Jan-Feb 2006
Reaction of 3-Aminoquinoline-2,4-diones with Isocyanates
209
This compound was prepared as colourless crystals, 199 mg
(57%), mp 178-184 °C (ethyl acetate); ir: ν 3411, 3325, 3192,
3062, 2930, 2872, 1672, 1698, 1493, 1448, 1415, 1378, 1225,
3082, 2957, 2931, 2872, 1691, 1678, 1602, 1497, 1465, 1438,
1421, 1376, 1363, 1334, 1314, 1212, 1165, 1125, 1080, 1062,
1041, 999, 937, 858, 807, 775, 767, 671, 615, 546, 533 cm ; pos-
-1
-1
1138, 1076, 753, 703, 683, 601 cm ; positive-ion APCI-ms: m/z
itive-ion APCI-ms and ms/ms of m/z 388 are the same: m/z 388
+
+
+
+
+
352 [M+H] , 334 [M+H-H O] , 308 [M+H-NH CO] , 279
[M+H] (100% for MS), 370 [M+H-H O] , 344 [M+H-
2
2
2
+
+
-
[M+H-CH CH CH CH NH ] , 253 [M+H-CH CH CH CH -
NCO] (100%), 236 [M+H-CH CH CH CH NCO-NH ] , 209
[M+H-CH CH CH CH NCO-NH -HCN] ; positive-ion APCI-
ms/ms of m/z 352: m/z 253 [M+H-CH CH CH CH NCO]
(100%), 236 [M+H-CH CH CH CH NCO-NH ] ; negative-ion
APCI-ms: m/z 350 [M-H] (100%), 332 [M-H-H O] , 251 [M-H-
NH CO] , 314 [M-H-H O-butene] , 289 [M+H-CH CH -
2 2 3 2
3
2
2
2
2
3
2
2
2
+
+
+
CH CH NCO] (100% for ms/ms); negative-ion APCI-ms: m/z
3
2
2
2
3
2 2
+
-
-
-
386 [M-H] (100%), 368 [M-H-H O] , 357 [M-H-HCO] , 312
2
3
2
2
2
3
+
-
-
[M-H-H O-butene] , 287 [M-H-CH CH CH CH NCO] ; nega-
3
2
2
2
2 3 2 2 2
+
tive-ion APCI-ms/ms of m/z 386: m/z 287 [M-H-
3
2
2
2
3
-
-
-
CH CH CH CH NCO] (100%).
2
3
2
2
2
-
CH CH CH CH NCO] , 207 [M-H-CH CH CH CH NCO-
Anal. Calcd. for C
H N O : C, 68.19; H, 8.58; N, 10.84.
3
2
2
2
3
2
2
2
22 33 3 3
-
NH -HCN] ; negative-ion APCI-ms/ms of m/z 350: m/z 332 [M-
H-H O] , 306 [M-H-NH CO] , 277 [M-H-CH CH CH CH -
NH ] , 251 [M-H-CH CH CH CH NCO] , 234 [M-H-
Found: C, 68.41; H, 8.65; N, 10.93.
3
-
-
2
2
3
2
2
2
3,3a-Dibutyl-1-phenyl-9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imi-
dazo[4,5-c]quinoline-2,4-dione (7dy).
-
-
2
3
2
2
2
-
CH CH CH CH NCO-NH ] (100%), 207 [M-H-CH CH CH -
3
2
2
2
3
3
2
2
-
CH NCO-NH -HCN] .
This compound was prepared as colourless crystals, 349 mg
(86%), mp 147-153 °C (chloroform); ir: ν 3403, 3204, 3116,
3082, 2959, 2933, 2873, 1696, 1678, 1617, 1601, 1542, 1493,
1446, 1415, 1376, 1310, 1218, 1178, 1127, 1096, 1081, 1038,
2
3
Anal. Calcd. for C
H N O : C, 68.36; H, 6.02; N, 11.96.
20 21 3 3
Found: C, 68.07; H, 6.15; N, 11.78.
1,3a-Dibutyl-3-methyl-9b-hydroxy-3,3a,5,9b-tetrahydro-1H-
imidazo[4,5-c]quinoline-2,4-dione (7cx).
-1
998, 802, 755, 701, 692, 669, 655, 631, 577, 558, 506 cm ; pos-
+
+
itive-ion APCI-ms: m/z 408 [M+H] (100%), 390 [M+H-H O] ,
2
+
+
This compound was prepared as colourless crystals, 283 mg
(82%), mp 122-140 °C (ethyl acetate); ir: ν 3211, 3078, 2957,
2931, 2859, 1690, 1676, 1619, 1600, 1493, 1453, 1431, 1401,
1377, 1214, 1125, 1081, 1042, 999, 937, 837, 761, 674, 658, 648,
364 [M+H-NH CO] , 289 [M+H-C H NCO] ; positive-ion
APCI-ms/ms of m/z 408: m/z 289 [M+H-C H NCO] (100%),
271 [M+H-C H NCO-H O] ; negative-ion APCI-ms: m/z 406
[M-H] (100%), 377 [M-H-HCO] , 332 [M-H-H O-butene] , 287
[M-H-C H NCO] , 269 [M-H-C H NCO-H O] ; negative-ion
APCI-ms/ms of m/z 406: m/z 287 [M-H-C H NCO] (100%).
2
6 5
+
6
5
+
6
5
2
-
-
-
2
-1
+
-
-
628, 571, 541 cm ; positive-ion APCI-ms: m/z 346 [M+H] , 328
6
5
6
5
2
+
+
-
[M+H-H O] (100%), 302 [M+H-NH CO] , 247 [M+H-
2
2
6
5
+
CH CH CH CH NCO] ; positive-ion APCI-ms/ms of m/z 346:
Anal. Calcd. for C
H N O : C, 70.74; H, 7.17; N, 10.31.
3
2
2
2
24 29 3 3
+
m/z 247 [M+H-CH CH CH CH NCO] (100%), 191 [M+H-
Found: C, 70.61, H, 7.31, N, 10.38.
3
2
2
2
+
+
CH CH CH CH NCO-butene] , 146 [C H NHCOCHCH ] ;
3
2
2
2
6
4
2
3-Benzyl-1,3a-dibutyl-9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imi-
dazo[4,5-c]quinoline-2,4-dione (7ex).
-
negative-ion APCI-ms: m/z 344 [M-H] (100%), 315 [M-H-
HCO] , 270 [M-H-H O-butene] , 245 [M-H-CH CH CH -
CH NCO] ; negative-ion APCI-ms/ms of m/z 344: m/z 245 [M-
H-CH CH CH CH NCO] (100%), 188 [M-H-CH CH CH -
-.
-
2
3
2
2
-
This compound was prepared as colourless crystals, 381 mg
(90%), mp 99-105 °C (hexane); ir: ν 3363, 3242, 3226, 3084,
3034, 2932, 2872, 1689, 1618, 1601, 1494, 1451, 1417, 1377,
1360, 1316, 1217, 1123, 1077, 1041, 1018, 939, 849, 759, 732,
2
-
3
2
2
2
3
2
2
-
CH NCO-butyl] .
2
Anal. Calcd. for C
H N O : C, 66.06; H, 7.88; N, 12.16.
19 27 3 3
-1
701, 670, 655, 625, 617, 545, 531 cm ; positive-ion APCI-ms:
Found: C, 65.83; H, 8.03; N, 12.32.
+
+
m/z 422 [M+H] (100%), 404 [M+H-H O] , 378 [M+H-
2
3a-Butyl-3-methyl-1-phenyl-9b-hydroxy-3,3a,5,9b-tetrahydro-
1H-imidazo[4,5-c]quinoline-2,4-dione (7cy).
+.
+
NH CO]
,
348 [M+H-H O-butene] , 323 [M+H-
2
2
+
CH CH CH CH NCO] ; positive-ion APCI-ms/ms of m/z 422:
3
2
2
2
+
+
This compound was prepared as colourless crystals, 228 mg
(62%), mp 168-174 °C (ethyl acetate); ir: ν 3391, 3198, 3064,
2959, 2930, 2864, 1674, 1601, 1495, 1449, 1394, 1367, 1219,
1156, 1126, 1091, 1069, 1043, 1006, 970, 915, 853, 758, 704,
m/z 404 [M+H-H O] , 344 [M+H-C H ] , 323 [M+H-
2
6
6
+
CH CH CH CH NCO] (100%), 305 [M+H-CH CH -
3
2
2
2
3
2
+
CH CH NCO-H O] , 245 [M+H-CH CH CH CH NCO-
2
2
2
3
2
2
2
+
+
C H ] , 164 [C H CH NH CH CH CH CH ] ; negative-ion
APCI-ms: m/z 420 [M-H] (100%), 402 [M-H-H O] , 391 [M-H-
HCO] , 346 [M-H-H O-butene] , 321 [M-H-CH CH -
CH CH NCO] ; negative-ion APCI-ms/ms of m/z 420: m/z 402 [M-
H-H O] , 321 [M-H-CH CH CH CH NCO] (100%), 303 [M-H-
CH CH CH CH NCO-H O] , 230 [M-H-CH CH CH CH NCO-
6
6
6
5
2
2
2
2
2
3
-1
-
-
672, 652, 634, 541, 508 cm ; positive-ion APCI-ms: m/z 366
2
+
+
+
-.
-
[M+H] (100%), 348 [M+H-H O] , 322 [M+H-NH CO] , 247
2
2
2
3
2
+
-
[M+H-C H NCO] ; positive-ion APCI-ms/ms of m/z 366: m/z
247 [M+H-C H NCO] (100%), 229 [M+H-C H NCO-H O] ,
6
5
2
2
+
+
-
-
6
5
6
5
2
2
3
2
2
2
+
-
146 [C H NHCOCHCH ] ; negative-ion APCI-ms: m/z 364 [M-
6
4
2
3
2
2
2
2
3
2
2
2
-
-
-
-
-
H] , 346 [M-H-H O] , 290 [M-H-H O-butene] , 245 [M-H-
C H NCO] (100%), 188 [M-H-C H NCO-butyl] ; negative-ion
APCI-ms/ms of m/z 364: m/z 245 [M-H-C H NCO] (100%),
188 [M-H-C H NCO-butyl] .
C H CH ] , 216 [C H NHCOC(butyl)CO] .
2
2
6
5
2
6 4
-
-
Anal. Calcd. for C
H N O : C, 71.23; H, 7.41; N, 9.97.
6
5
6 5
25 31 3 3
-
Found: C, 71.45; H, 7.57; N, 10.08.
6
5
-
6
5
3-Benzyl-3a-butyl-1-phenyl-9b-hydroxy-3,3a,5,9b-tetrahydro-
1H-imidazo[4,5-c]quinoline-2,4-dione (7ey).
Anal. Calcd. for C
H N O : C, 69.02; H, 6.34; N, 11.50.
21 23 3 3
Found: C, 69.11; H, 6.48; N, 11.42.
This compound was prepared as colourless crystals, 421 mg
(95%), mp 152-163 °C (cyclohexane); ir: ν 3356, 3214, 3064,
2959, 2928, 2871, 1690, 1617, 1601, 1496, 1440, 1411, 1364,
1157, 1125, 1072, 1042, 1025, 954, 919, 865, 831, 756, 731, 697,
1,3,3a-Tributyl-9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imi-
dazo[4,5-c]quinoline-2,4-dione (7dx).
This compound was prepared as colourless crystals, 237 mg
(61%), mp 126-142 °C (chloroform); ir: ν 3336, 3344, 3207,
-1
670, 655, 616, 600, 551, 507, 491 cm ; positive-ion APCI-ms: