Unexpected formation of ethyl 5-cyano-6-[cyano(4′-phenyl-1,3′- selenazol-2-yl)methyl]-4-(furan-2′-yl)-2-methyl-1,4-dihydropyridine-3- carboxylate

Full text of DOI:10.1134/S1070363211020332

ISSN 1070-3632, Russian Journal of General Chemistry, 2011, Vol. 81, No. 2, pp. 442–443. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © V.D. Dyachenko, S.V. Roman, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 2, pp. 344–345.
LETTERS
TO THE EDITOR
Unexpected Formation of Ethyl 5-Cyano-6-[cyano(4'-phenyl-
1,3'-selenazol-2-yl)methyl]-4-(furan-2'-yl)-2-methyl-
1,4-dihydropyridine-3-carboxylate
V. D. Dyachenko and S. V. Roman
Taras Shevchenko Lugansk National University, Oboronnaya ul. 2, Lugansk, 91011 Ukraine
е-mail: dvd_lug@online.lg.ua
Received April 27, 2010
DOI: 10.1134/S1070363211020332
2-Furfurylidene acetoacetic ester I condensed with
cyanoselenoacetamide II in the presence of N-
methylmorpholine to give N-methylmorpholinium 6-
methyl-4-(fur-2'-yl)-3-cyano-5-ethoxycarbonyl-1,4-
dihydropyridine-2-selenolate [1].
pyridine-3-carboxylate (IV). To a stirred solution of
1.04 g (5 mmol) of furfurylidene acetoacetic ester I in
20 ml of anhydrous ethanol was added 1.47 g
(10 mmol) of cyanoselenoacetamide II and 1.05 ml
(10 mmol) of N-methylmorpholine at 20°С under
argon atmosphere. The reaction mixture was stirred for
10 min, then 1.0 g (5 mmol) of phenacyl bromide III
was added, and the mixture was stirred for 30 min and
left standing. After 2 days it was diluted with equal
volume of water. The resin obtained was decanted,
washed with water, and recrystallized from АсОН.
Yield 1.71 g (68%), mp 203–205°С. IR spectrum, ν,
Involving an alkyl halide into this condensation
opens a way to the previously unknown 7-alkylseleno-
5-amino-2-methyl-4-(fur-2'-yl)-8-cyano-3-ethoxycar-
bonyl-1,4-dihydro-1,6-naphthyridines [2].
We found for the first time that the reactions of 2-
furfurylidene acetoacetic ester I with cyanoseleno-
acetamide II, phenacyl bromide III, and N-methyl-
morpholine afforded ethyl 2-methyl-4-(fur-2'-yl)-5-
cyano-6-[cyano(4'-phenyl-1',3'-selenazol-2'-yl)methyl]-
1,4-dihydropiridine-3-carboxylate IV.
1
cm–1: 3302 (NH), 2175, 2250 (C≡N), 1700 (С=О). Н
NMR spectrum, δ, ppm: 1.31 t (3Н, СН3, J 6.19 Hz),
2.68 s (3Н, 3СН3), 4.23 q (2Н, ОСН2, J 6.19 Hz), 4.66
s (1Н, CH), 4.73 s (1Н, CH), 6.17 d (1Н, Н3, furyl, J
2.94 Hz), 6.32 d.d (1Н, Н4, furyl, J 2.41 Hz), 7.32–
7.51 m (4Н, Рh and Н5, furyl), 7.89 d (2Н, Рh, J
7.02 Hz), 8.59 s (1Н, Н5, selenazolyl), 12.24 br.s (1H,
NH). Mass spectrum (EI, 70 eV), m/z (Irel, %): 504
(19) [M + 1]+, 503 (8) [M]+, 475 (7), 423 (28), 398 (7),
182 (44), 158 (19), 102 (100), 89 (18), 81 (52), 63
We are studying the applicability of this reaction,
its mechanism and chemical-biological properties of
compound IV.
Ethyl 2-methyl-4-(furfur-2'-yl)-5-cyano-6-[cyano-
(4'-phenyl-1',3'-selenazol-2'-yl)methyl]-1,4-dihydro-
O
O
O
NCH3
O
CN
Se
O
O
CN
CN
+
+
H3C
O
−H2O,
−HBr
H3C
O
N
Br
H2N
H3C
N
H3C
O
Se
H
IV
I
II
III
442

UNEXPECTED FORMATION OF ETHYL 5-CYANO-6-[CYANO(4'-PHENYL-...
443
(17), 51 (14), 39 (26). Found, %: С 59.51; Н 3.88;
N 11.02. C25H20N4О3Sе. Calculated, %: С 59.65;
Н 4.00; N 11.13.
The IR spectrum was recorded on a IKS-29 spectro-
photometer in mineral oil.
REFERENCES
1
The Н NMR spectrum was registered on a Bruker
1. Dyachenko, V.D. and Sharanin, Yu.A., Zh. Obshch.
Khim., 1991, vol. 61, no. 4, p. 948.
2. Dyachenko, V.D., Roman, S.V., and Litvinov, V.P., Izv.
Akad. Nauk, Ser. Khim., 2000, no. 1, p. 121.
AM-300 instrument (300.13 MHz) in DMSO-d6
relative to internal TMS. The mass spectrum was
measured on a Kratos MS-890 spectrometer (70 eV)
using a direct injection of a sample into the ion source.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 2 2011