768
TSAO et al.
(8H, Harom). Mass spectrum, m/z: 337 [M+]. Found, %:
EXPERIMENTAL
C 60.32; H 3.21; N 12.58. C17H11N3O5. Calculated, %:
C 60.54; H 3.29; N 12.45.
The IR spectra were recorded on a Bruker FT-IR
EQUINOX-55 spectrometer in KBr. The H NMR
1
3-(2-Phenyl-1,2,3-triazol-4-ylcarbonylhydrazono-
spectra were obtained on a Bruker AX-200 instrument
(200 MHz) using CDCl3 or DMSO-d6 as solvent and
TMS as internal reference. The mass spectra were run
on an HP-5988 mass spectrometer. TLC analysis was
performed on GF-254 plates. The melting points were
determined using an MP-S3 heating assembly (Japan).
The elemental compositions were determined with the
aid of an MT-3 automatic analyzer.
methyl)chromone (IIe). Yield 54%, mp 250 251.5 C.
1
IR spectrum, , cm : 3251 (NH), 3043 (C Harom),
1
1636 (C=O), 1617 (C=N), 1097 (C O C). H NMR
spectrum, , ppm: 9.83 br.s (1H, NH), 8.35 s (1H,
2-H), 8.20 s (1H, 5-H, triazole), 7.25 8.03 m (10H,
H
arom). Mass spectrum, m/z: 359 [M+]. Found, %: C
64.19; H 3.69; N 19.79. C19H13N5O3. Calculated, %:
C 63.51; H 3.65; N 19.49.
Aroylhydrazones IIa IIi (general procedure).
Equimolar amounts of compound I and appropriate
aroylhydrazone (prepared by the known procedure [4])
were dissolved in 95% alcohol, several drops of
glacial acetic acid were added, and the mixture was
refluxed for 5 6 h. After cooling, the precipitate was
filtered off and recrystallized from anhydrous alcohol.
3-(2-Trifluoromethyl-1-benzimidazolylacetylhy-
drazonomethyl)chromone (IIf). Yield 85%, mp 225
1
227 C. IR spectrum, , cm : 3220 (NH), 2994
(C Harom), 1698 (C=O), 1639 (C=N), 1119 (C O C).
1H NMR spectrum, , ppm: 9.32 br.s (1H, NH),
8.58 s (1H, 2-H), 8.31 d (1H, CH=N), 7.24 7.92 m
(8H, Harom), 5.94 s (2H, CH2). Mass spectrum, m/z:
414 [M+]. Found, %: C 57.95; H 3.20; N 13.63.
C20H13F3N4O3. Calculated, %: C 57.98; H 3.16;
N 13.52.
3-(Benzoylhydrazonomethyl)chromone (IIa).
1
Yield 78%, mp 176 178 C. IR spectrum, , cm :
3280 (NH), 3076 (S Harom), 1679 (C=O), 1636
1
(C=N), 1070 (C O C). H NMR spectrum, , ppm:
3-(1-Benzotriazolylacetylhydrazonomethyl)chro-
10.21 br.s (1H, NH), 8.87 s (1H, 2-H), 7.24 7.98 m
(10H, CH=N, Harom). Mass spectrum, m/z: 292 [M+].
Found, %: C 70.31; H 4.19; N 9.68. C17H12N2O3.
Calculated, %: C 69.86; H 4.14; N 9.58.
mone (IIg). Yield 61%, mp 240 241 C. IR spectrum,
1
, cm : 3219 (NH), 2990 (C Harom), 1698 (C=O),
1
1640 (C=N), 1109 (C O C). H NMR spectrum, ,
ppm: 9.63 br.s (1H, NH), 8.52 s (1H, 2-H), 8.30 d
(1H, CH=N), 7.23 7.86 m (8H, Harom), 5.52 s (2H,
3-(o-Chlorobenzoylhydrazonomethyl)chromone
(IIb). Yield 80%, mp 193 195 C. IR spectrum,
,
CH2). Mass spectrum, m/z: 347 [M+]. Found, %: C
62.20; H 3.80; N 20.21. C18H13N5O3. Calculated, %:
C 62.25; H 3.77; N 20.16.
1
cm : 3230 (NH), 3059 (C Harom), 1674 (C=O),
1
1633 (C=N), 1059 (C O C), 656 (C Cl). H NMR
spectrum, , ppm: 10.15 br.s (1H, NH), 8.77 s (1H,
2-H), 7.23 7.92 m (9H, CH=N, Harom). Mass spec-
trum, m/z: 328, 326 [M+]. Found, %: C 61.89; H 3.41;
N 8.67. C17H11ClN2O3. Calculated, %: C 62.49;
H 3.39; N 8.57.
3-(Nicotinoylhydrazonomethyl)chromone (IIh).
Yield 90%, mp 214 216 C. IR spectrum, , cm :
1
3262 (NH), 3093 (C Harom), 1682 (C=O), 1648 (C=N),
1
1046 (C O C). H NMR spectrum, , ppm: 9.96 br.s
(1H, NH), 8.92 and 8.81 (2H, 2-H and 5-H, pyridine),
8.2 s (1H, 2-H), 7.33 7.74 m (7H, CH=N, Harom, 4-H,
pyridine). Mass spectrum, m/z: 293 [M+]. Found, %:
C 66.04; H 3.83; N 14.53. C16H11N3O3. Calculated, %:
C 65.53; H 3.78; N 14.33.
3-(o-Nitrobenzoylhydrazonomethyl)chromone
(IIc). Yield 95%, mp 206 207 C. IR spectrum,
,
1
cm : 3267 (NH); 3079 (C Harom); 1666 (C=O); 1633
1
(C=N); 1520, 1341 (NO2); 1071 (C O C). H NMR
spectrum, , ppm: 9.74 br.s (1H, NH), 8.70 s (1H,
2-H), 8.42 d (1H, CH=N), 7.23 7.92 m (8H, Harom).
Mass spectrum, m/z: 337 [M+]. Found, %: C 60.63;
H 3.31; N 12.40. C17H11N3O5. Calculated, %: C 60.54;
H 3.29; N 12.46.
3-(5-Methyl-1-phenyl-1,2,3-triazol-4-ylcarbonyl-
hydrazonomethyl)chromone (IIi). Yield 92%, mp
1
223.5 225 C. IR spectrum, , cm : 3240 (NH), 3069
(C Harom), 1677 (C=O), 1641 (C=N), 1059 (C O C).
1H NMR spectrum, , ppm: 8.82 br.s (1H, NH), 8.5 s
(1H, 2-H), 8.25 d (1H, CH=N), 7.56 7.26 m (9H,
3-(p-Nitrobenzoylhydrazonomethyl)chromone
H
arom), 2.69 s (3H, CH3). Mass spectrum, m/z:
(IId). Yield 90%, mp 230 232 C. IR spectrum,
,
373 [M+]. Found, %: C 64.56; H 3.98; N 18.82.
1
cm : 3260 (NH); 3071 (C Harom); 1670 (C=O); 1636
(C=N); 1498, 1319 (NO2); 1518, 1338 (C O C).
1H NMR spectrum, , ppm: 9.72 br.s (1H, NH),
8.76 s (1H, 2-H), 8.47 d (1H, CH=N), 7.25 7.89 m
C20H15N5O3. Calculated, %: C 64.34; H 4.05; N 18.76.
3-(2-Aryl-1,3,4-oxadiazol-5-yl)chromones IIIa
IIIi (general procedure). A solution of 2.2 mmol of
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 5 2001