10.1002/ejoc.201700176
European Journal of Organic Chemistry
FULL PAPER
127.6, 127.1, 116.9, 29.3, 15.1 ; Anal. Calcd. for C16H13NO2: C, 76.48; H,
5.21; N, 5.57. found C, 76.39; H, 5.27; N, 5.59; ESI-MS (M+1) 252.2
948, 768, 689 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.25 (d, J = 8.0 Hz, 1H),
8.11 (d, J = 7.6Hz, 1H), 8.02 (d, J = 9.6 Hz, 1H), 7.85 (t, J = 7.6 Hz, 1H),
7.71 (d, J = 7.6 Hz, 1H), 7.46-7.56 (m, 2H), 7.27-7.30 (m, 1H); 13C NMR
(100 MHz, CDCl3): δ 162.9 (d, J = 245.4 Hz), 159.2, 156.0, 146.7, 136.8,
132.5(d, J = 8.1 Hz), 130.5 (d, J = 7.8 Hz), 128.7, 127.4, 124.1 (d, J = 3.2
Hz), 119.7 (d, J = 21.2 Hz), 117.1, 115.3 (d, J = 24 Hz); Anal. Calcd. for
C14H8FNO2: C, 69.71; H, 3.34; N, 5.81. found C, 69.52; H, 3.29; N, 5.95;
ESI-MS (M+1) 242.2
2-(4-Bromophenyl)-4H-benzo[d][1,3]oxazin-4-one (2e):[7] White solid;
m.p. 182-184 oC; IR (KBr) 1764, 1620, 1485, 1257, 1008, 834, 774 cm-1;
1H NMR (400 MHz, CDCl3) δ 8.25 (d, J = 7.84 Hz, 1H), 8.18 (d, J = 8.68
Hz, 2H), 7.83-7.87 (m, 1H), 7.65-7.77 (m, 3H), 7.54 (t, J = 7.24 Hz, 1H);
13C NMR (100 MHz, CDCl3): δ 159.4, 156.5, 146.9, 136.8, 132.2, 129.9,
129.3, 128.8, 128.6, 127.8, 127.4, 117.13, Anal. Calcd. for C14H8BrNO2:
C, 55.66; H, 2.67; N, 4.64. found C, 55.13; H, 2.72; N, 4.84; ESI-MS
(M+1) 303.2
2-(3-Chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one (2l):[8g] White solid;
m.p. 153-155 oC; IR (KBr) 1767, 1626, 1605, 1488, 1405, 1325, 1259,
1223, 1095, 1024, 838, 763 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.32 (s,
1H), 8.25 (d, J = 7.72 Hz, 1H), 8.2 (d, J = 7.84 Hz, 1H), 7.85 (t, J = 7.88
Hz, 1H), 7.71 (d, J = 8.08 Hz, 1H), 7.55 (t, J = 6.16 Hz, 2H), 7.46 (t, J =
7.88 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 159.1, 155.8, 146.6, 136.7,
134.9, 132.6, 132.0, 130.0, 128.7, 128.6, 128.3, 127.3, 126.3, 117.0;
Anal. Calcd. for C14H8ClNO2: C, 65.26; H, 3.13; N, 5.44. found C, 65.23;
H, 3.15; N, 5.43; ESI-MS (M+1) 258.2
2-(4-Trifluoromethylphenyl)-4H-benzo[d][1,3]oxazin-4-one
(2f):[12]
°
White solid; m.p. 126-128 C; IR (KBr) 3435, 1762, 1617, 1605, 1568,
1473, 1260, 1179, 1065, 854, 785 cm-1; 1H NMR (400 MHz, CDCl3) δ
8.37 (d, J = 8.2 Hz, 2H), 8.19-8.21 (m, 1H), 7.78-7.82 (m, 1H), 7.67-7.72
(m, 3H), 7.48-7.52 (m, 1H); 13C NMR (100 MHz, CDCl3): δ 159.1, 155.9,
146.7, 136.8, 133.7, 129.0, 128.9, 128.7, 127.6, 125.8 (q, J = 3.6 Hz),
117.3, Anal. Calcd. for C15H8F3NO2: C, 61.86; H, 2.77; N, 4.81. found C,
61.79; H, 2.71; N, 4.89; ESI-MS (M+1) 292.1
2-(3-Nitroophenyl)-4H-benzo[d][1,3]oxazin-4-one (2m): Light yellow
color solid; m.p. 162-165 oC; IR (KBr) 1766, 1621, 1595, 1519, 1356,
1319, 1067, 1035, 774, 686 cm-1; 1H NMR (400 MHz, CDCl3) δ 9.18 (s,
1H) 8.64 (d, J = 7.8 Hz, 2H), 8.43 (d, J = 8.24 Hz, 1H), 8.28 (d, J = 7.84
Hz, 1H), 7.87-7.91 (m, 1H), 7.71-7.77 (m, 2H), 7.6 (t, J = 7.24 Hz, 1H);
13C NMR (100 MHz, CDCl3): δ 158.8, 154.9, 148.8, 146.4, 137.0, 133.7,
132.3, 130.0, 129.2, 128.9, 127.6, 126.9, 123.4, 117.2; Anal. Calcd. for
C14H8N2O4: C, 62.69; H, 3.01; N, 10.44. found C, 62.51; H, 3.16; N,
10.02; ESI-MS (M+1) 269.2
2-(4-Nitrophenyl)-4H-benzo[d][1,3]oxazin-4-one (2g):[8g] Light yellow
color solid; m.p. 190-193 oC; IR (KBr) 1763, 1618, 1593, 1517, 1354,
1317, 1065, 1035, 773, 686 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.51 (d, J
= 8.68 Hz, 2H), 8.36 (d, J = 8.64 Hz, 2H), 8.28 (d, J = 7.76 Hz, 1H), 7.89
(t, J = 7.48 Hz, 1H), 7.75 (d, J = 8.08 Hz, 1H), 7.61 (t, J = 7.72 Hz, 1H);
13C NMR (100 MHz, CDCl3): δ 158.8, 155.0, 150.3, 146.4, 137.0, 136.0,
129.4, 129.3, 128.9, 127.8, 124.0, 117.2, Anal. Calcd. for C14H8N2O4: C,
62.69; H, 3.01; N, 10.44. found C, 62.58; H, 3.12; N, 10.09; ESI-MS
(M+1) 269.2
2-(2-Chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one (2n):[8g] White solid;
m.p. 136-138 oC; IR (KBr) 1768, 1625, 1475, 1440, 1315, 1272, 1223,
1092, 1029, 1003, 761cm-1; 1H NMR (400 MHz, CDCl3) δ 8.28 (d, J = 7.6
Hz, 1H), 7.90 (d, J = 6.4 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.73 (d, J = 8.4
Hz, 1H), 7.58 (t, J = 8.0 Hz, 1H), 7.53(d, J = 8.0 Hz, 1H), 7.47 (t, J = 6.0
Hz, 1H), 7.40 (t, J = 7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 159.3,
156.7, 146.6, 136.7, 133.3, 132.6, 131.6, 131.2, 130.5, 129.1, 128.7,
127.6, 127.0, 117.1; Anal. Calcd. for C14H8ClNO2: C, 65.26; H, 3.13; N,
5.44. found C, 65.21; H, 3.18; N, 5.49; ESI-MS (M+1) 258.2
2-(4-Benzoylphenyl)-4H-benzo[d][1,3]oxazin-4-one (2h): White solid;
m.p. 182-185 oC; IR (KBr) 1764, 1740, 1651, 1474, 1306, 1064, cm-1; 1H
NMR (400 MHz, CDCl3) δ 8.44 (d, J = 8.48 Hz, 2H), 8.28 (d, 7.88 Hz, 1H),
7.93 (d, J = 8.48 Hz, 2H), 7.82-7.89 (m, 3H), 7.74 (d, J = 8.0, 1H), 7.64 (t,
J = 7.36 Hz, 1H), 7.52-7.59 (m, 3H); 13C NMR (100 MHz, CDCl3): δ 195.9,
159.2, 156.2, 146.7, 140.9, 137.0, 136.7, 133.5, 132.9, 130.2, 130.1,
128.8, 128.7, 128.5, 128.2, 127.5, 117.1; Anal. Calcd. for C21H13NO3: C,
77.05; H, 4.0; N, 4.28. found C, 77.10; H, 4.24; N, 4.29; ESI-MS (M+1)
328.2
2-(3,5-Dimethoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one (2o): white
solid; m.p. 174-176 °C; IR (KBr) 2972, 1752, 1603, 1568, 1478, 1301,
1178, 1025, 832, 783 cm-1 1H NMR (400 MHz, CDCl3) δ 8.24 (dd, J = 6.8
Hz, 1.2 Hz, 1H), 7.81-7.85 (m, 1H), 7.72 (t, J = 7.2 Hz, 1H), 7.51-7.54 (m,
1H), 7.47 (d, J = 2.0 Hz, 2H), 6.67 (t, J = 2.4 Hz, 1H), 3.89 (s, 6H); 13C
NMR (100 MHz, DMSO-d6): δ 161.2, 159.2, 156.4, 146.5, 137.4, 132.4,
129.2, 128.5, 127.4, 117.4, 105.9, 105.3, 56.1; Anal. Calcd. for
C16H13NO4: C, 67.84; H, 4.63; N, 4.94. found C, 67.79; H, 4.69; N, 4.91;
ESI-MS (M+1) 284.2
2-(3-Methylphenyl)-4H-benzo[d][1,3]oxazin-4-one (2i):[12] White solid;
m.p. 108-110 oC; IR (KBr) 1747, 1607, 1578, 1495, 1446, 1307, 836, 686
cm-1; 1H NMR (400 MHz, CDCl3) δ 8.25 (dd, J = 7.88 Hz, 1.12 Hz, 1H),
8.12 (t, J = 6.2 Hz, 2H), 7.81-7.86 (m, 1H), 7.7 (d, J = 7.96 Hz, 1H), 7.50-
7.54 (m, 1H), 7.41 (t, J = 6.04 Hz, 2H), 2.46 (s, 3H), 13C NMR (100 MHz,
CDCl3): δ 159.7, 157.4, 147.1, 138.7, 136.6, 133.6, 130.2, 128.8, 128.7,
128.6, 128.2, 127.3, 125.6, 117.1, 21.4; Anal. Calcd. for C15H11NO2: C,
75.94; H, 4.67; N, 5.90. found C, 75.86; H, 4.61; N, 5.81; ESI-MS (M+1)
238.2
2-(3,4,5-Trimethoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one
(2p):[11]
white solid; m.p. 178-180 oC; IR (KBr) 2974, 1755, 1605, 1566, 1475,
1303, 1175, 1027, 832, 785 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.24 (d, J
= 7.88 Hz, 1H), 7.81-7.86 (m, 1H), 7.7 (d, J = 7.96 Hz, 1H), 7.50-7.57 (m,
3H), 3.99 (s, 6H), 3.92 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 159.7,
156.9, 153.4, 147.1, 142.2, 136.7, 128.7, 128.2, 127.2, 125.3, 116.8,
105.6, 104.8, 61.1, 56.1; Anal. Calcd. for C17H15NO5: C, 65.17; H, 4.83; N,
4.47. found C, 65.09; H, 4.94; N, 4.41; ESI-MS (M+1) 314.2
2-(3-Methoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one (2j):[10a]
White
solid; m.p. 114-116 oC; IR (KBr) 2971, 1604, 1567, 1506, 1305, 1285,
1176, 1047, 831, 781 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.17-8.19 (m,
1H), 7.85 (d, J = 7.8 Hz, 1H), 7.74-7.79 (m, 2H), 7.63 (d, J = 8.04 Hz, 1H),
7.46 (t, J = 7.24 Hz, 1H), 7.35 (t, J = 7.96 Hz, 1H), 7.04-7.07 (m, 1H), 3.8
(s, 3H); 13C NMR (100 MHz, CDCl3): δ 160.0, 159.6, 157.1, 147.0, 136.7,
131.6, 129.9, 128.7, 128.4, 127.4, 121.0, 119.5, 117.1, 112.7, 55.7; Anal.
Calcd. for C15H11NO3: C, 71.14; H, 4.38; N, 5.53. found C, 71.48; H, 4.21;
N, 5.69; ESI-MS (M+1) 254.2
2-(Thiophen-2-yl)-4H-benzo[d][1,3]oxazin-4-one (2q):[12] White solid;
m.p. 128-130 oC; IR (KBr) 1775, 1619, 1600, 1473, 1424, 1221, 1026,
777, 716 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.22 (d, 7.88 Hz, 1H), 7.97
(d, J = 2.92 Hz, 1H), 7.79-7.83 (m, 1H), 7.61-7.65 (m, 2H), 7.49 (t, J =
7.28 Hz, 1H), 7.18 (t, J = 4.68 Hz, 1H), 13C NMR (100 MHz, CDCl3): δ
2-(3-Fluorophenyl)-4H-benzo[d][1,3]oxazin-4-one (2k):[9] White solid;
m.p. 138-142 oC; IR (KBr) 1759, 1607, 1588, 1446, 1325, 1278, 1008,
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