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Russ.Chem.Bull., Int.Ed., Vol. 52, No. 1, January, 2003
Kravchenko et al.
Table 2 (continued)
Compound
IR,
ν/сm–1
1H NMR (DMSOꢀd6),
MS,
m/z (Irel (%))
δ (J/Hz)
214 [М+ – 0.5 Н2О] (3),
171 (9), 153 (38), 125 (38),
112 (38), 99 (63), 84 (66),
70 (22), 59 (10), 55 (100)
ꢀ
2.50 (m, 2 Н, СН2СО);
(1R*,5S*)ꢀ3ꢀ(3,7ꢀDioxoꢀ
2,4,6,8ꢀtetraazabiꢀ
cyclo[3.3.0]octꢀ2ꢀ
yl)propanoic acid
(1b)
608, 672, 708, 736, 752,
768, 800, 808, 848, 884,
3.22, 3.42 (both m, 2 H, NСН2);
3
896, 920, 976, 1056, 1068,
1096, 1120, 1132, 1156, 1204,
1228, 1252, 1296, 1328, 1344,
1360, 1400, 1408, 1416, 1440,
1460, 1500, 1552, 1664, 1684,
1700, 1720, 2568, 2640, 2936,
3000, 3304, 3600, 3640
5.19 (d, 1 Н, С(5)H, J = 8.2);
3
5.29 (d, 1 Н, С(1)H, J = 8.2);
7.29, 7.34, 7.38
(all br.s, 1 H each, 3 NH);
12.30 (br.s, 1 H, COOH)
(1R*,5S*)ꢀ4ꢀ(3,7ꢀDioxoꢀ
2,4,6,8ꢀtetraazabiꢀ
cyclo[3.3.0]octꢀ2ꢀ
yl)butanoic acid
(1c)
664, 720, 736, 796, 816, 840,
888, 908, 928, 976, 1008,
1.67 (m, 2 Н, ССH2C);
2.17 (t, 2 H, CH2CO, J = 7.5);
—
3
1020, 1068, 1080, 1112, 1156,
1196, 1208, 1224, 1232, 1252,
1272, 1284, 1296, 1304, 1320,
1328, 1336, 1352, 1392, 1508,
1564, 1680, 1690, 1712, 1720,
2656, 2736, 2944, 2944, 3008,
3264, 3384, 3456
2.97, 3.17 (both m, 1 H each,
NCH2); 5.19, 5.25 (both d,
1 H each, CHCH, 3J = 8.3);
7.28, 7.30, 7.41
(all s, 1 H each, 3 NH);
12.06 (br.s, 1 Н, COOH)
(1R*,5S*)ꢀ5ꢀ(3,7ꢀDioxoꢀ
2,4,6,8ꢀtetraazabiꢀ
cyclo[3.3.0]octꢀ2ꢀ
yl)pentanoic acid
(1d)
664, 712, 736, 752, 760, 800,
816, 848, 888, 964, 1076, 1088, 2.22 (br.s, 2 Н, CH2CO); 2.94,
1120, 1152, 1208, 1220, 1256,
1296, 1348, 1376, 1408, 1424,
1504, 1564, 1692, 2840, 2860,
2980, 2952, 3000, 3210, 3248
1.44 (br.s, 4 Н, C(CH2)2C);
—
—
3.16 (both br.s, 1 H each, NCH2);
5.19 (br.m, 2 Н, CHCH);
7.25 (br.s, 2 Н, 2 NH);
7.41 (s, 1 Н, NH);
12.00 (br.s, 1 Н, COOH)
(1R*,5S*)ꢀNꢀ[(3,7ꢀDioxoꢀ
2,4,6,8ꢀtetraazabiꢀ
cyclo[3.3.0]octꢀ2ꢀ
yl)acetyl]aminoꢀ
ethanoic acid
612, 624, 648, 668, 688, 724,
740, 752, 768, 796, 816, 848,
880, 888, 904, 924, 944, 960,
992, 1024, 1052, 1068, 1116,
1164, 1248, 1288, 1296, 1312,
1336, 1352, 1368, 1384, 1400,
1416, 1432, 1440, 1496, 1500,
1520, 1540, 1580, 1664, 1672,
1704, 1720, 1728, 1740, 2544,
2696, 2928, 2952, 3008, 3296,
3368, 3392
3.53, 3.96 (both d, 1 H each, NCH2,
2J = 17.2); 3.77 (d, 2 Н, NHCH2,
3J = 5.6); 5.33, 5.38 (both d, 2 Н,
CHCH, 3J = 8.3); 7.32 (br.s, 2 Н,
2 NH); 7.52 (s, 1 Н, NH);
8.30 (t, 1 H, NHCH2, 3J = 5.6);
12.70 (br.s, 1 Н, COOH)
(1e)
(1R*,5S*)ꢀ2ꢀ(2ꢀHydroxyꢀ
ethyl)ꢀ2,4,6,8ꢀtetraazaꢀ
bicyclo[3.3.0]octaneꢀ
3,7ꢀdione
684, 716, 736, 784, 792, 844,
864, 876, 888, 928, 1016, 1032, 3.45 (m, 2 Н, СН2O);
3.03, 3.21 (both m, 2 Н, NСН2);
186 [М]+ (2), 156 (82),
155 (70), 143 (13), 126 (6),
113 (20), 112 (100), 100 (20),
98 (6), 84 (56), 83 (63),
82 (20), 71 (16), 69 (57),
58 (80), 56 (58)
1064, 1084, 1112, 1168, 1248,
1256, 1264, 1288, 1344, 1360,
1368, 1388, 1500, 1560, 1680,
1712, 1732, 2928, 2992, 3280,
3392, 3416
4.75 (t, 1 H, OH, 3J = 5.2);
3
5.19 (d, 1 H, C(5)H, J = 8.2);
(1f)
5.30 (d, 1 Н, С(1)H, 3J = 8.2);
7.29 (br.m, 3 H, 3 NH)
(1R*,5S*)ꢀ2ꢀ[2ꢀHydroxyꢀ
(1,1ꢀdimethyl)ethyl]ꢀ
2,4,6,8ꢀtetraazabiꢀ
cyclo[3.3.0]octaneꢀ
3,7ꢀdione
720, 748, 764, 860, 888, 928,
1016, 1028, 1064, 1080, 1112,
1160, 1184, 1208, 1260, 1312,
1348, 1384, 1498, 1560, 1664,
1676, 1692, 2928, 2960,
3008, 3240
1.22, 1.24 (both s, 3 H each, 2 Me);
3.34, 3.62 (both dd, 1 H each, СН2,
2J = 10.7, 3J = 4.2); 4.89 (br.t,
—
3
1 Н, ОН, J = 4.2); 5.11 (d, 1 Н,
С(5)H, 3J = 8.2); 5.46 (d, 1 Н,
3
(1g)
С(1)H, J = 8.2); 7.17 (br.s, 1 Н,
NH); 7.26 (br.s, 2 H, 2 NH)
1
The signals overlap with the signal of the solvent; because of this, the H NMR spectrum in D2O and the 13C NMR spectrum were
ꢀ
1
additionally recorded. H NMR (D2O), δ: 2.14 (t, 2 H, CH2CO, J = 6.7 Hz); 2.82—2.12 (m, 2 H, NCH2); 5.02 and 5.10 (both d,
1 H each, CHCH, 3J = 8.5 Hz). 13C NMR, δ: 32.7, 36.7 (2 CH2); 62.4, 68.1 (2 CH); 159.2, 161.3 (2 CO); 173.1 (COOH).