TABLE 2. 1H NMR Spectra of Compounds 2a-b, 3a-c, 4a-c
Com-
pound
Chemical shifts, δ, ppm (J, Hz)
2a
2b
2.34 (3Н, s, 6-СН3); 2.46 (3Н, s, 2-СН3); 2.77, 2.88, 3.09, and 3.26 (4Н, four m, CH2CH2);
4.38 (1H, s, 1-CH); 7.08 (1Н, d, J = 8.0, Н-7); 7.29-7.35 (5Н, m, Н Ph); 7.43 (1H, s, Н-5);
7.54 (1Н, d, J = 8.0, Н-8)
2.32 (3Н, s, 6-СН3); 2.47 (3Н, s, 2-СН3); 2.76, 2.87, 3.06, and 3.25 (4Н, four m, CH2CH2);
3.81 (3Н, s, 4'-ОСН3); 4.33 (1H, s, 1-CH); 6.87 (2H, d, J = 8.0, Н-3',5');
7.08 (1Н, d, J = 8.0, Н-7); 7.27 (2H, d, J = 8.0, Н-2',6'); 7.42 (1H, s, Н-5);
7.55 (1Н, d, J = 8.0, Н-8)
2c
2d
2e
2.29 (3Н, s, 6-СН3); 2.44 (3Н, s, 2-СН3); 2.74, 2.86, 3.04, and 3.22 (4Н, four m, CH2CH2);
4.34 (1H, s, 1-CH); 7.08 (1Н, d, J = 8.0, Н-7); 7.29 (4Н, br. s, Н-2',3',5',6');
7.41 (1H, s, Н-5); 7.53 (1Н, d, J = 8.0, Н-8)
2.36 (3Н, s, 6-СН3); 2.49 (3Н, s, 2-СН3); 2.79, 2.90, 3.08, and 3.27 (4Н, four m, СН2СН2);
4.42 (1Н, s, 1-СН); 7.02 (1Н, t, J = 8.0, Н-5'); 7.12 (2Н, m, Н-7,4');
7.19 (1Н, d, J = 8.0, Н-6'); 7.33 (1Н, m, Н-2'); 7.45 (1H, s, Н-5); 7.57 (1Н, d, J = 8.0, Н-8)
2.35 (3Н, s, 6-СН3); 2.48 (3Н, s, 2-СН3); 2.81, 2.91, 3.10, and 3.26 (4Н, four m, СН2СН2);
4.46 (1Н, s, 1-СН); 7.12 (1Н, d, J = 8.0, Н-7); 7.27 (1Н, t, J = 4.8, Н-5');
7.45 (1H, s, Н-5); 7.57 (1Н, d, J = 8.0, Н-8); 7.68 (1Н, d, J = 4.8, Н-4');
8.58 (1H, d, J = 4.8, Н-6'); 8.62 (1H, s, Н-2')
2f
2.46 (3Н, s, 6-СН3); 2.47 (3Н, s, 2-СН3); 2.82, 2.89, 3.02, and 3.30 (4Н, four m, СН2СН2);
4.86 (1Н, s, 1-СН); 6.98 (1Н, t, J = 4.0, Н-4'); 7.12 (2Н, m, Н-5',7);
7.30 (1Н, d, J = 4.0, Н-3'); 7.43 (1H, s, H-5); 7.59 (1Н, d, J = 8.0, H-8)
2g
2h
2.47 (3Н, s, 6-СН3); 2.48 (3Н, s, 2-СН3); 2.83, 2.90, 2.97, and 3.26 (4Н, four m, СН2СН2);
4.81 (1Н, s, 1-СН); 7.03 (1Н, s, Н-5'); 7.14 (1Н, d, J = 8.0, Н-7); 7.20 (1Н, s, Н-4');
7.43 (1H, s, Н-5); 7.61 (1Н, d, J = 8.0, Н-8)
2.49 (3Н, s, 6-СН3); 2.55 (3Н, s, 2-СН3); 2.90, 2.98, 3.02, and 3.32 (4Н, four m, СН2СН2);
4.94 (1Н, s, 1-СН); 6.70 (1Н, s, Н-3'); 7.14 (1Н, d, J = 8.0, Н-7);
7.22-7.27 (2Н, m, Н-5',6'); 7.46 (2H, m, Н-5,4');
7.54 (1Н, d, J = 8.0, Н-8); 7.61 (1Н, d, J = 8.0, Н-7')
3a
3b
3c
3.17, 3.36, 3.47, 3.61 (4H, four m, CH2CH2); 5.90 (1Н, s, 1-СН);
7.36 (1Н, t, J = 8.0, Н-7); 7.43 (1Н, t, J = 8.0, Н-6); 7.45 (3Н, m, Н-3',4',5');
7.61 (2H, m, Н-2',6'); 7.76 (1Н, d, J = 8.0, Н-8); 7.79 (1Н, d, J = 8.0, Н-5);
10.65 (1H, br. s, NH)
3.15, 3.36, 3.44 and 3.59 (4Н, four m, CH2CH2); 3.84 (3H, s, OCH3);
5.83 (1H, s, 1-CH); 6.95 (2H, d, J = 8.0, H-3',5'); 7.35 (1H, t, J = 8.0, H-7);
7.42 (1H, t, J = 8.0, H-6); 7.51 (2H, d, J = 8.0, H-2',6'); 7.74 (1H, d, J = 8.0, H-8);
7.78 (1H, d, J = 8.0, H-5); 10.16 (1H, br. s, NH)
3.19, 3.40, 3.52 and 3.65 (4Н, four m, CH2CH2); 6.19 (1Н, s, 1-СН);
7.38 (1H, t, J = 8.0, H-7); 7.45 (1H, t, J = 8.0, H-6); 7.78 (1H, d, J = 8.0, H-8);
7.81 (1H, d, J = 8.0, H-5); 7.95 (2H, d, J = 8.0, H-2',6'); 8.30 (2H, d, J = 8.0, H-3',5');
10.63 (1H, br. s, NH)
4a
4b
4c
2.77 (3Н, s, 2-СН3); 3.18-3.86 (4Н, m, CH2CH2); 5.92 (1H, s, 1-CH);
7.36 (1H, t, J = 8.0, H-7); 7.44 (1H, t, J = 8.0, H-6); 7.50 (3Н, m, H-3',4',5');
7.73 (2Н, m, H-2',6'); 7.76 (1H, d, J = 8.0, H-8); 7.79 (1H, d, J = 8.0, H-5)
2.77 (3H, s, 2-CH3); 3.14-3.70 (4H, m, CH2CH2); 3.85 (3H, s, OCH3);
5.82 (1Н, br. s, 1-СН); 6.98 (2H, d, J = 8.0, H-3',5'); 7.35 (1H, t, J = 8.0, H-7);
7.42 (1H, t, J = 8.0, H-6); 7.65 (2H, d, J = 8.0, H-2',6'); 7.75 (2Н, d, J = 8.0, H-5,8)
2.78 (3H, s, 2-CH3); 3.20, 3.52, 3.67, and 3.87 (4Н, four m, CH2CH2);
6.20 (1Н, s, 1-СН); 7.37 (1H, t, J = 8.0, H-7); 7.44 (1H, t, J = 8.0, H-6);
7.78 (2H, d, J = 8.0, H-5,8); 8.07 (2H, d, J = 8.0, H-2',6'); 8.30 (2H, d, J = 8.0, H-3',5')
At a temperature of 130-140°C, the reaction was completed in 2 h. In some cases, for example to obtain
compounds 2a-c, increasing the temperature to 160°C shortened the reaction time to 30 min. After cooling, the
crystalline mass was well washed with dry acetone and ether. As a rule, the 2-methyl-1,2,3,4-tetrahydro-
benzothieno[2,3-c]pyridine hydrochlorides did not require additional purification and were spectroscopically
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