TABLE 5. 1H NMR Spectra of Synthesized Compounds
Com-
pound
δ, ppm, SSCC (J, Hz)
15а
2.20 (3Н, s, СН3-4'); 2.46 (6Н, s, СН3C=N and СН3-6); 4.10 (2Н, s, СН2СО);
4.80 (2Н, s, СН2N=); 6.95 (2Н, d, J = 8.5, H-3',5'); 7.11 (2Н, d, J = 8.5, H-2',6');
7.17-7.32 (5Н, m, Нarom); 7.45 (1Н, s, H-7); 7.47 (1Н, d, J = 8.0, Н-5);
7.59 (1Н, d, J = 8.0, H-4); 10.25 (1Н, s, NH)
15b
2.42 (6Н, s, СН3C=N and СН3-6); 3.95 (2Н, s, СН2СО); 4.77 ( 2Н, s, СН2N=);
6.36 (2Н, m, Н*fur-3,4); 7.11 (1Н, d, J = 8.0, Н-5); 7.20 (2Н, d, J = 8.7, H-2',6');
7.29 (2Н, d, J = 8.7, H-3',5'); 7.40 (1Н, s, Н-7); 7.52 (1Н, d, Нfur-5);
7.53 (1Н, d, J = 8.0, Н-4); 10.51 (1Н, s, NH)
15c
16
2.42 (6Н, s, СН3C=N and СН3-6); 4.07 (2Н, s, СН2СО); 4.76 (2Н, s, СН2N=); 7.11 (1Н, d,
J = 8.0, H-5); 7.17-7.43 (10Н, m, Нarom); 7.56 (1Н, d, J = 8.0, H-4); 10.40 (1Н, s, NH)
2.15 (3Н, s, СН3-4'); 2.42 (3Н, s, СН3-5); 2.49 (3Н, s, СН3C=N); 4.13 (2Н, s, СН2СО);
4.79 ( 2Н, s, СН2N=); 6.91 (2Н, d, J = 8.3, H-3',5'); 7.03 (2Н, d, J = 8.3, H-2',6');
7.24-7.31 (5Н, m, Нarom); 7.46 (1Н, d, J = 8.2, H-6); 7.78 (1Н, s, H-4);
7.84 (1Н, d, J = 8.2, H-7); 10.48 (1Н, s, NH)
17a
17b
2.14 (3Н, s, СН3-4'); 2.50 (3Н, s, СН3C=N); 3.93 (2Н, s, СН2СО); 4.84 (2Н, s, СН2N=);
6.87 (2Н, d, J = 8.5, H-3',5'); 6.96 (2Н, d, J = 8.5, H-2',6'); 7.04 (1Н, t, J = 8.0, H-6);
7.18 (1Н, t, J= 8.0, H-5); 7.24 (5Н, m, Нarom); 7.42 (1Н, d, J = 8.1, Н-7);
7.64 (1Н, d, J = 7.7, H-4); 10.50 (1Н, s, NHCO); 11.38 (1Н, s, N(1)H)
2.47 (3Н, s, СН3C=N ); 3.63 (3Н, s, СН3O-4'); 3.85 (2Н, s, СН2СО); 4.81 ( 2Н, s,
СН2N=); 6.40 (2Н, m, Нfur-3,4); 6.70 (2Н, d, J = 9.0, Н-3',5'); 7.02 (1Н, t, J = 8.0, H-6);
7.14 (2Н, d, J = 9.0, Н-2',6'); 7.16 (1Н, t, J = 8.0, H-5); 7.39 (1Н, d, J = 8.0, H-7);
7.55 (1Н, m, Нfur-5); 7.62 (1Н, d, J = 7.8, H-4); 10.50 (1Н, s, NHCO); 11.38 (1Н, s, N(1)H)
18
19
20
2.44 (6Н, s, СН3-1,7); 5.40 (2Н, s, СН2); 6.86 (1Н, s, Н-4); 7.13-7.34 (7Н, m, Нarom);
7.92 (1Н, d, J = 8.0, H-5)
2.43 (3Н, s, СН3-6); 2.48 (3Н, s, СН3-1); 5.50 (2Н, s, СН2); 7.17-7.40 (6Н, m,
H-4 and Нphenyl); 7.46 (1Н, d, J = 8.2, H-7); 7.77 (1Н, d, J = 8.2, H-8); 8.09 (1Н, s, Н-5)
2.51 (3Н, s, СН3-1); 5.49 (2H, s, CH2); 6.89 (1Н, s, H-4); 7.05 (1Н, t, J = 7.8, H-7);
7.11 (2Н, d, J = 8.0, H-2',6'); 7.19-7.33 (4Н, m, H-3',4',5',8); 7.43 (1Н, t, J = 8.0, H-6);
7.97 (1Н, d, J = 7.6, H-5); 10.48 (1Н, s, N(9)H)
21
2.46 (3Н, s, СН3-6); 2.56 (3Н, s, COСН3); 4.05 (2Н, s, СН2CO); 4.28 (2Н, d, J = 5.8,
СН2); 7.15-7.30 (6Н, m, Нarom); 7.49 (1Н, s, H-7); 7.64 (2Н, d, J = 8.2, H-4);
8.53 (1Н, t, J = 5.8, NH)
22
2.46 (3Н, s, СН3-5); 2.60 ( 3Н, s, COСН3); 4.25 (2Н, s, СН2); 4.42 (2Н, d, J = 5.8, СН2);
7.21-7.43 (6Н, m, Нarom); 7.85 (1Н, d, J = 8.0, H-7); 7.92 (1Н, s, H-4);
8.67 (1Н, t, J = 5.8, NH)
23
2.60 ( 3Н, s, COСН3); 4.03 (2Н, s, СН2); 4.26 (2Н, d, J = 5.8, СН2); 7.05 (1Н, t, J = 8.0,
H-6); 7.16-7.31 (6Н, m, Нarom); 7.43 (1Н, d, J = 8.2, H-7); 7.71 (1Н, d, J = 8.2, H-4);
8.38 (1Н, t, J = 5.8, NH); 11.59 (1Н, s, N(1)H)
24a
24b
25
2.14 (3Н, s, СН3-7); 2.22 (3Н, s, СН3-4'); 2.40 ( 3Н, s, СН3C=N); 3.87 (2Н, s, СН2);
6.99 (2Н, s, NН2); 7.07 (2Н, d, J = 7.8, H-3',5',5); 7.34 (1Н, s, H-7);
7.43 (2Н, d, J = 7.8, H-2',6',4); 10.20 (1Н, s, NH)
2.17 (3Н, s, СН3-6); 2.43 (3Н, s, СН3C=N); 3.89 (2Н, s, СН2); 6.97 (2Н, s, NН2);
7.07 (1Н, d, J = 8.0, Н-5); 7.30 (2Н, d, J = 8.6, Н-2',6'); 7.32 (1Н, s, H-7);
7.46 (1Н, d, J = 8.0, H-4); 7.60 (2Н, d, J = 8.6, H-3',5'); 10.44 (1Н, s, NH)
2.21 (6Н, s, СН3C=N and СН3-4'); 3.80 (2Н, s, СН2); 6.77 (2Н, s, NН2);
6.95-7.12 (4Н, m, H-3',5',5,6); 7.33 (1Н, d, J = 7.7, H-7); 7.41 (2Н, d, J = 8.2, H-2',6');
7.54 (1Н, d, J = 7.7, H-4); 10.50 (1Н, s, CONH); 11.09 (1Н, s, N(1)H)
_______
* Hfur: here and elsewhere, the proton of the 2-furyl substituent.
Thus when the 3-arylamino-1-methylhetero[2,3-c]pyrylium salts 1-3 enter into reactions with
nucleophilic reagents in alcohol, addition of the nucleophile at the position 1 of the pyrylium moiety and
opening of the pyrylium ring occur, while in the analogous reaction in acetic acid, subsequent heterocyclization
of the addition products occurs to form derivatives of 2-aryl-1-methylbenzofuro-, 2-aryl-1-methylbenzothieno-,
and 2-aryl-1-methylindolo[2,3-c]pyridin-3(2H)-ones.
522