Reaction of cyanoselenoacetamide with 1,3-dicarbonyl compound anilinomethylene derivatives

Article abstract of DOI:10.1007/s10593-013-1379-x

The reaction of cyanoselenoacetamide with a 2-anilinomethylene derivative of Meldrum's acid (2 equiv. KOH, EtOH, 20 C) gives the 5-cyano-6-hydroseleno-2- oxo-1,2-dihydropyridine-3-carboxylic acid dipotassium salt. The latter reacts with alkyl halides to yield 5-cyano-6-(R-methylseleno)-2-oxo-1,2- dihydropyridine-3-carboxylic acids. Treatment of cyanoselenoacetamide with 2-anilinomethyl derivatives of dimedone and 1,3-cyclohexanedione is accompanied by oxidation and gives 2,2'-di-selane-1,2-diylbis(5-oxo-5,6,7,8- tetrahydroquinoline-3-carbonitriles). The obtained diselanes undergo cleavage using alkyl halides in KOH to give 2-(R-methylseleno)-5-oxo-5,6,7,8- tetrahydroquinoline-3-carbonitriles or selenopheno[2,3-b]quinolines as Thorpe-Ziegler cyclization products of the latter in low yields.

Full text of DOI:10.1007/s10593-013-1379-x

Chemistry of Heterocyclic Compounds, Vol. 49, No. 9, December, 2013 (Russian Original Vol. 49, No. 9, September, 2013)
REACTION OF CYANOSELENOACETAMIDE WITH
1,3-DICARBONYL COMPOUND ANILINOMETHYLENE
DERIVATIVES
K. A. Frolov1, V. V. Dotsenko1*, and S. G. Krivokolysko1
The reaction of cyanoselenoacetamide with a 2-anilinomethylene derivative of Meldrum's acid (2 equiv.
KOH, EtOH, 20ºC) gives the 5-cyano-6-hydroseleno-2-oxo-1,2-dihydropyridine-3-carboxylic acid
dipotassium salt. The latter reacts with alkyl halides to yield 5-cyano-6-(R-methylseleno)-2-oxo-
1,2-dihydropyridine-3-carboxylic acids. Treatment of cyanoselenoacetamide with 2-anilinomethyl
derivatives of dimedone and 1,3-cyclohexanedione is accompanied by oxidation and gives 2,2'-di-
selane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles). The obtained diselanes undergo
cleavage using alkyl halides in KOH to give 2-(R-methylseleno)-5-oxo-5,6,7,8-tetrahydroquinoline-
3-carbonitriles or selenopheno[2,3-b]quinolines as Thorpe–Ziegler cyclization products of the latter in
low yields.
Keywords: cyanoselenoacetamide, 1,2-dihydropyridine-3-carboxylic acid, enaminodicarbonyl compounds,
Meldrum's acid, selenoorganic compounds, Thorpe–Ziegler reaction, vinyl substitution.
Reaction of activated methylene compounds with 2-aminomethylene-1,3-dicarbonyl compounds as
1,3-bis-electrophilic 3C-synthons is a very popular method for the synthesis of various azines (for reviews, see
[1-8]). Amongst the most readily available enaminodicarbonyl substrates of this type are the 2-anilino-
methylene derivatives of 1,3-dicarbonyl compounds which are readily synthesized through a three-component
condensation of an activated methylene compound, triethylorthoformate, and aniline [9-13].
As shown previously [13-15], the reaction of the enaminodicarbonyl compounds 1, 4, 5 with the
activated methylene thioamides 2 and 8 occurs under mild conditions and is an efficient method for the
preparation of the pyridine-3-carboxylic acid 3, the quinolines 6, 7, and the pyrimidine-5-carboxamides 9.
O
O
NHPh
CN
1) KOH, EtOH;
2) HCl
CN
SH
S
HO
O
+
Me
[13]
NH2
O
N
O
1
O
2
H
Me
3
_______
*To whom correspondence should be addressed, e-mail: victor_dotsenko@bigmir.net.
1"ChemEx" Laboratory, Vladimir Dal' East Ukrainian National University, 20-A Molodyozhnyi Kv., Luhansk
91034, Ukraine.
_________________________________________________________________________________________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1397-1403, September, 2013.
Original article submitted June 4, 2013.
0009-3122/13/4909-1301©2013 Springer Science+Business Media New York
1301

O
O
NHPh
O
1) KOH, EtOH;
2) HCl
CN
S
+
2
R
R
O
[13]
N
H
R
R
4 (R = H)
5 (R = Me)
6 (R = H)
7 (R = Me)
NHR
1) KOH, EtOH;
2) HCl
O
N
H2N
S
O
1, 4, 5
+
[14, 15]
NHR
N
H
NHR
8
S
9
The practical significance of these compounds is due to the fact that they serve as starting materials for
the preparation of a number of biologically active compounds. These include group I metabotropic glutamate
receptor (mGluR1) modulators [16], IKK- inhibitors [17], ubiquitin C-terminal hydrolase L1 inhibitors [18],
HIV-1 integrase inhibitors [19], phosphodiesterase PDE4B inhibitors [20], etc.
Continuing our studies on the chemistry of cyanoselenoacetamide (10) [21] we have investigated the
reaction of the latter with the enaminodicarbonyl compounds 1, 4, 5. It was found that the selenoamide 10
readily reacts with the Meldrum's acid derivative 1 in the presence of 2 equivalents of KOH. Vinyl substitution
and subsequent heterocyclization gave the 5-cyano-6-hydroseleno-2-oxo-1,2-dihydropyridine-3-carboxylic acid
dipotassium salt 11 in 77% yield. When treated with alkyl halides the salt 11 is alkylated at the selenium atom
to give the corresponding dihydropyridine-3-carboxylic acids 12a-c in 30-57% yields.
H2N
Se
KOH, EtOH, Ar
20°C, 5–10 min
2–3°C, 24 h
CN
CN
O
Se
1
+
O
–Me2CO
–CO2
–PhNH2
NH2
O
O
10
Me
Me
Se
O
2K+
RCH2Hal
EtOH, H2O
CN
NC
NH
HO
room temp., 24 h
O
O
N
H
SeCH2R
12a–c
O
O
11
12 a R = CH=СН2, b R = СО2Et, c R = СОNHPh
The IR spectrum of compound 11 showed a strong absorption band corresponding to the stretching vibration
of the conjugated cyano group at 2220 cm-1 and a broad absorption band with a shoulder at 1710-1620 cm-1
corresponding to the carbonyl group. The N–H stretching vibrational bands occurred at 3391 and 3152 cm-1.
The IR spectra of compounds 12a-c contained a strong absorption band for the conjugated nitrile group at
1
2221-2190 cm-1 and a broad band in the range 1725-1710 cm-1 for the C=O group. The H NMR spectrum of
compound 11 showed a single signal for the H-4 proton at 7.97 ppm. The signal for the NH proton was absent
likely due to deuterium exchange. The 1H NMR spectra of compounds 12a-c contained the H-4 proton singlets
in the range of 7.91-8.30 ppm. The 1H NMR spectra of compounds 12a,b contained a rather characteristic signal
for the carboxyl group proton which was observed at very low field (17.40-17.53 ppm).
1302

Reaction of cyanoselenoacetamide (10) with the enaminodiketones 4 and 5 had a series of characteristic
features. In place of the quinoline-2-selenones 13 (as the quinolines 6 and 7 analogs) we only isolated their
oxidation products, namely, the corresponding 2,2'-diselane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-
3-carbonitriles) 14a,b in high (86-89%) yields. The tendency of the 3-cyanopyridine-2(1H)-selenones and
corresponding selenolates to readily undergo oxidation to diselanes in solution is well known [21]. It has been
noted that oxidation occurs even under an argon atmosphere in the presence of trace amounts of atmospheric
oxygen. It is has been suggested that the separation of the dipotassium salt 11 relates to its low solubility in
alcohol since the more soluble selenones 13 (or intermediately formed selenolates 15) undergo oxidation by
trace amounts of air in the reaction solution. The obtained diselanes 14a,b undergo cleavage under the action of
alkyl halides and 1 equivalent of KOH under mild conditions to give the quinoline 16 in 31% yield. In case
where the R1 substituent is a strong electron withdrawing group the alkylation is followed by a spontaneous
Thorpe–Ziegler cyclization to give the selenopheno[2,3-b]pyridines 17a-d in 24-52% yields.
H2N
Se
Se
N
NC
KOH, EtOH
20°C, 5 min
2–3°C, 12 h
K+
CN
O
4 or 5
+
10
O
–PhNH2
O
R
R
R
R
15a,b
O
R
O
O
CN
CN
N
R
HCl
[O]
Se
R
Se
R
N
Se
N
H
R
NC
R
14a,b
13a,b
O
O
NH2
R1CH2Hal, KOH
EtOH, H2O
CN
Se
R1
;
Me
R
, 1–2 min
room temp., 48 h
Se
CO2Me
N
N
Me
R
16 (from 14b)
17a–d
13–15 a R = H; b R = Me; 17 a R = H, R1 = 4-MeC6H4СО; b R = H, R1 = PhСО;
c R = Me, R1 = 4-MeC6H4СО; d R = Me, R1 = PhСО
The structure of the obtained quinolines 14a,b, 16, and 17a-d was confirmed by spectroscopic studies
and elemental analysis. Hence, the IR spectra of the diselanes 14a,b show the presence of absorption bands
corresponding to the stretching vibration of the conjugated cyano group at 2227-2222 cm-1 and strong bands for
the stretching of the C=O group at 1710-1650 cm-1. In turn, the IR spectrum of compound 16 shows an
absorption for the conjugated cyano group at 2225 cm-1 and two broad C=O group absorption bands at 1691 and
1740 cm-1. In the IR spectra of compounds 17a-d the bands corresponding to conjugated nitriles are absent but
absorptions are seen at 3390-3175 cm-1 (N–H) and 1725-1676 cm-1 (C=O). The 1H NMR spectra of compounds
14a,b, 16, and 17a-d show characteristic narrow singlets for the H-4 protons at 8.09-9.12 ppm. The mass
spectra of compounds 14a,b show peaks for the [M+H]+ ions with m/z 557 and 501, respectively.
Thus, the reaction of cyanoselenoacetamide with 1,3-dicarbonyl compound 2-anilinomethylene
derivatives opens up possibilities for the preparation of a series of novel pyridine and quinoline derived
selenium-containing compounds as structural analogs of biologically active substances.
1303

EXPERIMENTAL
IR spectra were recorded on an IRS-29 (LOMO) spectrophotometer using vaseline oil. 1H NMR spectra
were recorded on a Bruker DRX-400 instrument (400 MHz) using DMSO-d6 with TMS as internal standard.
APT 13C NMR spectra were recorded on a Bruker Avance 500 (126 MHz) also using DMSO-d6 and with TMS
as internal standard. Elemental analysis was performed on a Carlo-Erba 1106 Elemental Analyzer. HPLC-MS
Analysis was carried out on a Shimadzu LC-10AD liquid chromatograph with Shimadzu SP D-10A UV-Vis
(254 nm) and Sedex 75 ELSD detectors linked with a PE SCIEX API 150EX mass spectrometer using
electrospray ionization at atmospheric pressure. Melting points were determined on a Kofler heating bench and
are not corrected. Monitoring of the purity of the synthesized products was carried out by TLC on Silufol
UV-254 plates using acetone–hexane (1:1) as eluent and visualized using iodine vapor and a UV detector. The
starting cyanoselenoacetamide (10) was obtained by passing hydrogen selenide through an ether solution of
malononitrile in the presence of catalytic amounts of Et3N [22]. All of the operations were carried out under an
argon atmosphere (99.995% purity).
5-Cyano-6-hydroseleno-2-oxo-1,2-dihydropyridine-3-carboxylic Acid Dipotassium Salt (11).
Cyanoselenoacetamide 10 (1.00 gm, 6.8 mmol), 2,2-dimethyl-5-phenylaminomethylene-1,3-dioxane-4,6-dione 1
(1.68 g, 6.8 mmol), and 96% EtOH (30 ml) were placed in a flat-bottomed flask of volume 100 ml. The mixture
was stirred for 5 min at room temperature, and KOH (0.76 g, 13.6 mmol) was added. The flask was sealed, and
the mixture was stirred to dissolution of the starting reagents (5-10 min) and left for 24 h in a fridge (2-3ºC)
under an argon atmosphere. The precipitate formed was filtered off and washed with EtOH and acetone. The
obtained compound 11 was used in subsequent reactions without further purification. Yield 1.67 g (77%), finely
crystalline, yellow-green powder, mp ˃300ºC (decomp.). IR spectrum, , cm-1: 3391, 3152 (N–H), 2220 (C≡N),
1
1710-1620 (2С=О). Н NMR spectrum, , ppm: 7.97 (1Н, s, Н-4). Found, %: C 26.60; H 0.77; N 8.52.
C7H2K2N2О3Se. Calculated, %: C 26.33; H 0.63; N 8.77.
6-Alkylseleno-5-cyano-2-oxo-1,2-dihydropyridine-3-carboxylic Acids (12a-c) (General Method). A
mixture of salt 11 (150 mg, 0.47 mmol) and 70% EtOH (10 ml) was stirred to full dissolution of the salt. The
obtained solution was added through a fluted filter under an argon stream to a corresponding alkyl halide
(0.5 mmol) solution in 70% EtOH (10 ml). The mixture formed was stirred for 10 min and left for 24 h at room
temperature under an argon atmosphere. The precipitate formed was filtered off and washed with 70% EtOH.
6-(Allylseleno)-5-cyano-2-oxo-1,2-dihydropyridine-3-carboxylic Acid (12a). Yield 40 mg (30%),
fine, white crystalline powder, mp ˃230ºC (decomp.). IR spectrum, , cm-1: 3421, 3288, 3230 (N–H), 2218,
1
3
2190 (sh) (C≡N), 1718, 1712 (2С=О). Н NMR spectrum, , ppm (J, Hz): 3.87 (2Н, d, J = 7.0, SeCH2); 5.00
(1Н, d, 3J = 9.1, cis-СН=СН2); 5.25 (1Н, d, 3J = 16.7, trans-СН=СН2); 5.93-6.03 (1Н, m, СН=СН2); 7.91 (1Н,
s, Н-4); 17.53 (1Н, br. s, СООH). The NH proton signal is not seen, apparently due to deuterium exchange.
Found, %: C 42.34; H 2.96; N 9.75. C10H8N2О3Se. Calculated, %: C 42.42; H 2.85; N 9.89.
5-Cyano-2-oxo-6-[(2-oxo-2-ethoxyethyl)seleno]-1,2-dihydropyridine-3-carboxylic Acid (12b). Yield
88 mg (57%), yellow, finely crystalline powder, mp 242-244ºC. IR spectrum, , cm-1: 3388, 3185 (N–H), 2218
(C≡N), 1724, 1710 (2С=О). 1Н NMR spectrum, , ppm (J, Hz): 1.23 (3Н, t, 3J = 7.1, ОСН2СН3); 4.01 (2Н, br.
s, SeCH2); 4.11 (2Н, q, 3J = 7.1, ОСН2СН3); 7.95 (1Н, s, Н-4), 17.40 (1Н, br. s, СOОH). The NH proton signal
is not seen, apparently due to deuterium exchange. 13C NMR spectrum, , ppm: 13.9* (CH2CH3);
25.8 (SeCH2); 61.0 (CH2CH3); 108.5 (C-3(5)); 116.2 (С≡N); 117.7 (C-5(3)); 142.3* (C-4); 160.9 (C-2); 167.6
(C=O); 169.6 (C=O); 171.4 (C=O). Found, %: C 39.97; H 3.11; N 8.37. C11H10N2О5Se. Calculated, %: C 40.14;
H 3.06; N 8.51.
_______
* Out of phase signal.
1304

5-Cyano-2-oxo-6-{[2-oxo-2-(phenylamino)ethyl]seleno}-1,2-dihydropyridine-3-carboxylic Acid (12c).
Yield 60 mg (34%), brown, finely crystalline powder, mp 209-211ºC. IR spectrum, , cm-1: 3268 (N–H), 2221
1
3
(C≡N), 1725, 1710 (2С=О). Н NMR spectrum, , ppm (J, Hz): 4.18 (2Н, br. s, SeCH2); 7.01 (1Н, t, J = 7.4,
3
3
3
Н-4 Ph); 7.25 (2Н, dd, J = 7.4, J = 8.3, Н-3,5 Ph); 7.56 (2Н, d, J = 8.3, Н-2,6 Ph); 8.30 (1Н, s, Н-4); 10.23
(1Н, s, NHPh). The endocyclic NH proton signal is not seen, apparently due to deuterium exchange. Found, %:
C 47.71; H 2.99; N 11.01. C15H11N3О4Se. Calculated, %: C 47.89; H 2.95; N 11.17.
2,2'-Diselane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles) 14a,b (General Method).
The cyanoselenoacetamide 10 (1.0 g, 6.8 mmol), diketone 4 or 5 (6.8 mmol), and 96% EtOH (25 ml) were
placed in a flat-bottomed flask of volume 100 ml, and the mixture was stirred under an argon stream for 5 min.
KOH (0.76 g, 13.6 mmol) was added to the suspension. The flask was sealed; the reaction mixture was stirred to
dissolution of the starting reagents and left for 12 h in a fridge at 2-3ºC. 10% HCl was added dropwise with
stirring under an argon stream to the solution formed to pH 3-4 and left for 12 h. The precipitate formed was
filtered off and washed with EtOH.
2,2'-Diselane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile) (14a). Yield 1.46 g
(86%), red-orange, finely crystalline powder, mp 231-233ºC. IR spectrum, , cm-1: 2222 (C≡N), 1710-1650
(2С=О). 1Н NMR spectrum, , ppm: 2.08-2.15 (4Н, m, 7,7'-СН2); 2.53-2.56 (4Н, m, 8,8'-СН2); 3.08-3.11 (4Н, m,
6,6'-СН2); 8.14 (2Н, s, Н-4,4'). 13C NMR spectrum, , ppm: 19.8 (C-7,7'); 26.9 (C-8,8'); 36.6 (C-6,6'); 116.9
(2С≡N); 119.3 (C-3,3'(4а,4а')); 120.2 (C-4а,4а'(3,3')); 139.1* (C-4,4'); 162.2 (C-8a,8a'); 173.4 (C-2,2'); 193.0
(2C=O). Mass spectrum, m/z: 501 [M+Н]+. Found, %: C 47.85; H 2.92; N 11.11. C20H14N4О2Se2. Calculated, %:
C 48.02; H 2.82; N 11.20.
2,2'-Diselane-1,2-diylbis(7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile) (14b). Yield
1.69 g (89%), brick-red, finely crystalline powder, mp 199-201ºC. IR spectrum, , cm-1: 2227 (C≡N), 1680
1
(С=О). Н NMR spectrum, , ppm: 1.11 (12Н, br. s, 4CH3); 2.41 (4Н, br. s, 8,8'-СН2); 2.96 (4Н, br. s,
6,6'-СН2); 8.09 (2Н, s, Н-4,4'). 13C NMR spectrum, , ppm: 27.5* (4CH3); 32.3 (C-8,8'); 49.9 (C-6,6'); 50.7
(C-7,7'); 116.8 (2С≡N); 119.3 (C-3,3'(4а,4а')); 125.2 (C-4а,4а'(3,3')); 138.1* (C-4,4'); 160.3 (C-8a,8a'); 165.9
(C-2,2'); 192.8 (2C=O). Mass spectrum, m/z: 557 [M+Н]+. Found, %: C 51.64; H 4.11; N 9.91. C24H22N4О2Se2.
Calculated, %: C 51.81; H 3.99; N 10.07.
Quinoline 16 and Selenophenoquinolines 17a-d (General Method). A mixture of the diselane 14a,b
(1.00 mmol), 10% KOH (0.6 ml, 1.17 mmol), and 70% EtOH (30 ml) was stirred at room temperature for 5 min,
and the corresponding alkyl halide (1.00 mmol) was added. The mixture was refluxed for 1-2 min with vigorous
stirring, rapidly passed through a paper filter, and left for 48 h at room temperature. The precipitate formed was
filtered off and washed with EtOH and hexane.
Methyl [(3-Cyano-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)seleno]acetate (16). Yield
110 mg (31%), white, finely crystalline powder, mp 94-96ºC. IR spectrum, , cm-1: 2225 (C≡N), 1740, 1691
1
(2С=О). Н NMR spectrum, , ppm: 1.08 (6Н, br. s, 2СН3); 2.52 (2Н, br. s, 8-СН2); 2.95 (2Н, br. s, 6-СН2);
3.67 (2Н, br. s, SeСН2); 4.10 (3Н, s, ОСН3); 8.30 (1Н, s, Н-4). Found, %: C 51.07; H 4.68; N 7.89.
C15H16N2О3Se. Calculated, %: C 51.29; H 4.59; N 7.97.
3-Amino-2-(4-methylbenzoyl)-7,8-dihydroselenopheno[2,3-b]quinolin-5(6H)-one (17a). Yield 92 mg
(24%), yellow, finely crystalline powder, mp 257-259ºC (decomp.). IR spectrum, , cm-1: 3385, 3235 (NH2),
1
1725, 1680 (2С=О). Н NMR spectrum, , ppm (J, Hz): 2.18-2.25 (2Н, m, 7-СН2); 2.44 (3Н, s, ArСН3); 2.68-
2.72 (2Н, m, 8-СН2); 3.16-3.20 (2Н, m, 6-СН2); 7.25 (2Н, d, 3J = 8.1, H Ar); 7.63 (2Н, d, 3J = 8.1, H Ar); 8.61
(2Н, br. s, NH2); 9.11 (1Н, s, Н-4). Found, %: C 59.37; H 4.29; N 7.22. C19H16N2О2Se. Calculated, %: C 59.54;
H 4.21; N 7.31.
_______
* Out of phase signal.
1305

3-Amino-2-benzoyl-7,8-dihydroselenopheno[2,3-b]quinolin-5(6H)-one (17b). Yield 107 mg (29%),
yellow-green, finely crystalline powder, mp 253-255ºC (decomp.). IR spectrum, , cm-1: 3390, 3270 (NH2),
1
1676 (2С=О). Н NMR spectrum, , ppm: 2.18-2.24 (2Н, m, 7-СН2); 2.69-2.72 (2Н, m, 8-СН2); 3.17-3.20
(2Н, m, 6-СН2); 7.44-7.52 (3Н, m, Н Ph); 7.71-7.73 (2Н, m, Н Ph); 8.67 (2Н, br. s, NH2); 9.12 (1Н, s,
Н-4). 13C NMR spectrum, , ppm: 21.0 (C-7); 32.3 (C-8); 38.0 (C-6); 101.0 (С Ar); 125.0 (СAr); 126.6*
(С-3,5 Ph); 128.1 (С Ar); 128.6* (С-2,6 Ph); 131.0*, 132.0* (C-4, C-4 Ph); 141.9 (С-i Ph); 152.8 (С Ar);
165.2 (С Ar); 167.8 (С Ar); 190.1 (C=O); 197.0 (C=O). Found, %: C 58.33; H 3.91; N 7.47. C18H14N2О2Se.
Calculated, %: C 58.55; H 3.82; N 7.59.
3-Amino-7,7-dimethyl-2-(4-methylbenzoyl)-7,8-dihydroselenopheno[2,3-b]quinolin-5(6H)-one (17c).
Yield 177 mg (43%), yellow-green, finely crystalline powder, mp 222-224ºC. IR spectrum, , cm-1: 3388, 3281,
3198 (NH2), 1680 (2С=О). 1Н NMR spectrum, , ppm (J, Hz): 1.12 (6Н, br. s, 2CH3); 2.42 (3Н, s, ArCH3); 2.55
(2Н, br. s, 8-СН2); 3.05 (2Н, br. s, 6-СН2); 7.23 (2Н, d, 3J = 8.4, H Ar); 7.61 (2Н, d, 3J = 8.4, H Ar); 8.60 (2Н,
br. s, NH2); 9.08 (1Н, s, Н-4). Found, %: C 61.11; H 4.98; N 6.67. C21H20N2О2Se. Calculated, %: C 61.32;
H 4.90; N 6.81.
3-Amino-2-benzoyl-7,7-dimethyl-7,8-dihydroselenopheno[2,3-b]quinolin-5(6H)-one (17d). Yield
207 mg (52%), yellow-green, finely crystalline powder, mp 249-251ºC. IR spectrum, , cm-1: 3368, 3264, 3175
1
(NH2), 1677 (2С=О). Н NMR spectrum, , ppm (J, Hz): 1.12 (6Н, br. s, 2CH3); 2.58 (2Н, br. s, 8-СН2); 3.07
(2Н, br. s, 6-СН2); 7.46-7.49 (3Н, m, H Ph); 7.70-7.72 (2Н, m, H Ph); 8.69 (2Н, br. s, NH2); 9.11 (1Н, s, Н-4).
13C NMR spectrum, , ppm: 27.7* (2CH3); 32.5 (C-8); 45.7 (C-6); 51.2 (C-7); 101.1 (С Ar); 124.0 (С Ar);
126.6* (С-3,5 Ph); 128.1 (С Ar); 128.6* (С-2,6 Ph); 131.0*, 131.6* (C-4, C-4 Ph); 141.9 (С-i Ph); 152.8
(С Ar); 163.7 (С Ar); 167.8 (С Ar); 190.0 (C=O); 196.9 (C=O). Found, %: C 60.27; H 4.65; N 6.91.
C20H18N2О2Se. Calculated, %: C 60.46; H 4.57; N 7.05.
_______
* Out of phase signal.
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