E
X.-Y. Chen et al.
Paper
Synthesis
13C NMR (100 MHz, CDCl3): δ = 161.2 (d, JF-C = 256.2 Hz), 160.2 (d, JF-C
4.1 Hz), 153.8, 140.2, 139.8 (d, JF-C = 5.3 Hz), 134.1, 130.9, 130.7 (d, JF-C
10.2 Hz), 130.3, 129.4, 129.0, 128.6, 128.53, 128.51, 128.3, 128.0,
127.1, 126.7, 125.4, 122.3, 116.4 (d, JF-C = 3.5 Hz), 114.0 (d, JF-C = 21.7
Hz), 113.0 (d, JF-C = 12.6 Hz).
=
=
1H NMR (400 MHz, CDCl3): δ = 8.17 (dd, J = 8.0, 2.0 Hz, 1 H, ArH), 7.59
(d, J = 7.2 Hz, 2 H, ArH), 7.44–7.39 (m, 2 H, ArH), 7.36–7.20 (m, 10 H,
ArH), 6.81 (dd, J = 8.8, 2.4 Hz, 1 H, ArH), 6.50 (d, J = 8.4 Hz, 1 H, ArH).
13C NMR (100 MHz, CDCl3): δ = 157.9, 153.5, 145.1, 140.4, 134.1,
133.2, 131.3, 130.7, 130.2, 129.9, 129.2, 128.9, 128.64, 128.56, 128.3,
128.0, 127.2, 127.0, 126.2, 125.3, 123.1, 123.0, 120.5.
HRMS (ESI): m/z [M + H]+ calcd for C27H18FN2O: 405.1398; found:
405.1382.
HRMS (ESI): m/z [M + H]+ calcd for C27H18ClN2O: 421.1102; found:
421.1119.
6-Methyl-2,3-diphenyldibenzo[b,f]imidazo[1,2-d][1,4]oxazepine
(3i)
6,12-Dichloro-2,3-diphenyldibenzo[b,f]imidazo[1,2-d][1,4]oxaze-
Yield: 172 mg (86%); white solid; mp 231–232 °C.
pine (3m )
IR (KBr): 3059, 3028, 2918, 1600, 1574, 1525, 1497, 1476, 1462, 1445,
Yield: 198 mg (87%); white solid; mp 205–206 °C.
1422, 1321, 1217, 1176, 1073, 962, 915, 820, 776, 757, 713, 700 cm–1
.
IR (KBr): 3051, 3021, 1528, 1491, 1458, 1446, 1407, 1364, 1248, 1222,
1H NMR (400 MHz, CDCl3): δ = 8.16 (d, J = 7.2 Hz, 1 H, ArH), 7.59 (d, J =
7.6 Hz, 2 H, ArH), 7.42–7.21 (m, 12 H, ArH), 6.63 (d, J = 8.4 Hz, 1 H,
ArH), 6.46 (d, J = 8.4 Hz, 1 H, ArH), 2.28 (s, 3 H, CH3).
13C NMR (100 MHz, CDCl3): δ = 158.5, 153.1, 145.4, 140.1, 138.7,
134.4, 131.0, 130.8, 130.6, 129.8, 129.02, 128.99, 128.96, 128.3, 128.0,
127.2, 127.0, 126.0, 125.8, 125.7, 123.5, 122.8, 120.5, 21.0.
1111, 1084, 1073, 960, 908, 821, 783, 774, 704 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 8.15 (d, J = 2.4 Hz, 1 H, ArH), 7.57 (d, J =
6.8 Hz, 2 H, ArH), 7.40 (d, J = 2.0 Hz, 1 H, ArH), 7.38–7.34 (m, 4 H,
ArH), 7.31–7.23 (m, 6 H, ArH), 6.84 (dd, J = 8.8, 2.4 Hz, 1 H, ArH), 6.52
(d, J = 8.8 Hz, 1 H, ArH).
13C NMR (100 MHz, CDCl3): δ = 156.2, 153.1, 143.9, 140.7, 133.8,
133.4, 131.7, 131.0, 130.7, 129.9, 129.4, 129.3, 129.3, 128.8, 128.4,
127.9, 127.4, 127.0, 125.6, 124.6, 123.0, 121.9.
HRMS (ESI): m/z [M + H]+ calcd for C28H21N2O: 401.1648; found:
401.1651.
HRMS (ESI): m/z [M + H]+ calcd for C27H17Cl2N2O: 455.0712; found:
455.0695.
12-Chloro-6-methyl-2,3-diphenyldibenzo[b,f] imidazo[1,2-
d][1,4]oxazepine (3j)
Yield: 183 mg (84%); white solid; mp 236–237 °C.
6-Chloro-12-methoxy-2,3-diphenyldibenzo[b,f]imidazo[1,2-
d][1,4]oxazepine (3n)
IR (KBr): 3052, 3028, 2913, 1501, 1478, 1457, 1443, 1421, 1373, 1262,
1218, 1108, 1025, 961, 838, 786, 717 cm–1
.
Yield: 185 mg (82%); white solid; mp 213–214 °C.
1H NMR (400 MHz, CDCl3): δ = 8.14 (d, J = 2.0 Hz, 1 H, ArH), 7.60 (d, J =
7.6 Hz, 2 H, ArH), 7.36–7.22 (m, 11 H, ArH), 6.97 (d, J = 8.4 Hz, 1 H,
ArH), 6.36 (s, 1 H, ArH), 1.94 (s, 3 H, CH3).
IR (KBr): 3053, 3003, 2974, 1533, 1489, 1480, 1463, 1446, 1435, 1408,
1368, 1305, 1287, 1262, 1214, 1193, 1110, 1057, 1038, 961, 916, 876,
813, 736 cm–1
.
13C NMR (100 MHz, CDCl3): δ = 157.0, 150.9, 144.2, 140.3, 135.2,
134.1, 131.1, 130.8, 130.7, 130.4, 129.4, 129.3, 129.1, 129.0, 128.8,
128.5, 128.4, 128.0, 127.2, 127.1, 124.9, 121.9, 121.8, 20.7.
HRMS (ESI): m/z [M + H]+ calcd for C28H20ClN2O: 435.1259; found:
435.1242.
1H NMR (400 MHz, CDCl3): δ = 7.64 (d, J = 3.2 Hz, 1 H, ArH), 7.60–7.58
(m, 2 H, ArH), 7.40 (d, J = 2.0 Hz, 1 H, ArH), 7.36–7.35 (m, 3 H, ArH),
7.31–7.22 (m, 6 H, ArH), 6.94 (dd, J = 8.8, 3.2 Hz, 1 H, ArH), 6.81 (dd,
J = 8.8, 2.4 Hz, 1 H, ArH), 6.50 (d, J = 8.8 Hz, 1 H, ArH), 3.89 (s, 3 H,
CH3).
13C NMR (100 MHz, CDCl3): δ = 157.4, 153.9, 151.8, 145.1, 140.4,
134.1, 133.2, 130.7, 130.2, 129.2, 129.1, 128.62, 128.59, 128.4, 128.0,
127.3, 127.0, 125.2, 123.6, 122.8, 121.5, 118.0, 112.9, 56.0.
12-Methoxy-6-methyl-2,3-diphenyldibenzo[b,f] imidazo[1,2-
d][1,4]oxazepine (3k)
HRMS (ESI): m/z [M + H]+ calcd for C28H20ClN2O: 451.1208; found:
Yield: 179 mg (83%); white solid; mp 239–240 °C.
451.1209.
IR (KBr): 3067, 3040, 2996, 2950, 2835, 1612, 1576, 1518, 1494, 1464,
1378, 1247, 1199, 1110, 1035, 835, 822, 768 cm–1
.
6-Methoxy-2,3-diphenyldibenzo[b,f]imidazo[1,2-d][1,4]oxaze-
pine (3o)
1H NMR (400 MHz, CDCl3): δ = 7.64–7.61 (m, 3 H, ArH), 7.35–7.20 (m,
10 H, ArH), 6.96 (d, J = 8.0 Hz, 1 H, ArH), 6.92 (dd, J = 8.8, 2.8 Hz, 1 H,
ArH), 6.35 (s, 1 H, ArH), 3.88 (s, 3 H, CH3), 1.94 (s, 3 H, CH3).
Yield: 181 mg (87%); white solid; mp 171–172 °C.
IR (KBr): 3050, 3025, 2867, 1601, 1572, 1527, 1491, 1459, 1406, 1301,
13C NMR (100 MHz, CDCl3): δ = 157.1, 152.6, 151.7, 145.4, 140.0,
134.7, 134.4, 130.8, 130.7, 129.3, 129.2, 129.0, 128.9, 128.7, 128.3,
128.0, 127.1, 127.0, 123.9, 121.7, 121.4, 117.8, 112.8, 56.0, 20.7.
HRMS (ESI): m/z [M + H]+ calcd for C29H23N2O2: 431.1754; found:
431.1751.
1249, 1142, 1072, 1028, 980, 958, 908, 878, 820, 753, 705 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 8.17 (d, J = 8.0 Hz, 1 H, ArH), 7.63–7.61
(m, 2 H, ArH), 7.42–7.23 (m, 12 H, ArH), 6.70 (dd, J = 8.8, 2.8 Hz, 1 H,
ArH), 6.08 (d, J = 2.8 Hz, 1 H, ArH), 3.22 (s, 3 H, OCH3).
13C NMR (100 MHz, CDCl3): δ = 158.8, 156.2, 146.8, 145.6, 140.1,
134.2, 131.1, 130.88, 130.86, 130.0, 129.9, 129.2, 128.8, 128.4, 128.3,
127.9, 127.1, 125.8, 123.4, 122.8, 120.4, 114.9, 110.6, 55.4.
6-Chloro-2,3-diphenyldibenzo[b,f]imidazo[1,2-d][1,4]oxazepine
(3l)
HRMS (ESI): m/z [M + H]+ calcd for C28H21N2O2: 417.1598; found:
Yield: 179 mg (85%); white solid; mp 231–232 °C.
417.1608.
IR (KBr): 3055, 3003, 1601, 1540, 1530, 1506, 1476, 1458, 1419, 1386,
1255, 1218, 1110, 1027, 960, 951, 858, 820, 783, 760 cm–1
.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2019, 51, A–G