Chemistry of Heterocyclic Compounds 2017, 53(10), 1114–1119
temperature at or below 25°С. The benzene layer was
8.97 (1Н, s, NH); 9.30 (1Н, s, NH of ring). 13C NMR
spectrum, δ, ppm: 28.4 (2C); 41.40; 48.6; 78.6; 118.4; 121.8;
124.1; 126.9; 128.6; 128.7 (2C); 129.2 (2C); 130.3; 135.2;
139.9; 152.0; 156.2; 170.8. Mass spectrum, m/z (Irel, %):
350 [M]+ (9), 200 (100), 15 (3), 158 (19), 143 (7), 120 (6),
119 (18), 91 (6). Found, %: С 68.43; Н 6.21; N 16.07.
C20H22N4О2. Calculated, %: С 68.55; Н 6.33; N 15.99.
(Z)-2-[2-(2'H-Spiro[cyclopentane-1,3'-isoquinolin]-1'(4'H)-
ylidene)acetyl]-N-phenylhydrazine-1-carboxamide (9b)
was obtained analogously to the procedure for preparation
of compound 7 from nitrile 4 (4.36 g, 20 mmol) and
carbinol 6b (3.52 g, 20 mmol). Yield 4.29 g (57%), colorless
crystals, mp 127–128°С (2-propanol). IR spectrum, ν, cm–1:
1610 (С=О of chelate), 1670 (С=О), 3100–3370 (NH of
separated, the aqueous phase was neutralized with aqueous
25% ammonia solution while cooling with ice and
maintaining the mixture at 20°С. The precipitate that
formed was filtered off, dried, and recrystallized. Yield
2.68 g (42%), colorless crystals, mp 169–170°С (2-propa-
nol). IR spectrum, ν, cm–1: 1640 (С=N), 1610 (С=О of
chelate), 3150–3300 (NH of chelate and NH of hydrazone).
1H NMR spectrum, δ, ppm: 1.22 (6H, s, 2CH3); 2.86 (2H,
s, 4-СН2); 8.02 (1Н, s, HC=N); 7.28–7.78 (9Н, m, H Ph);
9.83 (1H, s, NH); 10.67 (1Н, s, NH of ring). 13C NMR
spectrum, δ, ppm: 28.4 (2C); 41.3; 48.7; 76.6; 124.6; 126.5
(2C); 127.0; 127.8; 128.6; 128.8 (2C); 129.1; 129.2; 130.6;
135.0 (2С); 140.1; 153.1. Mass spectrum, m/z (Irel, %): 319
[M]+ (14), 200 (100), 159 (5), 158 (15), 119 (9). Found, %:
С 75.08; Н 6.52; N 13.23. C20H21N3О. Calculated, %:
С 75.21; Н 6.63; N 13.16.
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chelate and free NH). H NMR spectrum, δ, ppm: 1.50–
1.67 (8H, m, 4CH2); 2.90 (2H, s, 4-СН2); 5.25 (1Н, s,
НС=); 6.92–7.59 (9Н, m, H Ph); 7.78 (1Н, s, NHPh); 8.68
(1H, s, NH); 9.02 (1Н, s, NH); 9.51 (1Н, s, NH of ring).
13C NMR spectrum, δ, ppm: 23.0 (4C); 40.9; 48.6; 78.6;
118.4; 122.0; 124.1; 126.9; 128.7; 128.8 (2C); 129.3(2C);
130.5; 135.3; 140.0; 152.0; 156.2; 170.4. Mass spectrum,
m/z (Irel, %): 376 [M]+ (9), 226 (100), 184 (5), 120 (8), 119
(37), 92 (8). Found, %: С 70.07; Н 6.35; N 15.02.
C22H24N4О2. Calculated, %: С 70.19; Н 6.43; N 14.88.
(Z)-5-[(3,3-Dimethyl-3,4-dihydroisoquinolin-1(2H)-yl-
idene)methyl]-N-phenyl-1,3,4-thiadiazol-2-amine (10а) was
obtained analogously to the procedure for preparation of
compound 7 from nitrile 5 (4.68 g, 20 mmol) and carbinol
6a (3.0 g, 20 mmol) by stirring for 0.5 h. Yield 2.23 g
(64%), yellow crystals, mp 190°С (decomp.). IR spectrum,
ν, cm–1: 1640 (С=С), 3100–3270 (NH of chelate and
(Z)-N'-[2-(3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-
ylidene)acetyl]benzohydrazide (8а) was obtained
analogously to the procedure for preparation of compound
7 from nitrile 3 (4.06 g, 20 mmol) and carbinol 6а (3.0 g,
20 mmol). Yield 4.08 g (61%), colorless crystals, mp 169–
170°С (2-propanol). IR spectrum, ν, cm–1: 1610 (С=О of
chelate), 1670 (С=О), 3100–3380 (NH of chelate and free
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NH). H NMR spectrum, δ, ppm: 1.18 (6H, s, 2CH3); 2.82
(2H, s, 4-СН2); 5.29 (1Н, s, НС=); 7.26–7.90 (9Н, m,
H Ph); 9.21 (1H, s, NH); 9.33 (1Н, s, 1NH); 10.10 (1Н, s,
NH of ring). 13C NMR spectrum, δ, ppm: 28.4 (2C); 41.3;
49.0; 78.5; 118.4; 121.8; 124.1; 126.9; 128.6; 128.7 (2C);
129.4 (2C); 130.4; 135.4; 140.0; 152.1; 156.4; 171.0. Mass
spectrum, m/z (Irel, %): 335 [M]+ (12), 200 (100), 159 (7),
158 (12), 105 (80), 77 (63). Found, %: С 71.57; Н 6.18;
N 12.61. C20H21N3О2. Calculated, %: С 71.62; Н 6.31; N 12.53.
(Z)-N'-[2-(2'H-Spiro[cyclopentane-1,3'-isoquinolin]-
1'(4'H)-ylidene)acetyl]benzohydrazide (8b) was obtained
analogously to the procedure for preparation of compound
7 from nitrile 3 (4.06 g, 20 mmol) and carbinol 6b (3.52 g,
20 mmol). Yield 4.77 g (66%), colorless crystals, mp 213–
214°С (2-propanol). IR spectrum, ν, cm–1: 1610 (С=О of
chelate), 1670 (С=О), 3100–3380 (NH of chelate and free
NH). 1H NMR spectrum, δ, ppm: 1.52–1.69 (8H, m,
4CH2); 2.91 (2H, s, 4-СН2); 5.31 (1Н, s, НС=); 7.28–7.90
(9Н, m, H Ph); 9.24 (1H, s, NH); 9.52 (1Н, s, NH); 10.13
(1Н, s, NH of ring). 13C NMR spectrum, δ, ppm: 23.0 (4C);
38.5; 59.6; 78.9; 124.1; 126,9; 127.5 (3C); 128.4 (2C);
129.1 (2С); 130.2; 131.7; 132.9; 135.8; 166.0; 170.2. Mass
spectrum, m/z (Irel, %): 361 [M]+ (9), 226 (100), 105 (39),
77 (32). Found, %: С 73.04; Н 6.28; N 11.74. C22H23N3О2.
Calculated, %: С 73.11; Н 6.41; N 11.63.
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NHPh). H NMR spectrum, δ, ppm: 1.26 (6H, s, 2CH3);
2.86 (2H, s, 4-СН2); 5.97 (1Н, s, НС=); 6.96–7.81 (9Н, m,
H Ph); 8.78 (1Н, s, NHPh); 10.07 (1Н, s, NH of ring).
13C NMR spectrum, δ, ppm: 28.3 (2C); 41.7; 49.1; 77.4;
119.0; 123.2; 124.2 (2С); 124.3; 125.7 (2С); 126.1; 128.5
(2С); 130.7; 132.0; 136.5; 152.3; 157.5. Mass spectrum,
m/z (Irel, %): 348 [M]+ (100), 347 (41), 333 (56), 91 (8), 77
(27). Found, %: С 68.85; Н 5.61; N 16.15; S 9.03.
C20H20N4S. Calculated, %: С 68.94; Н 5.79; N 16.08; S 9.20.
(Z)-5-((2'H-Spiro[cyclopentane-1,3'-isoquinolin]-1'(4'H)-
ylidene)methyl)-N-phenyl-1,3,4-thiadiazol-2-amine (10b)
was obtained analogously to the procedure for preparation
of compound 10a from nitrile 5 (4.68 g, 20 mmol) and
carbinol 6b (3.52 g, 20 mmol). Yield 2.28 g (61%), yellow
crystals, mp 218°С (decomp.). IR spectrum, ν, cm–1: 1640
1
(С=С), 3100–3270 (NH of chelate and NHPh). H NMR
spectrum, δ, ppm: 1.58–1.78 (8H, m, 4CH2); 2.94 (2H, s,
4-СН2); 5.98 (1Н, s, НС=); 6.97–7.80 (9Н, m, H Ph); 8.95
(1Н, s, NHPh); 10.08 (1Н, s, NH of ring). 13C NMR spectrum,
δ, ppm: 23.1 (4C); 41.8; 49.1; 77.5; 119.0; 123.2; 124.2
(2С); 124.4; 125.8 (2С); 126.2; 128.5 (2С); 131.1; 132.1;
137.2; 152.4; 158.0. Mass spectrum, m/z (Irel, %): 374 [M]+
(92), 373 (37), 84 (100), 77 (13). Found, %: С 70.47;
Н 5.86; N 15.11; S 8.47. C22H22N4S. Calculated, %:
С 70.56; Н 5.92; N 14.96; S 8.56.
(Z)-2-[2-(3,3-Dimethyl-3,4-dihydroisoquinolin-1(2H)-
ylidene)acetyl]-N-phenylhydrazine-1-carboxamide (9а)
was obtained analogously to the procedure for preparation
of compound 7 from nitrile 4 (4.36 g, 20 mmol) and
carbinol 6а (3.0 g, 20 mmol). Yield 4.35 g (62%), colorless
crystals, mp 183–184°С (2-propanol). IR spectrum, ν, cm–1:
1610 (С=О of chelate), 1670 (С=О), 3120–3380 (NH of
chelate and free NH). 1H NMR spectrum, δ, ppm: 1.18 (6H,
s, 2CH3); 2.81 (2H, s, 4-СН2); 5.24 (1Н, s, НС=); 6.92–
7.61 (9Н, m, H Ph); 7.75 (1Н, s, NHPh); 8.69 (1H, s, NH);
X-ray structural analysis of compound 10b was
performed on an Agilent XCalibur automatic diffractometer
with Agilent EOS two-dimensional CCD detector. The
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