1868
NURKENOV et al.
7.2 Hz), 7.69 d (1Н, СНAr, JНН 8.9 Hz), 9.68 s [1Н,
С(О)Н]. Found, %: С 76.32; Н 8.15; N 7.45.
С12H15NO. Calculated, %: С 76.16; H 7.99; N 7.40.
СН=N), 11.85 br.s (1Н, NH). Found, %: C 65.84; H
5.97; N 18.10. C17H18N4O2. Calculated, %: C 65.79; H
5.85; N 18.05.
4-(N-Cytisinyl)benzaldehyde (III). Yield 42%,
mp 244–245°C. IR spectrum, ν, cm–1: 1674 (С=О),
1655 (С=О). 1Н NMR spectrum, δ, ppm: 1.96 br.t (2Н,
Н8), 2.57 br.s (1Н, Н9), 3.08 br. d (1Н, Н7, J 12.5 Hz),
3.15 d. d (1H, H11a, J11a,11e 12.3, J11a,9 2.2 Hz), 3.25 br.d
(1Н, Н13а, J13a,7 2.3 Hz), 3.72 d. d (1Н, Н10а, J10a,9 5.9,
J10a,10e 15.5 Hz), 3.94 d (1Н, Н10е, J10е,10а 15.4 Hz),
3.95 br.s (1Н, Н13е), 4.14 br.d (1Н, Н11е, J11е,11a
12.5 Hz), 6.15 d.d (1Н, Н3, J3,4 9.0, J3,5 1.3 Hz), 6.22
d.d (1Н, Н5, J5,4 6.9, J5,3 1.3 Hz), 6.91 d (2НAr, J
8.9 Hz), 7.32 d. d (1Н, Н4, J4,5 6.9, J4,3 9.0 Hz), 7.62 d
(2НAr, J 8.9 Hz), 9.66 s [1Н, С(О)Н]. Found, %: C
73.87; H 6.54; N 4.82. C18H18N2O2. Calculated, %: C
73.45; H 6.16; N 4.77.
N-[4-(Piperidin-1-yl)benzylidene]isonicotinylhyd-
razide (V). Yield 87%, mp 206–207°C. IR spectrum,
ν, cm–1: 1682 (С=О). 1Н NMR spectrum, δ, ppm: 1.60
br.s (6Н, СН2СН2СН2), 3.30 t (2Н, NСН2, JНН 5.4 Hz),
6.99 d (1Н, СНAr, JНН 6.4 Hz), 7.55 d (1Н, СНAr, JНН
8.8 Hz), 8.77 d (1Н, СН1, JНН 6.6 Hz), 7.81 d (1Н,
СН2), 8.35 s (1Н, СН=N), 11.82 br.s (1Н, NH). Found,
%: C 70.26; H 6.65; N 18.22. C17H18N4O2. Calculated,
%: C 70.11; H 6.54; N 18.17.
2-Hydroxy-N-(4-(piperidin-1-yl)benzylidene)-
benzohydrazide (VII). Yield 74%, mp 227–228°C. IR
1
spectrum, ν, cm–1: 1662 (C=O). H NMR spectrum, δ,
ppm: 1.58 br.s (6Н, СН2СН2СН2), 3.36 s (2Н, NСН2),
6.98 d (1Н, СНAr, JНН 6.8 Hz), 7.56 d (1Н, СНAr, JНН
8.8 Hz), 7.43 t (1Н, СН2Ar, JНН 6.9 Hz), 6.95 d (1Н,
СН3Ar, JНН 7.4 Hz), 7.90 d (1Н, СН4Ar, JНН 7.8 Hz), 8.33
s (1Н, СН=N), 11.67 br.s (1H, OH), 12.08 br.m (1Н,
NH). Found, %: C 70.59; H 6.61; N 13.22. C19H21N3O2.
Calculated, %: C 70.54; H 6.55; N 12.99.
General procedure for the synthesis of amino-
aldehydes I, III under microwave irradiation. To a
solution of 0.02 mol of 4-fluorobenzaldehyde in 15 mL
of DMF was added 0.022 mol of the appropriate amine
(morpholine or cytisine) and 0.025 g of potassium
carbonate. The reaction mixture was irradiated in a
microwave device LG MS2022G at irradiation power
of 500 W for 30 min with minor interruptions. Then to
the reaction mixture was added 100 mL of water, and
the product was extracted with ethyl acetate (3×60 mL).
The combined solutions were dried over anhydrous
Na2SO4 and evaporated to dryness. The resulting
precipitate was recrystallized from 2-propanol.
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General procedure for the synthesis of hyd-
razones IV–VII. To a solution of 0.003 mol of amino-
benzaldehyde I, III in 10 mL of ethanol was added
0.003 mol of the appropriate hydrazide (isonicotinyl-
hydrazine, salicylic acid hydrazide). The reaction mix-
ture was refluxed at 60–70°C for 2–2.5 h. The pre-
cipitate formed was filtered off, washed with ethanol,
dried, and recrystallized from 2-propanol.
N-(4-Morpholinobenzylidene)isonicotinylhydra-
zide (IV). Yield 80%, mp 256–257°C. IR spectrum, ν,
p. 1592.
9. Murray, J.K., J. Am. Chem. Soc., 2005, no. 127, p. 13271.
1
cm–1: 1680 (С=О). Н NMR spectrum, δ, ppm: 3.23 t
10. Kulakov, I.V., Turdybekov, D.M., Zhambekov, Z.M.,
Nurkenov, O.A., Ibragimov, B.T., Talipov, S.A., and
Turdybekov, K.M., Khim. Prirod. Soed., 2009, no. 5,
p. 572.
[4H, N(CH2)2, JНН 4.2 Hz], 3.74 t [4H, O(CH2)2, JНН
4.5 Hz], 7.02 d (1Н, СНarom, JНН 6.2 Hz), 7.61 d (1Н,
СНAr), 8.78 d (1Н, СН1), 7.80 d (1Н, СН2), 8.35 s (1Н,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 10 2013