mg, 92%).
Colourless oil. Chromatography (CH2Cl2 : CHCl3 1:1). Rf: 0.8 (UV active, CH2Cl2 : AcOEt = 1:1). IR (neat)
1
ν (cm−1): 2966, 1703, 1654, 1510, 1457, 1242, 1218, 1195, 1033, 954. H NMR (CDCl3, 700 MHz) δ
0.96 (d, 3H, J = 6,9 Hz), 0.99 (d, 6H, J = 6.9 Hz), 1.22 (t, 3H, J = 7.1 Hz), 2.15 (oktet, 1H, J = 6.9 Hz), 3.11
(q, 1H, J = 7,1 Hz), 3.80 (s, 3H), 3.84 (d, 1H, J = 5.0 Hz), 3.94 (q, 1H, J = 7.1 Hz), 5.54 (s, 1H), 6.41 (s,
1H), 6.96-6.98 (m, 2H), 7.10-7.12 (m, 2H). 13C NMR (CDCl3, 176 MHz) δ 13.27, 16.94, 18.90, 32.34,
43.20, 55.44, 63.64, 114.31, 125.87, 128.31, 129.52, 133.68, 152.23, 159.21, 164.00. ESI-MS [M+H]+ =
303, [M+Na]+ = 627. Anal. Calcd for C17H22N2O3: C, 67.53%, H, 7.33%, N, 9.26%. Found: C, 67.40% H,
7.39%, N, 9.24%.
1-Ethyl-6-phenyl-3-(4-methoxyphenyl)-1,3-diazinane-2,4-dione (11h) (99.6 mg, 74%). White solid,
mp 147-148 °C. Chromatography (CH2Cl2 : CHCl3 2:1). Rf: 0.9 (UV active, CH2Cl2 : AcOEt = 1:1). IR
1
(neat) ν (cm−1): 2921, 1710, 1670, 1511, 1463, 1434, 1246, 1215, 1030. H NMR (CDCl3, 700 MHz) δ
1.21 (t, 3H, J = 7.1 Hz), 3.10 (q, 1H, J = 7.1 Hz), 3.82 (s, 3H), 3.97 (q, 1H, J = 7.1 Hz), 5.22 (bs, 1H), 5.79
(s, 1H), 6.37 (s, 1H), 6.94-6.97 (m, 2H), 7.07-7.10 (m, 2H), 7.28-7.31 (m, 2H), 7.35 (tt, 1H, J = 7.4, 1.2
Hz), 7.39-7.41 (m, 2H). 13C NMR (CDCl3, 176 MHz) δ 13.28, 42.70, 55.58, 61.52, 55.44, 114.53, 125.08,
125.94, 128.32, 128.65, 129.42, 129.78, 136.94, 138.98, 159.20, 159.45, 162.03. ESI-MS [M+H]+ =
337, [M+Na]+ = 695. Anal. Calcd for C20H20N2O3: C, 71.41%, H, 5.99%, N, 8.33%. Found: C, 71.25% H,
6.02%, N, 8.25%.
3-(4-Bromophenyl)-1-ethyl-6-methyl-1,3-diazinane-2,4-dione (11i) (106 mg, 82%). White solid, mp
119-120 °C. Chromatography (CH2Cl2 : CHCl3 1:1). Rf: 0.8 (UV active, CH2Cl2 : AcOEt = 1:1). IR (neat) ν
(cm−1): 2973, 1705, 1674, 1463, 1434, 1353, 1249, 1216, 1195, 1011, 970. 1H NMR (CDCl3, 700 MHz) δ
1.24 (t, 3H, J = 7.0 Hz), 1.46 (d, 3H, J = 6.7 Hz), 3.17 (q, 1H, J = 7.0 Hz), 3.83 (q, 1H, J = 7.0 Hz), 4.22 (q,
1H, J = 6.7 Hz), 5.64 (s, 1H), 6.32 (s, 1H), 7.05-7.09 (m, 2H), 7.54-7.58 (m, 2H). 13C NMR (CDCl3, 176
MHz) δ 13.46, 21.90, 41.85, 53.81, 122.29, 124.1, 130.64, 132.18, 134.74, 137.56, 151.40, 162.90.