428
PAN’KOV et al.
Phenyl imidazole-1-carboximidate (XXI). To
Compounds XIV XVI and XIX were synthesized
in a similar way.
a solution of 0.032 g (0.034 mmol) of freshly distilled
phenol in 3 ml of dry benzene we added 0.0004 g
(0.017 mmol) of sodium hydride. When evolution of
hydrogen ceased, we added to the resulting suspension
0.03 g (0.32 mmol) of 1-cyanoimidazole, and the
mixture was refluxed for 5 h. It was then cooled to
18 20 C and filtered, the filtrate was evaporated
under reduced pressure, the residue was dissolved in
2 ml of dry diethyl ether, 3 ml of petroleum ether was
1-Naphthyl imidazole-1-carboximidate (XII). To
a solution of 0.055 g (0.381 mmol) of 1-naphthol in
11 ml of dry benzene we added 0.036 g (0.381 mmol)
of 1-cyanoimidazole, and the mixture was heated for
5 h. Removal of the solvent left an oily substance
which was purified by flash chromatography.
Compounds XIII, XVII, XVIII, and XX were
synthesized in a similar way.
Yields, melting points or Rf values, spectral parameters, and elemental analyses of compounds XI XXIV
1
IR spectrum, , cm
Comp.
no.
Yield,
%
mp,
(Rf)a
C
1H NMR spectrum, , ppm
N H C N C N
XI
80
27
30
112 112.5
3325
3300
3340
1700
1690
1710
3.30 br.s (1H, NH), 6.72 d (2H, C6H4, J = 9.2 Hz), 6.97 s,
7.72 (2H, CH, imidazole), 7.90 d (2H, C6H4, J =
9.2 Hz), 8.32 s (1H, CH, imidazole)
4.95 br.s (1H, NH), 6.88 6.91 m (2H, C10H7), 7.24 7.34 m
(2H, C10H7), 7.38 7.47 m (3H, C10H7), 7.09 s, 7.76 s
(2H, CH, imidazole), 8.22 s (1H, CH, imidazole)
5.4 br.s (1H, NH), 7.12 7.19 m (3H, C10H7), 7.26 7.43 m
(4H, C10H7), 7.10 s, 7.75 s (2H, CH, imidazole), 8.20 s
(1H, CH, imidazole)
b
XII
XIII
(0.60)
b
(0.65)
XIV
XV
42
44
127 128
128.5 129
3315
3290
1710
1710
3.38 br.s (1H, NH), 7.07 s, 7.64 s (2H, CH, imidazole),
7.45 d (2H, C6H4, J = 8.2 Hz), 8.05 d (2H, C6H4, J =
8.2 Hz), 8.24 s (1H, CH, imidazole), 10.02 s (1H, CHO)
2.52 s (3H, CH3), 3.03 br.s (1H, NH), 6.94 d (2H, C6H4,
J = 9.2 Hz), 7.52 s, 8.33 s (2H, CH, imidazole), 8.12 d
(2H, C6H4, J 9.2 Hz)
2.35 s (3H, CH3), 3.04 br.s (1H, NH), 6.86 6.92 m (2H,
C10H7), 7.26 7.36 m (2H, C10H7), 7.40 7.50 m (3H,
C10H7), 7.82 d, 8.14 d (2H, CH, imidazole, J = 1.7 Hz)
2.36 s (3H, CH3), 3.37 br.s (1H, NH), 7.07 7.15 m (3H,
C10H7), 7.24 7.43 m (4H, C10H7), 7.73 d, 7.77 d (2H,
CH, imidazole, J = 1.7 Hz)
XVI
65
6
100 101
3300
3315
3330
1710
1690
1695
b
XVII
XVIII
(0.55)
b
12
(0.62)
XIX
XX
15
22
110 112
(0.26)
3240
3330
1700
1690
2.37 s (3H, CH3), 3.41 br.s (1H, NH), 6.92 d, 7.77 d (2H,
CH, imidazole, J = 1.8 Hz), 6.97 m, 7.72 m (4H, C6H4),
9.79 s (1H, CHO)
XXI
54
55
91
94
69.5 70.5
3240
3330
1710
1700
4.0 br.s (1H, NH), 7.15 7.29 m (5H, C6H5), 7.37 s, 7.68 s
(2H, CH, imidazole), 8.27 s (1H, CH, imidazole)
2.36 s (3H, CH3), 3.93 br.s (1H, NH), 6.74 6.87 m (5H,
C6H5), 7.15 d, 7.23 d (2H, CH, imidazole, J = 1.6 Hz)
2295 7.20 s, 8.00 s (2H, CH, imidazole), 8.50 s (1H, CH,
imidazole), 8.59 s (2H, C6H2), 9.04 br.s (1H, NH)c
2295 2.55 s (3H, CH3), 7.15 d, 7.90 d (2H, CH, imidazole, J =
1.7 Hz), 8.59 s (2H, C6H2), 9.38 br.s (1H, NH)c
b
XXII
XXIII
XXIV
(0.40)
115 116
109.5 110.5
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 3 2001