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Helvetica Chimica Acta – Vol. 94 (2011)
91 (16), 77 (40), 64 (13), 63 (6), 51 (11). Anal. calc. for C28H20N2O4 (448.47): C 74.99, H 4.50, N 6.25;
found: C 74.78, H 4.71, N 6.08.
1,3a-Dibutyl-5,9b-dihydro-9b-hydroxy[1,3]oxazolo[5,4-c]quinoline-2,4(1H,3aH)-dione (3a). Pre-
pared from 1a and BuNCO (besides 2a). Colorless crystals. M.p. 174 – 1908 (hexane/AcOEt). IR:
3322, 3208, 3083, 2963, 2930, 2874, 1745, 1687, 1601, 1496, 1468, 1447, 1407, 1380, 1319, 1251, 1221, 1195,
1158, 1131, 1085, 1063, 1044, 1025, 1003, 936, 849, 763, 734, 677, 629, 581, 546. 1H- and 13C-NMR: Table 3.
EI-MS: 332 (Mþ, 10), 234 (8), 233 (27), 216 (11), 215 (9), 190 (36), 188 (7), 186 (10), 178 (12), 177 (100),
175 (10), 174 (12), 163 (8), 162 (24), 150 (5), 149 (54), 148 (33), 146 (16), 144 (5), 132 (8), 130 (6), 128
(7), 126 (5), 120 (31), 119 (10), 112 (5), 104 (6), 103 (5), 100 (5), 98 (6), 97 (8), 95 (5), 93 (11), 92 (23),
91 (6), 90 (7), 86 (5), 85 (15), 83 (10), 81 (5), 77 (10), 74 (17), 72 (28), 71 (10), 70 (7), 69 (18), 67 (8), 65
(16), 64 (5), 60 (8), 59 (49), 57 (65), 56 (18), 55 (52), 54 (5). Anal. calc. for C18H24N2O4 (332.39): C 65.04,
H 7.28, N 8.43; found: C 65.08, H 7.31, N 8.44.
1-Butyl-5,9b-dihydro-9b-hydroxy-3a-phenyl[1,3]oxazolo[5,4-c]quinoline-2,4(1H,3aH)-dione (3c).
Prepared from 1c and BuNCO (besides 2c and 7). Colorless crystals. M.p. 215 – 2208 (EtOH). IR:
3397, 3197, 3064, 2958, 2933, 2876, 1763, 1685, 1620, 1600, 1495, 1449, 1411, 1393, 1377, 1312, 1253, 1224,
1
1175, 1159, 1141, 1102, 1068, 1051, 1032, 990, 942, 900, 863, 753, 707, 680, 657, 604, 563, 535. H- and
13C-NMR: Table 3. EI-MS: 352 (Mþ, 2), 253 (44), 236 (5), 148 (14), 120 (6), 106 (8), 105 (100), 92 (7), 77
(24), 56 (8), 43 (10), 41 (14). Anal. calc. for C20H20N2O4 (352.38): C 68.17, H 5.72, N 7.95; found C 68.27,
H 5.78, N 8.06.
1,3a-Dibutyl-5,9b-dihydro-9b-hydroxy-5-methyl[1,3]oxazolo[5,4-c]quinoline-2,4(1H,3aH)-dione
(3e). Prepared from 1e and BuNCO (besides 2e). Colorless crystals. M.p. 137 – 1408 (benzene/hexane).
IR: 3297, 2950, 2928, 2870, 1745, 1685, 1605, 1473, 1393, 1366, 1346, 1299, 1271, 1217, 1196, 1173, 1123,
1096, 1069, 1052, 1032, 986, 946, 900, 817, 794, 770, 674, 652, 584, 541. 1H- and 13C-NMR: Table 3. EI-MS:
346 (Mþ, 8), 230 (6), 192 (7), 191 (57), 177 (5), 176 (9), 163 (19), 162 (18), 160 (5), 149 (22), 146 (6), 134
(16), 128 (6), 126 (12), 125 (5), 114 (11), 113 (5), 112 (11), 111 (9), 109 (7), 106 (8), 105 (6), 104 (13),
100 (6), 99 (9), 98 (11), 97 (18), 96 (8), 95 (12), 91 (5), 86 (9), 85 (20), 84 (8), 83 (21), 85 (7), 81 (12), 79
(6), 77 (9), 74 (51), 73 (6), 72 (57), 71 (28), 70 (13), 69 (38), 68 (7), 67 (17), 60 (18), 59 (100), 58 (5), 57
(6), 56 (22), 55 (73), 54 (8). Anal. calc. for C19H26N2O4 (346.42): C 65.87, H 7.56, N 8.09; found: C 66.15,
H 7.62, N 8.14.
1-Butyl-5,9b-dihydro-9b-hydroxy-5-methyl-3a-phenyl[1,3]oxazolo[5,4-c]quinoline-2,4(1 H,3aH)-di-
one (3g). Prepared from 1g and BuNCO. Colorless crystals. M.p. 188 – 1938 (benzene). IR: 3381, 2962,
2932, 2870, 1757, 1684, 1605, 1474, 1387, 1364, 1326, 1269, 1227, 1178, 1137, 1070, 1056, 1046, 1017, 975, 944,
861, 834, 765, 755, 724, 699, 654, 593, 530. 1H- and 13C-NMR: Table 3. EI-MS: 366 (Mþ, 15), 267 (12), 251
(8), 250 (21), 237 (6), 234 (6), 233 (39), 223 (8), 222 (8), 177 (19), 162 (25), 149 (5), 134 (13), 116 (6),
106 (12), 105 (100), 104 (10), 91 (7), 79 (5), 78 (8), 77 (48), 71 (5), 57 (16), 56 (8), 55 (7), 51 (8). Anal.
calc. for C21H22N2O4 (366.41): C 68.84, H 6.05, N 7.65; found: C 68.75, H 6.05, N 7.62.
1,3a-Dibutyl-5,9b-dihydro-9b-hydroxy-5-phenyl[1,3]oxazolo[5,4-c]quinoline-2,4(1H,3aH)-dione
(3i). Prepared from 1i and BuNCO (besides 2i). Colorless crystals. M.p. 171 – 1748 (benzene/hexane).
IR: 3357, 3065, 2962, 2934, 2864, 1751, 1687, 1606, 1593, 1499, 1465, 1395, 1350, 1339, 1300, 1268, 1229,
1206, 1186, 1170, 1148, 1131, 1090, 1055, 1031, 961, 945, 911, 825, 767, 735, 705, 655, 627, 611, 589, 517. 1H-
and 13C-NMR: Table 3. EI-MS: 409 (5), 408 (Mþ, 15), 309 (10), 292 (5), 262 (7), 254 (17), 253 (100), 252
(7), 251 (6), 250 (7), 239 (7), 238 (7), 226 (10), 225 (68), 224 (25), 222 (5), 197 (8), 196 (53), 195 (12),
180 (6), 169 (5), 168 (11), 167 (21), 166 (7), 139 (5), 119 (8), 105 (5), 92 (8), 77 (22), 57 (26), 56 (19), 55
(8), 51 (13). Anal. calc. for C24H28N2O4 (408.49): C 70.57, H 6.91, N 6.86; found: C 70.68, H 6.92, N 6.79.
1-Butyl-5,9b-dihydro-9b-hydroxy-3a,5-diphenyl[1,3]oxazolo[5,4-c]quinoline-2,4(1H,3aH)-dione
(3k). Prepared from 1k and BuNCO (besides 2k). Colorless crystals. M.p. 229 – 2368 (AcOEt). IR: 3371,
3075, 2960, 2932, 2857, 1755, 1702, 1604, 1591, 1497, 1489, 1464, 1389, 1348, 1299, 1263, 1224, 1140, 1104,
1067, 1048, 1008, 942, 926, 890, 833, 757, 705, 653, 607, 522. 1H- and 13C-NMR: Table 3. EI-MS: 429 (5),
428 (Mþ, 17), 330 (8), 329 (36), 313 (6), 312 (11), 295 (8), 285 (5), 284 (5), 239 (5), 225 (6), 224 (38), 196
(24), 195 (7), 167 (9), 106 (9), 105 (100), 77 (28), 51 (5), 43 (5), 41 (9). Anal. calc. for C26H24N2O4
(428.48): C 72.88, H 5.65, N 6.54; found: C 72.68, H 5.71, N 6.48.
3-Phenylquinazoline-2,4(1H,3H)-dione (4). Prepared from 1a and PhNCO (besides 2b). Colorless
crystals. M.p. 282 – 2848 (AcOEt; 280 – 2818 [13]). IR: identical to that published in [17]. 1H-NMR