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HETEROCYCLES, Vol. 89, No. 3, 2014
13
CH
3
), 6.21 d (1H, CH, J = 5.1 Hz), 7.25 d (1H, CH, J = 5.1 Hz), 7.74–7.83 m (4H, C
6
H ). C NMR
4
spectrum (CDCl
(CHarom), 164.49 (C=O), 164.74 (C=O), 210.03 (=C=); MS: m/z 244 [MH]+, 243 [M]-. Anal. Calcd for
NO (243.21): C 64.20; H 3.73; N 5.76; O 26.31. Found: C 64.21; H 3.74; N 5.73.
3
), δ ppm: 52.62 (CH ), 91.77 (CH), 96.71 (CH), 123.77 (CHarom), 131.76 (Carom), 134.67
3
C13
H9
4
Methyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)penta-2,3-dienoate (2b). Yield 0.88 g (75%), white
crystals, mp 87-88 C. IR spectrum, сm-1: 1709, 1771, 1964. 1H NMR (CDCl3), δ ppm: 3.63 s (3Н, СН3);
4.36 m. (2H, CH2), 5.64 d.d. (1H, CH, J = 6.2, 2.9, 2.6 Hz), 5.74 m (1H, CH), 7.66-7.81 m (4Н, С6Н4). 13C
NMR (CDCl3), δ ppm: 35.09 (CH2), 52.11 (СH3), 90.43 (СНallene.), 91.40 (СНallene.), 123.39 (СНarom.),
131.91 (Сarom.), 134.15 (СНarom.), 165.36 (С=O), 167.39 (С=О), 212.37 (=С=). MS: m/z 258 [MH]+, 257
[M]-. Anal. Calcd for С14Н11NO4 (257.07): С 65.37; Н 4.31; N 5.44; O 24.88. Found: С 65.35; Н 4.29; N
5.44.
Methyl 6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)hexa-2,3-dienoate (2c). Yield 1.01 g (87%), white
crystals, mp 102-104 C. IR, сm-1: 1701, 1765, 1952. 1H NMR (CDCl3), δ ppm: 2.59 m (2H, CH2), 3.54 s
(3Н, СН3); 3.87 t (2H, CH2, J = 7 Hz), 5.52 m (1H, CH), 5.65 m (1H, CH), 7.68-7.83 m (4Н, С6Н4). 13C
NMR (CDCl3), δ ppm: 26.70 (CH2), 36.77 (CH2), 51.76 (СH3), 88.39 (СНallene.), 91.69 (СНallene.), 123.21
(СНarom.), 131.97 (Сarom.), 133.93 (СНarom.), 165.96 (С=O), 168.11 (С=О), 212.44 (=С=). MS: m/z 272
[MH]+, 271 [M]-. Anal. Calcd for С15Н13NO4 (271.27): С 66.41; Н 4.83; N 5.16; O 23.59. Found: С 66.39;
Н 4.81; N 5.16.
Methyl icosa-2,3-dienoate (2d). Yield 0.88 g (77%), yellow oil. IR, сm-1: 1724, 1961, 2852, 2922. 1H
NMR (CDCl3), δ ppm: 0.88 t (3Н, СН3, J = 7.2); 1.25 m (26Н, 13СН2), 1.63 m (2Н, СН2), 3.73 s (3Н, СН3),
4.45 m (2H, CH2), 5.57 m (1Н, =СН, J = 7.0), 5.63 d (1Н, =СН, J = 7.0). 13C NMR (CDCl3), δ ppm: 14.07
(СH3), 22.66 (СН2), 27.43 (СН2), 28.7 (СН2), 28.95 (СН2), 29.33 (СН2), 29.67 (9СН2), 31.91 (СН2), 51.83
(СН3), 87.7 (=СНallene), 95.44 (=СНallene), 167.2 (С=О), 212.41 (=С=). MS: m/z 323 [MH]+, 322 [M]-. Anal.
Calcd for С21Н38O2 (322.53): С 78.2; Н 11.88; O 9.92. Found: С 78.2; Н 11.88.
1
Methyl octadeca-2,3-dienoate (2e). Yield 0.98 g (85%), yellow oil. IR, сm-1: 1961, 61. H NMR
(CDCl3), δ ppm: 0.85 t (3Н, СН3, J = 6.7); 1.14-1.23 m (22Н, 2СН2), 1.38-1.46 m (2Н, СН2), 2.08-2.14 m
(2Н, СН2), 3.59 s (3Н, СН3), 5.53 s (1Н, =СН), 5.58 s (1H, =СН). 13C NMR (CDCl3), δ ppm: 14.8 (СH3),
22.62 (СН2), 25.74 (СН2), 28,64 (СН2), 28,79 (СН2), 28,91 (СН2), 29.09 (СН2), 29.3 (СН2), 29.48 (5СН2),
31.88 (СН2), 51,8 (OСН3), 87.85 (=СНalk), 95.45 (СН), 166.58 (С=О), 212.32 (=С=). MS: m/z 295 [MH]+,
294 [M]-. Anal. Calcd for С19Н34O2 (294.47): С 77.5; Н 11.64; O 10.87. Found: С 77.51; Н 11.65; O 10.84.
Methyl octa-2,3-dienoate (2f). Yield 0.88 g (66%), yellow oil. IR, сm-1: 1961, 61. 1H NMR (CDCl3), δ
ppm: 0.87 t (3Н, СН3, J = 6,5); 1.21-1.48 m (4Н, 2СН2), 2.15 m (2Н, СН2), 3.74 s (3Н, СН3), 5.64 s (1Н,
=СН), 6.55 s (1H, =СН). 13C NMR (CDCl3), δ ppm: 13.64 (СH3), 21.82 (СН2), 25.74 (СН2), 30.67 (СН2),