TABLE 4. 1H NMR Spectra of the Quinazoline-2,4-diones 2, 3, 10, and 11
Com-
pound
Chemical shifts, δ, ppm (J, Hz)
2a
10.46 (1Н, br. s, NH+); 8.05 (1Н, dd, J = 7.8 and J = 1.6, H-5);
7.80 (1H, td, J = 7.9 and J = 1.6, H-7); 7.47 (1Н, d, J = 8.4, Н-8);
7.31 (1Н, t, J = 7.6, Н-6); 4.28 (2Н, t, J = 7.0, NCH2); 3.51 (3Н, s, СН3);
3.22 (6Н, m, N(CH2)3); 1.23 (6Н, t, J = 7.5, 2СН3)
2b
10.68 (1Н, br. s, NH+); 8.05 (1Н, dd, J = 7.8 and J = 1.4, H-5);
7.78 (1H, td, J = 7.9 and J = 1.6, H-7); 7.51 (1Н, d, J = 8.4, Н-8);
7.30 (1Н, t, J = 7.5, Н-6); 4.27 (2Н, t, J = 7.1, NCH2СН2N);
4.13 (2Н, q, J = 7.2, NCH2СН3); 3.21 (6Н, m, N(CH2)3);
1.23 (9Н, m, 1-NCH2СН3 + 2СН3)
2c
10.07 (1Н, br. s, NH+); 8.06 (1Н, dd, J = 7.9 and J = 1.4, H-5);
7.78 (1H, td, J = 7.9 and J = 1.6, H-7); 7.52 (1Н, d, J = 8.6, Н-8);
7.30 (1Н, t, J = 7.5, Н-6); 4.27 (2Н, t, J = 6.9, NCH2СН2N);
4.04 (2Н, t, J = 7.6, NCH2С2Н5); 3.22 (6Н, m, N(CH2)3); 1.64 (2Н, m, NCH2СН2СН3);
1.21 (6Н, t, J = 7.1, 2СН3); 0.94 (3Н, t, J = 7.5, NCH2СН2СН3)
2d
10.24 (1Н, br. s, NH+); 8.06 (1Н, dd, J = 7.9 and J = 1.6, H-5);
7.78 (1H, td, J = 7.8 and J = 1.6, H-7); 7.50 (1Н, d, J = 8.5, Н-8);
7.30 (1Н, t, J = 7.5, Н-6); 4.27 (2Н, t, J = 6.9, NCH2СН2N);
4.08 (2Н, t, J = 7.6, NCH2С3Н7); 3.23 (6Н, m, N(CH2)3); 1.60 (2Н, q, J = 7.4, СН2С2Н5);
1.39 (2Н, m, NCH2СН2СН2СН3); 1.22 (6Н, t, J = 7.1, 2СН3);
0.91 (3Н, t, J = 7.2, NСН2CH2СН2СН3)
2e
10.36 (1Н, br. s, NH+); 8.06 (1Н, dd, J = 7.8 and J = 1.7, H-5);
7.77 (1H, td, J = 7.8 and J = 1.6, H-7); 7.49 (1Н, d, J = 8.3, Н-8);
7.29 (1Н, t, J = 7.5, Н-6); 4.28 (2Н, t, J = 6.9, NCH2СН2N);
3.95 (2Н, d, J = 7.3, NCH2СН(СН3)2); 3.21 (6Н, m, N(CH2)3); 2.08 (1Н, m, СН(СН3)2);
1.21 (6Н, t, J = 7.2, 2СН3); 0.92 (6Н, d, J = 6.5, NCH2СН(СН3)2)
3
10.67 (1Н, br. s, NH+); 8.06 (1Н, d, J = 7.8, H-5); 7.76 (1H, t, J = 7.8, H-7);
7.49 (1Н, d, J = 8.5, Н-8); 7.30 (1Н, t, J = 7.4, Н-6); 4.31 (2Н, t, J = 6.8, NCH2СН2N);
3.95 (2Н, d, J = 7.4, NCH2СН(СН3)2); 3.77–3.04 (10Н, m, N(CH2)3 + О(СН2)2);
2.09 (1Н, m, СН(СН3)2); 0.92 (6Н, d, J = 6.5, NCH2СН(СН3)2)
10b
10c
10d
10e
8.04 (1Н, dd, J = 8.0 and J = 1.6, H-5); 7.75 (1H, td, J = 7.8 and J = 2.0, H-7);
7.47 (1H, d, J = 8.5, H-8); 7.26 (1H, t, J = 7.6, H-6); 4.76 (1Н, t, J = 5.8, ОН);
4.12 (2Н, q, J = 7.1, NCH2СН3); 4.02 (2Н, t, J = 6.4, NCH2СН2ОН);
3.54 (2Н, q, J = 6.4, СН2ОН); 1.19 (3Н, t, J = 7.1, СН3)
8.03 (1Н, dd, J = 8.1 and J = 1.6, H-5); 7.74 (1H, td, J = 7.9 and J = 2.0, H-7);
7.45 (1H, d, J = 8.2, H-8); 7.26 (1H, t, J = 7.5, H-6); 4.76 (1Н, t, J = 5.8, ОН);
4.03 (4Н, m, NCH2С2Н5 + NCH2СН2ОН); 3.54 (2Н, q, J = 6.5, СН2ОН);
1.61 (2Н, m, СН2СН3); 0.92 (3Н, t, J = 7.5, СН3)
8.04 (1Н, d, J = 7.9, H-5); 7.74 (1H, t, J = 7.8, H-7); 7.45 (1H, d, J = 8.3, H-8);
7.26 (1H, t, J = 7.6, H-6); 4.75 (1Н, t, J = 6.0, ОН);
4.04 (4Н, m, NCH2С3Н7 + NCH2СН2ОН); 3.54 (2Н, q, J = 6.2, СН2ОН);
1.55 (2Н, q, J = 7.2, СН2С2Н5); 1.36 (2Н, m, СН2СН3); 0.90 (3Н, t, J = 7.3, СН3)
8.04 (1Н, dd, J = 7.9 and J = 1.6, H-5); 7.73 (1H, td, J = 7.8 and J = 1.8, H-7);
7.45 (1H, d, J = 8.5, H-8); 7.25 (1H, t, J = 7.6, H-6); 4.75 (1Н, t, J = 5.9, ОН);
4.03 (2Н, t, J = 6.5, NCH2СН2ОН); 3.95 (2Н, d, J = 7.7, NCH2СН(СН3)2);
3.53 (2Н, q, J = 6.3, СН2ОН); 2.06 (1Н, m, СН(СН3)2); 0.89 (6Н, d, J = 6.8, 2СН3)
11b
11c
8.06 (1Н, dd, J = 7.8 and J = 1.6, H-5); 7.77 (1H, td, J = 7.9 and J = 1.6, H-7);
7.50 (1H, d, J = 8.4, H-8); 7.29 (1H, t, J = 7.6, H-6); 4.26 (2Н, t, J = 6.8, NCH2СН2Cl);
4.13 (2Н, q, J = 7.0, NCH2СН3); 3.79 (2Н, t, J = 6.8, СН2Cl); 1.19 (3Н, t, J = 7.0, СН3)
8.05 (1Н, dd, J = 7.9 and J = 1.6, H-5); 7.76 (1H, td, J = 7.9 and J = 1.6, H-7);
7.49 (1H, d, J = 8.5, H-8); 7.28 (1H, t, J = 7.6, H-6); 4.27 (2Н, t, J = 6.7, NCH2СН2Cl);
4.04 (2Н, t, J = 7.6, NCH2С2Н5); 3.79 (2Н, t, J = 6.7, СН2Cl); 1.62 (2Н, m, СН2СН3);
0.92 (3Н, t, J = 7.4, СН3)
11d
11e
8.05 (1Н, d, J = 7.9, H-5); 7.77 (1H, t, J = 7.8, H-7); 7.47 (1H, d, J = 8.5, H-8);
7.28 (1H, t, J = 7.5, H-6); 4.27 (2Н, t, J = 6.8, NCH2СН2Cl);
4.08 (2Н, t, J = 7.4, NCH2С3Н7); 3.79 (2Н, t, J = 6.8, СН2Cl);
1.58 (2Н, q, J = 7.2, СН2С2Н5); 1.35 (2Н, m, СН2СН3); 0.90 (3Н, t, J = 7.3, СН3)
8.06 (1Н, dd, J = 8.1 and J = 1.7, H-5); 7.76 (1H, td, J = 7.8 and J = 1.7, H-7);
7.48 (1H, d, J = 8.5, H-8); 7.29 (1H, t, J = 7.6, H-6); 4.28 (2Н, t, J = 6.6, NCH2СН2Cl);
3.96 (2Н, d, J = 7.3, NCH2СН(СН3)2); 3.80 (2Н, t, J = 6.6, СН2Cl);
2.07 (1Н, m, СН(СН3)2); 0.89 (6Н, d, J = 6.4, 2СН3)
101