TABLE 2 (continued)
1
2
3
3b
3c
2225, 1620,
1100
3.10 (3Н, s, СН3); 3.27 (3Н, s, СН3); 4.20 (3Н, s, ОСН3);
4.30 (3Н, s, ОСН3); 6.03 (2Н, s, СН2); 7.10-7.55 (5Н, m, Н arom.);
7.67 (1Н, s, Н arom.); 7.83 (1Н, s, Н arom.)
2225, 1625,
1100
2.57 (3Н, s, СН3); 2.72 (3Н, s, СН3); 3.85 (3Н, s, ОСН3);
3.90 (3Н, s, ОСН3); 4.06 (2Н, s, СН2 Fur); 6.07 (1Н, s,
Н arom. Fur); 6.55 (1Н, s, Н arom. Fur); 6.68 (1Н, s, Н arom. Fur);
7.09 (1Н, s, Н arom.); 8.01 (1Н, s, Н arom.)
3d
3e
3370, 3300,
2230, 1635,
1100
3250, 2220,
1630, 1100
2.90 (3Н, s, СН3); 3.13 (3Н, s, СН3); 3.96 (3Н, s, ОСН3);
4.03 (3Н, s, ОСН3); 7.23 (1Н, s, Н arom.); 7.67 (1Н, s, Н arom.)
2.56 (3Н, s, СН3); 3.14 (3Н, s, СН3); 4.07 (3Н, s, ОСН3);
4.09 (3Н, s, ОСН3); 6.58 (2Н, d, Н arom.); 6.99 (1Н, t, Н arom.);
7.12 (1Н, s, Н arom.); 7.32 (2Н, t, Н arom.); 7.82 (1Н, s, Н arom.);
11.72 (1Н, br. s, N–H)
4
3320, 2230,
1605, 1100
2.83 (3Н, s, СН3); 2.95 (3Н, s, СН3); 3.97 (6Н, s, 2ОСН3);
4.55 (2Н, s, СН2); 5.63 (2Н, s, СН2); 6.60 (1Н, s, Н arom.);
6.77-7.27 (11Н, m, Н arom.)
5a
5b
3250, 2200,
1640
1.57 (3Н, s, СН3); 1.88 (3Н, s, СН3); 3.73 (3Н, s, ОСН3);
3.76 (3Н, s, ОСН3); 6.02 (1Н, br. s, N–Н); 6.69 (1Н, s, Н arom.);
6.91 (1Н, s, Н arom.)
2200, 1640
1.93 (3Н, s, СН3); 3.78 (3Н, s, ОСН3); 3.82 (3Н, s, ОСН3);
6.84 (1Н, s, Н arom.); 7.05-7.20 (1Н, t, J = 7.5, Н arom.);
7.43 (2Н, t, J = 7.5, Н arom.); 7.73 (2Н, d, J = 7.5, Н arom.);
8.92 (1Н, s, Н arom.)
6
3400, 2200
3.54 (3Н, s, ОСН3); 3.61 (3Н, s, ОСН3); 4.00 (2Н, d, СН2,
J = 6.2); 6.52-6.67 (3Н, m, Н arom.); 7.04-7.32 (10Н, m,
Н arom.); 10.50 (1Н, t, J = 6.2, N–H)
7
8
3200, 2225,
1640, 1610, 1100
3.17 (3Н, s, СН3); 4.10 (3Н, s, ОСН3); 7.43-7.87 (7Н, m, Н arom.)
1620
3.23 (3Н, s, СН3); 3.80 (3Н, s, ОСН3); 4.07 (3Н, s, ОСН3);
7.67 (7Н, s, Н arom.)
_______
1
* The H NMR spectra were taken in CF3COOH (for compounds 2a-d,
3a,b,d, 4, 7, and 8) and in DMSO-d6 (for compounds 3c,e, 5a,b, and 6).
EXPERIMENTAL
1
The IR spectra were recorded in nujol on a UR 20 spectrophotometer, and the H NMR spectra were
taken on a Varian Gemini 200 (200 MHz) spectrometer, internal standard was TMS.
The physicochemical and spectral characteristics of the compounds synthesized are given in Tables 1
and 2.
4-Cyano-6,7-dimethoxyisoquinolines 2a-d. Perchlorate 1 (5 mmol) was added in one portion to
mixture of aqueous 25% ammonia solution (5 ml) and 2-propanol (8 ml). The reaction mixture was stirred for
1-2 h, isoquinoline 2 was filtered off, washed with water, and crystallized from alcohol.
1,3-Dialkyl-4-cyano-6,7-dimethoxy-2-R-isoquinolinium Perchlorates 3a-e. Perchlorate 1 (5 mmol)
was added to solution of primary amine or hydrazine (5.5 mmol) in 2-propanol (10 ml) and the mixture stirred at
20-40°C until complete dissolution. After 4-6 h solid isoquinoline perchlorate 3 was filtered off, washed with
alcohol, and with ether, and dried.
2-Benzyl-6-benzylamino-4-cyano-7-methoxy-1,3-dimethylisoquinolinium Perchlorate (4). A.
Mixture of perchlorate 1 (5 mmol) and benzylamine (25 mmol) was boiled in ethanol for 6 h, then left overnight.
The precipitated solid was filtered off, and crystallized from ethanol.
1425