1
Compound 4b. The yield 84%; mp 223-225°C. IR spectrum, ν, cm−1: 3434 (NH), 2224 (C≡N). H
3
NMR spectrum, δ, ppm (J, Hz): 3.88 (3Н, s, 4-СН3O); 7.17 (2Н, d, J = 8.5, Н-3,5 Аг); 7.25 (2Н, m, Н-5,6);
7.61 (2Н, m, Н-4,7); 8.01 (2Н, d, 3J = 8.5, Н-2,6 Аr); 8.28 (1H, s, =CH─Ph); 13.00 (1H, br. s, NH). Found, %:
N 15.30. C17H13N3O. Calculated, %: N 15.26.
2-(4-Oxo-3,4-dihydro-2-quinazolinyl)- and 2-(1H-Benzo[d]imidazol-2-yl)acetonitriles 5a and 5b.
To compound 1a,b (1.2 mmol) in 2-propanol (10 ml) we added 3-4 drops of pyrrolidine (or 2-3 drops of
hydrochloric acid). The mixture was heated for 1-2 h until the initial compound 1 had disappeared according to
TLC. The pH of the reaction mixture was then brought to 7. The precipitate was filtered off, washed with water,
and dried. A small quantity of the product 5a,b can be isolated from the mother solution by adding 5-10 ml of
water. The yield of compound 5a was 92%, and the yield of compound 5b was 87%.
(2E)-6-Hydroxy-2-(4-methylene-3,4-dihydro-2(1H)-quinazylidene)-3-oxohexanenitrile (6). To a
suspension of compound 1a (0.51 g, 2 mmol) in ethanol (or 2-propanol) (20 ml) we added 1.04 ml of a 10%
aqueous solution of NaOH. The mixture was boiled for 2-3 h while the end of the reaction was monitored by
chromatography. The reaction mixture was cooled, and the pH of the mixture was brought to 7. The precipitate
was filtered off, washed with water and with alcohol, and dried. A small quantity of the product 6 can be
isolated from the mother solution by adding 10 ml of water. The yield 88%; mp 221°C. IR spectrum, ν, cm−1:
2900-3400 (NH, ОН), 2210 (C≡N), 1690 (NHС=О), 1645 (С=О), 1600 (C=CCN). 1H NMR spectrum, δ, ppm (J,
3
3
Hz): 1.75 (2Н, m, CH2CH2CH2); 2.68 (2Н, t, J = 7.6, СОСН2); 3.44 (2Н, t, J = 6.3, СН2ОН); 4.31 (1Н, br. s,
ОН); 7.38 (1Н, t, 3J = 7.8, Н-6); 7.74 (1Н, t, 3J = 7.8, Н-7); 7.8 (1Н, br. s, Н-8); 8.0 (1Н, d, 3J = 7.8, Н-5); 11.56
(1Н, br. s, 1-NH); 13.97 (1H, br. s, 3-NH). Found, %: N 15.35. С14Н13N3O3. Calculated, %: N 15.49.
2-(4-Oxo-3,4-dihydro-2-quinazolinyl)acetonitrile (5a). To compound 6 (0.43 g, 1.6 mmol) in
2-propanol (15 ml) we added 30% aqueous solution of NaOH (0.2 ml) (or 2-3 drops of hydrochloric acid). The
mixture was heated for 1-2 h until the initial compound 6 had disappeared according to TLC. The pH of the
reaction mixture was then brought to 7. The precipitate was filtered off, washed with water and with alcohol,
and dried. A small quantity of the product 6 can be isolated from the mother solution by adding 10 ml of water,
The yield was 83%.
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