AVETISYAN, GALSTYAN
938
4-Me), 3.75 s (3H, CH3O), 4.54 s (2H, CH2O), 7.33 s
(1H, CH=), 7.70–6.75 m (4H, Harom), 9.15 s (1H, NH).
Found, %: C 62.44; H 5.85; N 3.27. C21H23NO7. Cal-
culated, %: C 62.83; H 5.77; N 3.48.
(C=O, lactone), 1717 (C=O, ester), 1650 (C=O, imide),
1620 (C=O, ketone), 1612 (C=C). H NMR spectrum,
1
δ, ppm: 1.12 d (3H, CH3), 1.84–1.26 m (10H, (CH2),
2.44 s (3H, 4-Me), 4.58 s (2H, CH2O), 5.00 q (1H,
CH), 8.00–7.80 m (4H, Harom). Found, %: C 65.10;
H 5.22; N 3.38. C23H23NO7. Calculated, %: C 64.93;
H 5.45; N 3.29.
2-(4-Methyl-2-oxo-5,5-pentamethylene-2,5-dihy-
drofuran-3-yl)-2-oxoethyl 2-acetamido-3-(4-me-
thoxyphenyl)prop-2-enoate (IIIh). Yield 72%,
mp 123–125°C, Rf 0.56. IR spectrum, ν, cm–1: 3300
(NH), 1690 (C=O, amide), 1753 (C=O, lactone), 1710
(C=O, ester), 1630 (C=O, ketone), 1615 (C=C), 1610
2-Oxo-2-(4,5,5-trimethyl-2-oxo-2,5-dihydrofu-
ran-3-yl)ethyl 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-
2-yl)propionate (IIIm). Yield 71%, mp 57–58°C,
Rf 0.83. IR spectrum, ν, cm–1: 1755 (C=O, lactone),
1735 (C=O, ester), 1650 (C=O, imide), 1630 (C=O,
ketone), 1610 (C=C). 1H NMR spectrum, δ, ppm: 1.57 s
(6H, 5-Me), 2.38 s (3H, 4-Me), 3.55 t (2H, CH2), 3.85 t
(2H, CH2), 4.40 s (2H, CH2O), 8.15–7.75 m (4H,
1
(CH=C), 1510 (C=Carom). H NMR spectrum, δ, ppm:
1.24–1.84 m (10H, (CH2), 2.06 s (3H, CH3CO), 2.38 s
(3H, 4-Me), 3.82 s (3H, CH3O), 4.60 s (2H, CH2O),
7.20 d (1H, CH=), 7.64–6.84 m (4H, Harom), 9.32 s
(1H, NH). Found, %: C 65.45; H 5.99; N 3.35.
C24H27NO7. Calculated, %: C 65.29; H 6.16; N 3.17.
H
arom). Found, %: C 62.15; H 5.14; N 3.48.
C20H19NO7. Calculated, %: C 62.33; H 4.97; N 3.63.
2-Oxo-2-(4,5,5-trimethyl-2-oxo-2,5-dihydrofu-
ran-3-yl)ethyl 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-
2-yl)acetate (IIIi). Yield 71%, mp 135–136°C,
Rf 0.81. IR spectrum, ν, cm–1: 1740 (C=O, lactone),
1710 (C=O, ester), 1650 (C=O, imide), 1640 (C=O,
2-(4-Methyl-2-oxo-5,5-pentamethylene-2,5-dihy-
drofuran-3-yl)-2-oxoethyl 3-(1,3-dioxo-2,3-dihydro-
1H-isoindol-2-yl)propionate (IIIn). Yield 70%,
mp 151–153°C, Rf 0.68. IR spectrum, ν, cm–1: 1753
(C=O, lactone), 1717 (C=O, ester), 1645 (C=O, imide),
1
ketone), 1610 (C=C). H NMR spectrum, δ, ppm:
1
1.62 s (6H, 5-Me), 2.24 s (3H, 4-Me), 4.44 s (2H,
CH2O), 5.17 s (2H, CH2N), 7.90–7.75 m (4H, Harom).
Found, %: C 61.14; H 4.88; N 3.45. C19H17NO7. Cal-
culated, %: C 61.45; H 4.61; N 3.77.
1618 (C=O, ketone), 1610 (C=C). H NMR spectrum,
δ, ppm: 1.86–1.24 m (10H, CH2), 2.42 s (3H, 4-Me),
3.60 t (2H, CH2), 3.92 t (2H, CH2), 4.46 q (2H, CH2O),
8.00–7.70 m (4H, Harom). Found, %: C 65.14; H 5.38;
N 3.38. C23H23NO7. Calculated, %: C 64.93; H 5.45;
N 3.29.
2-(4-Methyl-2-oxo-5,5-pentamethylene-2,5-dihy-
drofuran-3-yl)-2-oxoethyl 2-(1,3-dioxo-2,3-dihydro-
1H-isoindol-2-yl)acetate (IIIj). Yield 82%, mp 157–
159°C, Rf 0.70. IR spectrum, ν, cm–1: 1749 (C=O,
lactone), 1722 (C=O, ester), 1655 (C=O, imide), 1621
2-Oxo-2-(4,5,5-trimethyl-2-oxo-2,5-dihydrofu-
ran-3-yl)ethyl 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-
2-yl)-3-methylbutanoate (IIIo). Yield 79%, mp 79–
80°C, Rf 0.81. IR spectrum, ν, cm–1: 1745 (C=O,
lactone), 1720 (C=O, ester), 1645 (C=O, imide), 1630
1
(C=O, ketone), 1608 (C=C). H NMR spectrum, δ,
ppm: 1.86–1.24 m (10H, CH2), 2.38 s (3H, 4-Me),
4.50 s (2H, CH2O), 5.22 s (2H, CH2N), 7.96–7.80 m
(4H, Harom). Found, %: C 64.38; H 5.07; N 3.52.
C22H21NO7. Calculated, %: C 64.23; H 5.15; N 3.40.
1
(C=O, ketone), 1605 (C=C). H NMR spectrum, δ,
ppm: 0.86 d (6H, Me2CH), 1.68 s (6H, 5-Me), 1.80 m
(1H, Me2CH), 2.35 s (3H, 4-Me), 4.44 s (2H, CH2O),
4.58 d (1H, CHN), 8.20–7.70 q (4H, Harom). Found, %:
C 63.66; H 5.88; N 3.21. C22H23NO7. Calculated, %:
C 63.91; H 5.61; N 3.39.
2-Oxo-2-(4,5,5-trimethyl-2-oxo-2,5-dihydrofu-
ran-3-yl)ethyl 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-
2-yl)propionate (IIIk). Yield 85%, mp 88–89°C,
Rf 0.80. IR spectrum, ν, cm–1: 1750 (C=O, lactone),
1715 (C=O, ester), 1655 (C=O, imide), 1650 (C=O,
ketone), 1615 (C=C). 1H NMR spectrum, δ, ppm: 1.18 d
(3H, CH3), 1.58 s (6H, 5-Me), 2.35 s (3H, 4-Me),
4.50 s (2H, CH2O), 4.95 q (1H, CH), 8.10–7.78 m
(4H, Harom). Found, %: C 62.09; H 5.05; N 3.33.
C20H19NO7. Calculated, %: C 62.33; H 4.97; N 3.63.
2-(4-Methyl-2-oxo-5,5-pentamethylene-2,5-dihy-
drofuran-3-yl)-2-oxoethyl 2-(1,3-dioxo-2,3-dihydro-
1H-isoindol-2-yl)-3-methylbutanoate (IIIp). Yield
76%, mp 164–165°C, Rf 0.65. IR spectrum, ν, cm–1:
1749 (C=O, lactone), 1720 (C=O, ester), 1660 (C=O,
1
imide), 1614 (C=O, ketone), 1605 (C=C). H NMR
spectrum, δ, ppm: 0.80 d (6H, Me2CH), 1.84–1.26 m
(10H, CH2), 1.90 m (1H, Me2CH), 2.40 s (3H, 4-Me),
4.58 s (2H, CH2O), 4.60 d (1H, CHN), 8.00–7.70 q
(4Harom). Found, %: C 66.43; H 5.78; N 3.25.
C25H27NO7. Calculated, %: C 66.21; H 6.00; N 3.09.
2-(4-Methyl-2-oxo-5,5-pentamethylene-2,5-dihy-
drofuran-3-yl)-2-oxoethyl 2-(1,3-dioxo-2,3-dihydro-
1H-isoindol-2-yl)propionate (IIIl). Yield 73%,
mp 141–143°C, Rf 0.72. IR spectrum, ν, cm–1: 1753
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 6 2013