KHALTURINA et al.
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spectrum, δ, ppm, form A: 1.32 s (6H, 2Me), 2.99 s (2H,
C4H2), 6.51 s (1H, C5H), 7.15 s (1H, C2H), 7.37–8.01
group of signals (8H, 2C6H4), 12.07 s (1H, NH),
15.84 br.s (1H, OH); form B: 1.27 s (6H, 2Me), 2.95 s
(2H, C4H2 isoquin.), 4.49 s (2H, C2H2), 6.29 s (1H, C5H),
7.35–8.00 group of signals (8H, 2C6H4), 11.56 s (1H,
NH). Found, %: C 61.87; H 4.80; N 3.11. C22H20BrNO3.
Calculated, %: C 61.98; H 4.73; N 3.29.
138–140°C (decomp., ethanol). IR spectrum, cm–1:
3170 br (NH in H-bond, OH in H-bond), 1601 br (CO in
H-bond). H NMR spectrum, δ, ppm, form A: 1.31 s
1
(6H, 2Me), 2.41 s (3H, 4-MeC6H4), 2.90 s (2H, C4H2),
3.86 s (3H, OMe), 3.87 s (3H, OMe), 6.42 s (1H, C5H),
6.97 s (1H, CHarom), 7.11 s (1H, C2H), 7.30 s (1H, CHarom),
7.38–7.96 group of signals (4H, C6H4), 12.07 s (1H, NH),
15.89 br.c (1H, OH); form B: 1.27 s (6H, 2Me), 2.40 s
(3H, 4-MeC6H4), 2.86 s (2H, C4H2 isoquin.), 3.85 s (3H,
OMe), 3.86 s (3H, OMe), 4.49 s (2H, C2H2), 6.21 s (1H,
C5H), 6.96 s (1H, CHarom), 7.26 C (1H, CHarom), 7.35–
7.89 group of signals (4H, C6H4), 11.61 s (1H, NH).
Found, %: C 71.23; H 6.27; N 3.51. C25H27NO5.
Calculated, %: C 71.24; H 6.46; N 3.32.
(2Z,5Z)-5-[3-Butyl-3-methyl-3,4-dihydroiso-
quinolin-1(2H)-ylidene]-3-hydroxy-1-(4-tolyl)-pent-
2-ene-1,4-dione (IIIf). Yield 84%, mp 157–159°C
(decomp., ethanol). IR spectrum, cm–1: 3180 br (NH in
H-bond, OH in H-bond), 1593 br (CO in H-bond). 1H NMR
spectrum, δ, ppm, form A: 1.06 t (3H, CH3CH2CH2CH2,
J 7.0 Hz), 1.22–1.31 group of signals (6H, CH2CH2CH2),
1.27 s (3H, C3Me), 2.41 s (3H, 4-MeC6H4), 2.91 br.s
(2H, C4H2 isoquin.), 6.45 s (1H, C5H), 7.11 s (1H, C2H),
7.34–7.98 group of signals (8H, 2C6H4), 12.17 s (1H,
NH), 16.11 br.s (1H, OH); form B: 0.99 t (3H,
CH3CH2CH2CH2, J 7.0 Hz), 1.16–1.25 group of signals
(6H, CH2CH2CH2), 1.24 s (3H, C3Me), 2.40 s (3H,
4-MeC6H4), 2.88 br.s (2H, C4H2 isoquin.), 4.45 s (2H,
C2H2), 6.24 s (1H, C5H), 7.34–7.93 group of signals (8H,
2C6H4), 11.68 s (1H, NH). Found, %: C 77.24; H 7.36;
N 3.28. C26H29NO3. Calculated, %: C 77.39; H 7.24;
N 3.47.
(2Z,5Z)-3-Hydroxy-5-[3,3-dimethyl-6,7-
dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene]-
1-(4-chlorophenyl)pent-2-ene-1,4-dione (IIIi). Yield
85%, mp 153–155°C (decomp., ethanol). IR spectrum,
cm–1: 3160 br (NH in H-bond, OH in H-bond), 1599 br
(CO in H-bond). 1H NMR spectrum, δ, ppm, form A:
1.31 s (6H, 2Me), 2.90 s (2H, C4H2), 3.86 s (3H, OMe),
3.87 s (3H, OMe), 6.43 s (1H, C5H), 6.98 s (1H, CHarom),
7.13 s (1H, C2H), 7.30 s (1H, CHarom), 7.63–8.08 group
of signals (4H, C6H4), 12.08 s (1H, NH), 15.81 br.s (1H,
OH); form B: 1.27 s (6H, 2Me), 2.87 s (2H, C4H2 isoquin.),
3.85 s (3H, OMe), 3.86 s (3H, OMe), 4.48 s (2H, C2H2),
6.22 s (1H, C5H), 6.96 s (1H, CHarom), 7.26 s (1H,
CHarom), 7.62–8.01 group of signals (4H, C6H4), 11.60 s
(1H, NH). Found, %: C 65.17; H 5.60; N 3.07.
C24H24ClNO5. Calculated, %: C 65.23; H 5.47; N 3.17.
(2Z,5Z)-3-Hydroxy-5-[3,3-dimethyl-6,7-
dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene]-
1-phenylpent-2-ene-1,4-dione (IIIg). Yield 88% (a),
92% (b), mp 174–176°C (decomp., ethyl acetate). IR
spectrum, cm–1: 3170 br (NH in H-bond, OH in H-bond),
(2Z,5Z)-3-Hydroxy-5-[3,3-dimethyl-6,7-di-
methoxy-3,4-dihydroisoquinolin-1(2H)-ylidene]-1-
(4-methoxyphenyl)pent-2-ene-1,4-dione (IIIj). Yield
86% (a), 91% (b), mp 153–155°C (decomp., ethanol).
IR spectrum, cm–1: 3170 br (NH in H-bond, OH in H-
bond), 1597 br (CO in H-bond). 1H NMR spectrum, δ,
ppm, form A: 1.31 s (6H, 2Me), 2.90 s (2H, C4H2), 3.86
s (3H, OMe), 3.87 s (3H, OMe), 3.87 s (3H, 4-
MeOC6H4), 6.42 s (1H, C5H), 6.97 s (1H, CHarom), 7.07
s (1H, C2H), 7.29 s (1H, CHarom), 7.09–8.06 group of
signals (4H, C6H4), 12.08 s (1H, NH), 16.20 br.s (1H,
OH); form B: 1.27 s (6H, 2Me), 2.87 s (2H, C4H2 isoquin.),
3.76 C (3H, OMe), 3.78 s (3H, OMe), 3.83 s (3H,
4-MeOC6H4), 4.34 s (2H, C2H2), 6.21 s (1H, C5H),
6.96 s (1H, CHarom), 7.26 s (1H, CHarom), 7.06–7.96 group
of signals (4H, C6H4), 11.62 s (1H, NH). Found, %:
C 68.64; H 6.31; N 3.16. C25H27NO6. Calculated, %:
C 68.64; H 6.22; N 3.20.
1
1599 br (CO in H-bond). H NMR spectrum, δ, ppm,
form A: 1.32 s (6H, 2Me), 2.90 s (2H, C4H2), 3.86 s (3H,
OMe), 3.87 s (3H, OMe), 6.43 s (1H, C5H), 6.98 s (1H,
CHarom), 7.14 s (1H, C2H), 7.30 s (1H, CHarom), 7.56–
8.06 group of signals (5H, Ph), 12.07 s (1H, NH), 15.96
br.s (1H, OH); form B: 1.27 s (6H, 2Me), 2.87 s (2H,
C4H2 isoquin.), 3.85 s (3H, OMe), 3.86 s (3H, OMe),
4.49 s (2H, C2H2), 6.22 s (1H, C5H), 6.96 s (1H, CHarom),
7.26 s (1H, CHarom), 7.55–8.00 group of signals (5H, Ph),
11.61 s (1H, NH). 13C NMR spectrum, δ, ppm: 27.37
(2Me), 49.96 (Ci4soquin), 55.74 (MeO), 55.84 (MeO), 84.81
(C3isoquin), 93.52 (C5), 112.03 (C2), 118.36–152.58 (CAr),
159.50 (C3), 179.37 (Ci1soquin.), 181.91 (C4), 187.51 (C1).
Found, %: C 70.57; H 6.30; N 3.41. C24H25NO5.
Calculated, %: C 70.75; H 6.18; N 3.44.
(2Z,5Z)-3-Hydroxy-5-[3,3-dimethyl-6,7-di-
methoxy-3,4-dihydroisoquinolin-1(2H)-ylidene]-1-
(4-tolyl)pent-2-ene-1,4-dione (IIIh). Yield 87%, mp
(2Z,5Z)-3-Hydroxy-5-[3,3-dimethyl-6,7-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 5 2009