TABLE 3. 1H NMR Spectra of Compounds 2-6
Com-
pound
Chemical shifts, , ppm (J, Hz)
7.81 (1H, d, J7,5 = 1.6, H-7); 7.69 (1H, dd, J5,7 = 1.6, J5,4 = 8.6, H-5);
7.05 (1H, d, J4,5 = 8.6, H-4); 3.39 (3H, s, 3-CH3)
2b
3а
3b
4a
9.15 (1H, s, NH); 7.83 (1H, d, J7,5 = 1.8, H-7); 7.72 (1H, dd, J5,7 = 1.8, J5,4 = 8.7, H-5);
7.01 (1H, d, J4,5 = 8.7, H-4)
7.80 (1H, d, J7,5 = 1.8, H-7); 7.71 (1H, dd, J5,7 = 1.8, J5,4 = 8.7, H-5);
7.02 (1H, d, J4,5 = 8.7, H-4); 3.38 (3H, s, 3-CH3)
9.16 (1H, s, NH); 7.82 (1H, d, J7,5 = 1.8, H-7); 7.69 (1H, dd, J5,7 = 1.8, J5,4 = 8.6, H-5);
7.01 (1H, d, J4,5 = 8.6, H-4); 2.48 (4H, q, J = 7.2, N(CH2CH3)2);
1.01 (6H, t, J = 7.2, N(CH2CH3)2)
9.15 (1H, s, NH); 7.83 (1H, d, J7,5 = 1.8, H-7); 7.68 (1H, dd, J5,7 = 1.8, J5,4 = 8.7, H-5);
7.02 (1H, d, J4,5 = 8.7, H-4); 3.02 (4H, m, N(CH2С3H7)2);
1.34-1.43 (4H, m, N(CH2CH2C2H5)2; 0.96-1.23 (4H, m, N(C2H4CH2CH3)2;
0.79-0.85 (6H, m, N(C3H6CH3)2)
4b
7.82 (1H, d, J7,5 = 1.8, H-7); 7.67 (1H, dd, J5,7 = 1.8, J5,4 = 8.6, H-5);
7.00 (1H, d, J4,5 = 8.6, H-4); 3.38 (3H, s, 3-CH3); 2.49 (4H, q, J = 7.2, N(CH2CH3)2);
1.02 (6H, t, J = 7.2, N(CH2CH3)2)
4c
7.83 (1H, d, J7,5 = 1.8, H-7); 7.67 (1H, dd, J5,7 = 1.8, J5,4 = 8.7, H-5);
7.01 (1H, d, J4,5 = 8.7, H-4); 3.38 (3H, s, 3-CH3); 3.03-3.21 (4H, m, N(CH2С3H7)2);
1.51-1.64 (4H, m, N(CH2CH2C2H5)2; 1.33–1.43 (4H, m, N(C2H4CH2CH3)2;
0.72-0.81 (6H, m, N(C3H6CH3)2)
4d
9.16 (1H, s, NH); 7.76 (1H, d, J7,5 = 1.8, H-7); 7.66 (1H, dd, J5,7 = 1.8, J5,4 = 8.8, H-5);
7.00 (1H, d, J4,5 = 8.8, H-4); 3.58 (4H, q, J = 6.9, N(CH2СН2)2СН2);
2.85 (4H, q, J = 6.9, N(СН2СН2)2СН2); 2.47 (2H, m, N(С2Н4)2CH2)
5a
9.14 (1H, s, NH); 7.78 (1H, d, J7,5 = 1.8, H-7); 7.67 (1H, dd, J5,7 = 1.8, J5,4 = 8.8, H-5);
7.04 (1H, d, J4,5 = 8.8, H-4); 3.59 (4H, t, J = 8.0, N(СН2)2); 2.84 (4H, t, J = 8.0, О(СН2)2)
5b
5c
7.77 (1H, d, J7,5 = 1.8, H-7); 7.68 (1H, dd, J5,7 = 1.8, J5,4 = 8.7, H-5);
7.03 (1H, d, J4,5 = 8.7, H-4); 3.59 (4H, t, J = 6.9, N(CH2СН2)2СН2);
3.38 (3H, s, 3-CH3); 2.82 (4H, t, J = 6.9, N(СН2СН2)2СН2); 2.44 (2H, m, N(С2Н4)2CH2)
7.78 (1H, d, J7,5 = 1.8, H-7); 7.66 (1H, dd, J5,7 = 1.8, J5,4 = 8.7, H-5);
5d
7.03 (1H, d, J4,5 = 8.7, H-4); 3.58 (4H, t, J = 8.0, N(СН2)2); 3.38 (3H, s, 3-CH3);
2.85 (4H, t, J = 8.0, О(СН2)2)
9.17 (1H, s, NH); 7.77 (1H, d, J7,5 = 1.8, H-7); 7.65 (1H, dd, J5,7 = 1.8, J5,4 = 8.8, H-5);
7.01 (1H, d, J4,5 = 8.8, H-4)
6a
6b
7.78 (1H, d, J7,5 = 1.8, H-7); 7.67 (1H, dd, J5,7 = 1.8, J5,4 = 8.8, H-5);
7.02 (1H, d, J4,5 = 8.8, H-4); 3.38 (3H, s, 3-CH3)
Mass spectra of the sulfamides 4,5 show, independent of the nature of the substituent R and the
character of the substituted amino groups, a uniform fragmentation with loss of the SO2–N(R1)2 to give
fragments A [M+-N(R1)2] and B [N(R1)2]. In the case of compounds 5a,c the molecular ion peak M+ has the
maximum intensity, whereas in compounds 4a-d and 5b,d the peak of fragment A has the greatest intensity
1
The H NMR spectra of compounds 2-6 (Table 3) contain characteristic signals of the protons of the
benzoxazoline fragment: a doublet of proton H-4 in the 7.00-7.05 ppm range (J4,5 = 8.6-8.8), a doublet of
doublets of proton H-5 at 7.65-7.72 (J5,4 = 8.6-8.8 and J5,7 1.6-1.9) and also a doublet for proton H-7 at 7.76-7.83
ppm (J7,5 = 1.6-1.8 Hz). Signals of the NH group appear at weak field (9.15-9.17) while the signals of the alkyl
groups of the amide appear at strong field (0.72-3.59 ppm).
EXPERIMENTAL
1
IR spectra of KBr tablets were recorded on a Perkin-Elmer model 2000 Fourier spectrometer. H NMR
spectra of DMSO-d6 solutions with TMS as internal standard were recorded on a UNITY 400+ (400 MHz)
instrument. Mass spectra were recorded with Kratos MS-30 instrument with direct insertion of the sample into the
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