POLYFUNCTIONAL IMIDAZOLES: XII.
877
139.10 (Carom). Found, %: C 55.52; H 3.90; N 23.08.
m/z 302 [M + 1]+. C14H12ClN5O. Calculated, %:
C 55.73; H 4.01; N 23.21. M 301.74.
7.6 Hz), 7.47 d (2H, Harom, J = 8.0 Hz), 7.57 d (2H,
H
arom, J = 8.0 Hz), 7.93 s (1H, 2′-H). 13C NMR spec-
trum, δC, ppm: 20.44 (CH3), 41.68 (CH2), 58.66 (CH),
82.94 (CH), 121.04 (C5′), 133.70 (C4′), 137.13 (C2′),
126.33, 127.43, 128.75, 129.48, 129.59, 129.87,
134.25, 138.35 (Carom), 170.09 (C=O), 171.29 (C=O).
Found, %: C 55.52; H 3.43; N 18.58. m/z 456 [M + 1]+.
C21H16Cl2N6O2. Calculated, %: C 55.40; H 3.54;
N 18.46. M 455.31.
Compounds 7a–7f (general procedure). Azide 1a–
1c, 10 mmol, was dissolved in 10 mL of anhydrous
benzene, 10 mmol of N-arylmaleinimide 6a–6d was
added, and the mixture was refluxed for 2 h. The
solvent was removed under reduced pressure, and the
residue was purified by silica gel column chromatog-
raphy using hexane–ethyl acetate (4:1) as eluent.
1-{[4-Chloro-1-(4-methylphenyl)-1H-imidazol-
5-yl]methyl}-5-phenyl-3a,6a-dihydropyrrolo[3,4-d]-
[1,2,3]triazole-4,6(1H,5H)-dione (7d). Yield 81%,
mp 232–234°C. IR spectrum: ν 1710 cm–1 (C=O).
1H NMR spectrum, δ, ppm: 2.33 s (3H, CH3), 4.27 d
(1H, J = 10.8 Hz), 4.88 d (1H, J = 15.6 Hz), 4.94 d
(1H, J = 15.6 Hz), 5.64 d (1H, J = 10.8 Hz), 7.12 d
(2H, Harom, J = 7.6 Hz), 7.44 s (4H, Harom), 7.42–
7.53 m (3H, Harom), 7.86 s (1H, 2′-H). 13C NMR spec-
trum, δC, ppm: 20.74 (CH3), 41.83 (CH2), 59.28 (CH),
83.16 (CH), 121.13 (C5′), 132.99 (C4′), 137.28 (C2′),
125.65, 126.84, 128.84, 129.16, 129.67, 130.11,
131.54, 138.81 (Carom), 170.18 (C=O), 171.27 (C=O).
Found, %: C 47.92; H 3.20; N 19.78. m/z 421 [M + 1]+.
C21H17ClN6O2. Calculated, %: C 47.75; H 3.15;
N 19.89. M 420.86.
1-{[4-Chloro-1-(4-chlorophenyl)-1H-imidazol-
5-yl]methyl}-5-(4-chlorophenyl)-3a,6a-dihydropyr-
rolo[3,4-d][1,2,3]triazole-4,6(1H,5H)-dione (7a).
Yield 72%, mp >250°C. IR spectrum: ν 1715 cm–1
1
(C=O). H NMR spectrum, δ, ppm: 4.27 d (1H, J =
10.8 Hz), 4.91 d (1H, J = 15.6 Hz), 4.99 d (1H, J =
15.6 Hz), 5.65 d (1H, J = 10.8 Hz), 7.17 d (2H, Harom
,
J = 8.4 Hz), 7.47 d (2H, Harom, J = 8.4 Hz), 7.53–
7.59 m (4H, Harom), 7.93 s (1H, 2′-H). 13C NMR spec-
trum, δC, ppm: 41.62 (CH2), 58.69 (CH), 82.57 (CH),
121.61 (C5′), 133.27 (C4′), 137.14 (C2′), 127.57, 128.38,
128.99, 129.41, 129.87, 130.22, 133.72, 134.24
(Carom), 169.81 (C=O), 170.97 (C=O). Found, %:
C 50.23; H 2.80; N 17.50. m/z 476 [M + 1]+.
C20H13Cl3N6O2. Calculated, %: C 50.50; H 2.75;
N 17.67. M 475.72.
1-{[4-Chloro-1-(4-methylphenyl)-1H-imidazol-
5-yl]methyl}-5-(4-chlorophenyl)-3a,6a-dihydropyr-
rolo[3,4-d][1,2,3]triazole-4,6(1H,5H)-dione (7e).
Yield 74%, mp 248–250°C. IR spectrum: ν 1715 cm–1
5-(4-Bromophenyl)-1-{[4-chloro-1-(4-chloro-
phenyl)-1H-imidazol-5-yl]methyl}-3a,6a-dihydro-
pyrrolo[3,4-d][1,2,3]triazole-4,6(1H,5H)-dione (7b).
Yield 78%, mp >250°C. IR spectrum: ν 1715 cm–1
1
(C=O). H NMR spectrum, δ, ppm: 2.33 s (3H, CH3),
1
4.25 d (1H, J = 10.8 Hz), 4.88 d (1H, J = 16.0 Hz),
4.98 d (1H, J = 16.0 Hz), 5.64 d (1H, J = 10.8 Hz),
7.17 d (2H, Harom, J = 8.0 Hz), 7.30 s (4H, Harom),
7.58 d (2Harom, J = 8.0 Hz), 7.86 s (1H, 2′-H).
13C NMR spectrum, δC, ppm: 20.73 (CH3), 41.64
(CH2), 58.77 (CH), 82.84 (CH), 121.00 (C5′), 133.25
(C4′), 136.90 (C2′), 125.58, 128.44, 129.08, 129.52,
129.94, 130.25, 132.86, 138.68 (Carom), 169.85 (C=O),
170.54 (C=O). Found, %: C 55.52; H 3.44; N 18.58.
m/z 456 [M + 1]+. C21H16Cl2N6O2. Calculated, %:
C 55.40; H 3.54; N 18.46. M 455.31.
(C=O). H NMR spectrum, δ, ppm: 4.27 d (1H, J =
10.8 Hz), 4.90 d (1H, J = 15.2 Hz), 4.99 d (1H, J =
15.2 Hz), 5.65 d (1H, J = 10.8 Hz), 7.11 d (2H, Harom
J = 7.6 Hz), 7.47 d (2H, Harom, J = 7.8 Hz), 7.58 d (2H,
arom, J = 7.8 Hz), 7.71 d (2H, Harom, J = 7.6 Hz),
,
H
7.92 s (1H, 2′-H). 13C NMR spectrum, δC, ppm: 41.62
(CH2), 58.73 (CH), 82.89 (CH), 121.05 (C5′), 133.72
(C4′), 137.12 (C2′), 121.77, 127.77, 128.69, 129.47,
129.87, 130.66, 132.01, 134.23 (Carom), 169.76 (C=O),
170.92 (C=O). Found, %: C 45.99; H 2.61; N 16.28.
m/z 521 [M + 1]+. C20H13BrCl2N6O2. Calculated, %:
C 46.18; H 2.52; N 16.16. M 520.18.
1-{[4-Chloro-1-(4-methylphenyl)-1H-imidazol-
5-yl]methyl}-5-(4-methylphenyl)-3a,6a-dihydropyr-
rolo[3,4-d][1,2,3]triazole-4,6(1H,5H)-dione (7f).
Yield 72%, mp 218–220°C. IR spectrum: ν 1715 cm–1
1-{[4-Chloro-1-(4-chlorophenyl)-1H-imidazol-
5-yl]methyl}-5-(4-methylphenyl)-3a,6a-dihydro-
pyrrolo[3,4-d][1,2,3]triazole-4,6(1H,5H)-dione (7c).
Yield 75%, mp 202–204°C. IR spectrum: ν 1715 cm–1
1
(C=O). H NMR spectrum, δ, ppm: 2.33 s (6H, CH3),
1
(C=O). H NMR spectrum, δ, ppm: 2.33 s (3H, CH3),
4.23 d (1H, J = 10.8 Hz), 4.87 d (1H, J = 15.6 Hz),
4.97 d (1H, J = 15.6 Hz), 5.62 d (1H, J = 10.8 Hz),
6.98 d (2H, Harom, J = 8.0 Hz), 7.26–7.31 m (6H,
7.23 d (1H, J = 10.8 Hz), 4.90 d (1H, J = 15.6 Hz),
5.01 d (1H, J = 15.6 Hz), 5.64 d (1H, J = 10.8 Hz),
6.98 d (2H, Harom, J = 7.6 Hz), 7.29 d (2H, Harom, J =
H
arom), 7.85 s (1H, 2′-H). 13C NMR spectrum, δC, ppm:
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 6 2016