SYNTHESIS OF FUNCTIONALLY SUBSTITUTED
1291
NMR spectroscopy and chromato-mass-spectrometry
data (see table).
reaction mixture was cooled to 0–5°C. The desired
products were filtered through a glass porous filter,
washed with cold methanol, and dried in air for 6–8 h.
In the IR spectra of 2,2'-arylmethylenebis(3-hyd-
–
1
roxy-5,5-dimethylcyclohex-2-enones)
XVII–XXII,
Compound XXV. IR spectrum, ν, cm : 3131
(CH ); 3061, 3043 (CH ); 2959, 2931, 2888,
XXV–XXX, XXXII, XXXV, XXXVI characteristic
isoxazole
Ar
absorption bands were observed of СH (3081, 3059,
2872 (СН ); 1594 (С=О); 1619, 1579, 1499
Ar
aliph
–
1
3
2
023, 776, 721, 695 cm ), СН
(2962, 2930,
(С=С ); 1450 (С=N
); 1262, 1231, 1139,
aliph
Ar
isoxazole
–
1
–1
872 cm ), C=O
(1765–1720 cm ), C=C–C=O
1040, 1008 (С–О); 896, 870, 848, 810, 764, 740, 724
ester
–
1
1
and С=С (1595, 1510 and 1375 cm ), C–O (1275–
(CH ). Н NMR spectrum, δ, ppm: 1.14 s (12Н, 4Ме),
Ar
Ar
–
1
1
010 cm ) and no absorption band of C=O of the
2.38 s (8H, 4СН ), 5.41 s (1H, CH), 6.17 s (1H,
2
–
1
3
starting aldehydes at 1695–1680 cm [1, 7]. The IR
CH
), 7.40 m (3Н ), 7.70 d (2Н , J 8 Hz),
isoxazole
Ar
Ar
1
3
spectra of xanthenes XXXVII, XXXVIII contain
12.23 br.s (2Н, ОН). С NMR spectrum, δ , ppm:
С
–
1
characteristic absorption bands of СH (3054 cm ),
27.99 (Me), 46.59 (СН ), 99.31 (СН
); 125.83,
carb
2
isoxazole
–1
СH (3070, 3059, 3004, 842, 820, 760, 684, 570 cm ),
128.92, 130.07 (СН ); 31.53, 114.12, 127.53, 163.07,
Ar
Ar
–
1
СН
(2958, 2946, 2835, 2873, 2830 cm ), C=O
169.66 (С ); 189.91 (С=О).
aliph
ester
tert
–
1
(
1
1
1760–1758 cm ), C=C–C=O and С=С (1680, 1666,
–1
Ar
Compound XXVI. IR spectrum, ν, cm : 3134
isoxazole
–
1
626, 1606, 1508, 1376 cm ) and C–O (1360, 1277,
–1
(
CH
); 3087, 3058, 3034 (CH ); 2959, 2929,
Ar
252, 1195, 1165, 1123, 1032, 995 cm ).
2
888, 2871 (СН ); 1592 (С=О); 1615, 1511, 1468
aliph
1
13
In the H and C NMR spectra of VI, VII, XVII–
(С=С ); 1451 (С=N
); 1262, 1231, 1139,
Ar
isoxazole
XXII, XXV–XXX, XXXII, XXXV, XXXVI,
XXXVII, XXXVIII there are signals of all the struc-
tural fragments (aromatic, carborane, isoxazole, ester
group) [1, 7].
1040, 1008 (С–О); 896, 870, 848, 810, 764, 740, 724
1
(CH ).
Н
NMR spectrum, δ, ppm: 1.14
s
Ar
(12Н, Ме), 2.34 s (3Н, МеC H ), 2.37 s (8H, 4СН ),
6
4
2
5.39 s (1H, CH), 6.12 s (1H, CHisoxazole), 7.19 d (2НAr
,
3
1
3
J 8 Hz), 7.58 d (2Н , J 8 Hz), 12.24 br.s (2Н, ОН).
Ar
The synthesized compounds contain pharma-
cophore fragments. They will be screened for the bio-
logical activity to establish a link between their
structure and pharmacological activity and to create
new drugs [10–13] and agents for boron neutron
capture therapy of cancer [14, 15].
3
С NMR spectrum, δ , ppm: 21.49 (МеC H ), 27.94
С
6
4
(
(
(
Me), 46.54 (СН ), 98.67 (СН
); 125.72, 129.55
2
isoxazole
СН ); 31.48, 114.10, 124.82, 140.23, 163.07, 169.66
Ar
С ); 189.83 (С=О).
tert
Xanthenes XXXVII, XXXVIII. A mixture of
.01 mol of XVIII or XXII, 0.5 g of sulfocationite
0
EXPERIMENTAL
FIBAN K-1, and 75 mL of benzene was refluxed with
a Dean–Stark trap for 16–18 h. Next, sulfocationite
was separated, and the solvent was removed. The
target compound was purified by column chromato-
graphy on Al O (60–100 µm, neutral, II Brockmann
IR spectra were recorded on a Nicolet Protégé-460
1
FTIR spectrophotometer from KBr pellets. H NMR
spectra were registered on a Tesla BS-587A spec-
trometer (100 MHz), internal reference TMS, chloro-
2
3
activity) eluting with benzene.
form-d as a solvent. Mass spectra were obtained on a
1
Hewlett Packard 5890/5972 instrument in the electron
impact ionization mode with ionizing electrons energy
of 70 eV (capillary column HP-5MS, 30 m × 0.25 mm,
stationary phase 5% PhMe Silicone, 0.25 µm, eva-
porator temperature 250°C).
REFERENCES
1. Dikusar, E.A., Potkin, V.I., and Kozlov, N.G.,
Benzaldegidy vanilinovogo ryada. Sintez proizvodnykh,
primenenie, i biologicheskaya aktivnost’ (Benzaldehydes
of Vaniline Series. Synthesis of Derivatives, Use and
Biological Activity), Saarbrücken: LAP LAMBERT
Academic Publishing GmbH & Co. KG, 2012.
2
,2'-Arylmethylenebis(3-hydroxy-5,5-dimethyl-
cyclohex-2-enones) (XVII–XXII, XXV–XXX, XXXII,
XXXV, XXXVI). A mixture of 0.01 mol of aldehyde
XI–XVI, XXIII, XXIV or 0.005 mol of dialdehyde
VI–IX, XXXI, XXXIII–XXXIV, 0.02 mol of di-
medone X, 0.1 g of triethylamine, and 50 mL of an-
hydrous methanol was refluxed for 1 h. Then the
2
. Semenov, A.A. and Kartsev, V.G., Biologicheskaya
aktivnost’ prirodnykh soedinenii (The Biological
Activity of Natural Compounds), Moscow: ICSPF, 2012.
3. Pershine, L.A. and Efanov, M.V., Khim. Rast. Syr’ya,
1997, no. 2, p. 42.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 7 2014