TABLE 2. 1H NMR Spectra of the Synthesized Compounds 5a-i
Com-
pound
Chemical shifts, , ppm (J, Hz)
1.65 (3Н, br. s, СН3); 1.67-2.12 (4Н, m, 2СН2); 2.12-2.30 (2Н, m, СН2);
2.44-2.69 (2Н, m, СН2); 2.72-2.98 (2Н, m, СН2); 3.04-3.26 (1Н, m, СН);
5.42 (1Н, br. s, =СН); 7.07 (1Н, d, J = 8.1, H Ar); 7.31 (1Н, t, J = 8.1, H Ar);
7.41-7.49 (1Н, m, H Ar); 7.52-7.60 (2Н, m, H Ar); 7.77-7.90 (2Н, m, H Ar);
8.10 (1Н, d, J = 7.3, H Ar); 10.30 (1Н, s, NH); 11.10 (1Н, s, NH)
5a
1.63 (3Н, br. s, СН3); 1.86-2.28 (4Н, m, 2СН2); 2.14-2.28 (2Н, m, СН2);
2.40-2.70 (2Н, m, СН2); 2.98-3.21 (2Н, m, СН2); 3.23-3.35 (1Н, m, СН);
5.40 (1Н, br. s, =СН); 7.28 (1Н, d, J = 7.3, H Ar); 7.45-7.62 (3Н, m, H Ar);
7.69-7.89 (2Н, m, H Ar); 8.11 (2Н, d, J = 7.3, H Ar); 10.45 (1Н, s, NH); 11.05 (1Н, s, NH)
5b
5c
1.64 (3Н, br. s, СН3); 1.88-2.00 (4Н, m, 2СН2); 2.20-2.49 (2Н, m, СН2);
2.49-2.81 (2Н, m, СН2); 2.81-3.00 (2Н, m, СН2); 3.05-3.16 (1Н, m, СН);
3.62 (3Н, s, СН3O); 5.41 (1Н, br. s, =СН); 6.68 (1Н, d, J = 10.8, H Ar);
7.14-7.29 (1Н, m, H Ar); 7.39 (2Н, t, J = 8.1, H Ar); 7.96-8.20 (3Н, m, H Ar);
8.61 (1Н, s, H Ar); 9.95 (1Н, s, NH); 11.04 (1Н, s, NH)
1.67 (3Н, br. s, СН3); 1.89-2.16 (4Н, m, 2СН2); 2.17-2.35 (2Н, m, СН2);
2.53-2.92 (2Н, m, СН2); 2.93-3.10 (2Н, m, СН2); 3.27-3.30 (1Н, m, СН);
5.46 (1Н, br. s, =СН); 6.40 (1Н, d, J = 8.1, H Ar); 6.49-6.63 (1Н, m, H Ar);
7.13-7.53 (2Н, m, H Ar); 7.68 (1Н, d, J = 9.9, H Ar); 7.98 (1Н, d, J = 8.0, H Ar);
8.16 (1Н, t, J = 8.1, H Ar); 8.6 (1Н, s, H Ar); 11.13 (1Н, s, NH); 12.44 (1Н, s, NH)
5d
5e
5f
1.62 (3Н, br. s, СН3); 2.20-2.32 (4Н, m, 2СН2); 2.49-2.52 (2Н, m, СН2);
2.56-2.81 (2Н, m, СН2); 2.84-2.88 (2Н, m, СН2); 3.30-3.36 (1Н, m, СН);
5.42 (1Н, br. s, =СН); 7.51-7.60 (1Н, m, H Ar); 7.58 (1Н, d, J = 8.0, H Ar);
7.83-7.92 (3Н, m, H Ar); 8.10 (1Н, d, J = 8.0, H Ar); 8.32 (2Н, d, J = 8.0, H Ar);
10.74 (1Н, s, NH); 11.03 (1Н, s, NH)
1.65 (3Н, br. s, СН3); 1.66-1.74 (1H, m) and 1.95-2.10 (3Н, m, 2CH2);
2.12-2.27 (2Н, m, СН2); 2.51 (3H, s, COCH3); 2.58-2.67 (1Н, m) and
2.78-2.97 (3Н, m, 2СН2); 3.10-3.19 (1Н, m, СН); 5.40 (1Н, br. s, =СН);
7.51 (1Н, t, J = 7.3, H Ar); 7.54 (1Н, d, J = 8.0, H Ar); 7.72 (2Н, d, J = 8.7, H Ar);
7.81 (1Н, t, J = 7.3, H Ar); 7.90 (2Н, d, J = 8.7, H Ar); 8.10 (1Н, d, J = 8.0, H Ar);
10.43 (1Н, s, NH); 11.03 (1Н, s, NH)
1.59 (3Н, br. s, СН3); 1.88-2.05 (4Н, m, 2СН2); 2.22-2.27 (2Н, m, СН2);
2.35-2.40 (6Н, m, 2СН3); 2.52-2.54 (2Н, m, СН2); 2.66-2.70 (2Н, m, СН2);
3.03-3.10 (1Н, m, СН); 5.36 (1Н, br. s, =СН); 6.60 (1Н, br. s, H Ar); 7.16 (2Н, s, H Ar);
7.47 (1Н, t, J = 7.0, H Ar); 7.53 (1Н, d, J = 7.8, H Ar); 7.80 (1Н, t, J = 7.0, H Ar);
8.15 (1Н, d, J = 7.8, H Ar); 9.86 (1Н, s, NH); 10.97 (1Н, s, NH)
5g
5h
1.61 (3Н, br. s, СН3); 1.87-2.25 (4Н, m, 2СН2); 2.48-2.62 (2Н, m, СН2);
2.68-2.81 (2Н, m, СН2); 2.82-2.95 (2Н, m, СН2); 3.02-3.13 (1Н, m, СН);
3.78 (3Н, br. s, СН3O); 5.36 (1Н, br. s, =СН); 6.81 (1Н, t, J = 7.4, H Ar);
6.94-7.04 (2Н, m, H Ar); 7.48 (1Н, t, J = 7.4, H Ar); 7.59 (1Н, d, J = 7.8, H Ar);
7.80 (1Н, t, J = 7.0, H Ar); 7.87 (1Н, d, J = 7.8, H Ar); 8.05 (1Н, d, J = 7.0, H Ar);
9.18 (1Н, s, NH); 10.97 (1Н, s, NH)
1.59 (3Н, br. s, СН3); 1.90-2.06 (4Н, m, 2СН2); 2.12-2.27 (2Н, m, СН2);
2.48-2.60 (2Н, m, СН2); 2.69-2.87 (2Н, m, СН2); 3.02-3.16 (1Н, m, СН);
5.32 (1Н, br. s, =СН); 7.42 (2Н, d, J = 9.0, H Ar); 7.48 (1Н, t, J = 7.8, H Ar);
7.52 (3Н, m, H Ar); 7.77-7.82 (1Н, m, H Ar); 8.07 (1Н, d, J = 7.8, H Ar);
10.18 (1Н, s, NH); 10.98 (1Н, s, NH)
5i
EXPERIMENTAL
1H NMR spectra were recorded on a Varian Mercury BB instrument (200 MHz) using DMSO-d6 with
TMS as internal standard. The purity of the compounds synthesized was monitored by TLC on Merck Silica Gel
60 F254 plates in a chloroform–ethanol (9:1) solvent system.
3-{3-[(4-Methylcyclohex-3-enylcarbonyl)amino]-4-oxo-3,4-dihydroquinazolin-2-yl}propanoic acid
(4). A. Compound 3b [3] (3.17 g, 0.01 mol) was refluxed in pyridine (25 ml) for 3 h. The product was cooled,
poured into water, filtered, and the residue on the filter was washed with ethanol and dried to give the N,N'-di-
360