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N. Bagi et al.
2-Phenylphenanthro[9,10-d][1,3]oxazole
2-(4-Chlorophenyl)phenanthro[9,10-d][1,3]oxazole
(2a, C21H13NO)
(2e, C21H12ClNO)
Yellow crystals; 78 % yield; m.p.: 192–199 °C; Rf = 0.58
(hexan/diethyl ether 9/1); 1H NMR (400 MHz, CDCl3):
d = 8.73 (app. t, J = 16.4 Hz, 2H), 8.63 (d, J = 7.6 Hz,
1H), 8.32–8.39 (m, 3H), 7.77–7.52 (m, 7H) ppm; 13C NMR
(100 MHz, CDCl3): d = 162.11, 144.83, 135.51, 130.85,
129.25, 128.86, 127.55, 127.35, 127.20, 127.13, 126.33,
126.16, 126.07, 123.68, 123.36, 122.90, 121.04,
Yellow crystals; 52 % yield; m.p.: 258–260 °C; Rf = 0.57
(hexan/diethyl ether 9/1); 1H NMR (400 MHz, CDCl3):
d = 8.74(app. t, J = 18.8 Hz, 2H), 8.62(d, J = 8.8 Hz, 1H),
8.36–8.29 (m, 3H), 7.77–7.68 (m, 4H), 7.53 (d, J = 8.8 Hz,
2H) ppm; 13C NMR (100 MHz, CDCl3): d = 161.14, 144.98,
137.00, 135.59, 130.55, 129.43, 129.14, 128.96, 128.85,
128.33, 127.37, 127.19, 126.43, 126.14, 123.71, 123.34,
ꢀ
ꢀ
120.81 ppm; IR (KBr): m = 3055, 2910, 1617, 1548,
122.87, 121.11, 120.76 ppm; IR (KBr): m = 3055, 2921,
1601, 1479,1451, 1308, 1235, 1094, 1084, 1030, 831, 757,
1487, 1315, 1058, 755, 722, 692, 685, 539 cm-1; MS
(ESI): m/z = 295 (M?, 100).
722, 683, 544 cm-1; MS (ESI): m/z = 329 (M?, 100).
2-(p-Tolyl)phenanthro[9,10-d][1,3]oxazole
2-(4-Nitrophenyl)phenanthro[9,10-d][1,3]oxazole
(2f, C21H12N2O3)
(2b, C22H15NO)
Yellow crystals; 56 % yield; m.p.: 241–243 °C; Rf = 0.66
(hexan/diethyl ether 9/1); 1H NMR (400 MHz, CDCl3):
d = 8.73 (app. t, J = 17.6 Hz, 2H), 8.64 (d, J = 8.0 Hz,
1H), 8.33 (d, J = 7.6 Hz, 1H), 8.27 (d, J = 8.0 Hz, 2H), 7.78–
Yellow crystals; 62 % yield; m.p.: 252–254 °C; Rf = 0.52
(hexan/diethyl ether 9/1); 1H NMR (400 MHz, CDCl3):
d = 8.77 (q, J = 19.6 Hz, 2H), 8.64 (m, J = 10.0 Hz, 1H),
8.55 (q, J = 8.8 Hz, 2H), 8.43 (q, J = 9.2 Hz, 2H), 8.38 (d,
J = 10 Hz, 1H), 7.72–7.81 (m, 4H) ppm; 13C NMR
(100 MHz, CDCl3): d = 160.01, 149.17, 133.29, 130.28,
129.39, 128.02, 127.80, 127.46, 126.95, 126.18, 124.55,
124.17, 123.81, 123.22, 121.39, 121.11, 121.02 ppm; IR
7.61 (m, 4H), 7.37 (d, J = 8.0 Hz, 2H), 2.47 (s, 3H) ppm; 13
C
NMR (100 MHz, CDCl3): d = 162.42, 141.16, 135.58,
129.50, 129.20, 128.88, 127.23, 127.11, 126.29, 126.10,
125.92, 124.96, 123.64, 123.29, 122.91, 121.16, 120.72,
ꢀ
ꢀ
21.45 ppm; IR (KBr): m = 3027, 2912, 1613, 1496, 1311,
(KBr): m = 3064, 2962, 1606, 1511,1338, 1104, 853, 744,
1061, 822, 755, 725, 691, 497 cm-1; MS (ESI): m/z = 309
710, 668 cm-1; MS (ESI): m/z = 340 (M?, 100).
(M?, 100).
Acknowledgments This work was supported by a grant from The
Hungarian Research Fund (OTKA) #K108489 and COST Actions
CM1205, CM1201, and CM1003.
2-(4-Methoxyphenyl)phenanthro[9,10-d][1,3]oxazole
(2c, C22H15NO2)
Yellow crystals; 37 % yield; m.p.: 219–223 °C; Rf = 0.33
(hexan/diethyl ether 9/1); 1H NMR (400 MHz, CDCl3):
d = 8.73 (app. t, J = 16.4 Hz, 2H), 8.63 (d, J = 9.2 Hz,
1H), 8.32–8.29 (m, 3H), 7.76–7.64 (m, 4H), 7.07 (d,
J = 9.2 Hz, 2H), 3.91 (s, 3H) ppm; 13C NMR (100 MHz,
CDCl3): d = 162.31, 144.52, 135.60, 129.06, 128.84,
127.18, 127.05, 126.27, 125.97, 125.85, 123.63, 123.28,
122.88, 121.16, 120.62, 120.38, 114.33, 55.33 ppm; IR
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ꢀ
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Brown crystals; 19 % yield; m.p.: 220–222 °C; Rf = 0.21
(hexan/diethyl ether 9/1); 1H NMR (400 MHz, CDCl3):
d = 8.75 (app. t, J = 14.8 Hz, 2H), 8.64 (d, J = 9.2 Hz,
1H), 8.33 (d, J = 8.8 Hz, 1H), 8.24 (d, J = 8.8 Hz, 2H),
7.76–7.63 (m, 4H), 6.83 (d, J = 9.2 Hz, 2H), 3.09 (s, 6H)
ppm; 13C NMR (100 MHz, CDCl3): d = 163.56, 152.11,
144.37, 129.02, 128.93, 127.46, 127.36, 126.36, 126.07,
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´ ´ ´
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ꢀ
40.55 ppm; IR (KBr): m = 3051, 2896, 2851, 2794, 1611,
1502,1443, 1362, 1233, 1188, 1166, 1058, 814, 755, 737,
´
14. Cossıo FP, Alonso C, Lecea B, Ayerbe M, Rubiales G, Palacios
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721 cm-1; MS (ESI): m/z = 338 (M?, 100).
123