On the reactivity of benzo[a]phenazine-5,6-dione 7-oxides with methanolic alkali and pyrrolidine

Article abstract of DOI:10.1007/s10593-015-1676-7

[MediaObject not available: see fulltext.]When treated with methanolic alkali, benzo[a]phenazine-5,6-dione 7-oxides convert into 11H-indeno[1,2-b]quinoxalin-11-ones, whereas 11-hydroxy-11-(pyrrolidine-1-carbonyl)-11H-indeno[1,2-b]quinoxaline 10-oxides form upon treatment with pyrrolidine.

Full text of DOI:10.1007/s10593-015-1676-7

DOI 10.1007/s10593-015-1676-7
Chemistry of Heterocyclic Compounds 2015, 51(2), 166–169
On the reactivity of benzo[a]phenazine-5,6-dione 7-oxides
with methanolic alkali and pyrrolidine
1
2
1
Leonid M. Gornostaev *, Tatyana A. Rukovets , Elena V. Arnold ,
1
1
2
Tatyana I. Lavrikova , Juliya G. Khalyavina , Irina S. Kryukovskaya
1
Krasnoyarsk State Pedagogical University named after V. P. Astaf'ev,
8
9 A. Lebedeva St., Krasnoyarsk 660049, Russia; е-mail: gornostaev@kspu.ru
2
Krasnoyarsk State Medical University named after Professor V.F. Voyno-Yasenetsky,
Partizan Zheleznyak St., Krasnoyarsk 660021, Russia; е-mail: tatyana_xim@mail.ru
1
Translated from Khimiya Geterotsiklicheskikh Soedinenii,
Submitted December 31, 2014
Accepted January 19, 2015
2
015, 51(2), 166–169
2
2
2
R
R
R
N
N
N
N
, THF
KOH, MeOH
20–25°C, 1 h
1
+
1
1
+
20–25°C, 30 min
R
N
R
N
R
N
O
N
HO
O
O
O
O
O
When treated with methanolic alkali, benzo[а]phenazine-5,6-dione 7-oxides convert into 11Н-indeno[1,2-b]quinoxalin-11-ones, whereas
1-hydroxy-11-(pyrrolidine-1-carbonyl)-11Н-indeno[1,2-b]quinoxaline 10-oxides form upon treatment with pyrrolidine.
1
Keywords: benzo[а]phenazine-5,6-dione 7-oxides, 11Н-indeno[1,2-b]quinoxalin-11-ones, benzilic acid rearrangement.
Phenazine N-oxides and dioxides attract the attention of
researchers as substances exhibiting a range of biological
activities. It is known that phenazine N-oxide possesses
We have found that benzo[а]phenazine-5,6-dione
7-oxides 1а–е are converted into 11Н-indeno[1,2-b]-
quinoxalin-11-ones 2а–е when treated with methanolic
potassium hydroxide solution at 20-25°C. The reaction is
1
antibacterial activity , and its hydroxyl and amide
2
,3
derivatives exhibit antitumor activity . Also, phenazine
,10-dioxides were recently identified as prodrugs for
accompanied by the release of CO , contraction of the
2
5
ortho-quinoid ring, and deoxygenation of the N-oxide
fragment (Scheme 1).
The structure of 11Н-indeno[1,2-b]quinoxalin-11-ones
2а-е, currently studied in view of their antimicrobial,
4
,5
antitumor therapy due to cytotoxic properties. Study of
the chemical properties of phenazine N-oxides, therefore, is
of interest.
Scheme 1
2
2
2
R
R
R
N
N
H+
N
KOH, MeOH
1
+
20–25°C, 1 h
1
+
O
– CO2
1
+
R
N
O
R
N
R
N
O
OH
O
O
OH
O
O
1a–e
2
2
R
R
N
N
N
1
– H O
2
R
1
R
N
OH
O
OH
2
a–e
(58–83%)
2
1
1
1
1
2
1
, 2 a–d R = H, a,e R = H, b R = Me, c R = Cl, d R = F, e R = Me
0
009-3122/15/5102-0166©2015 Springer Science+Business Media New York
166

Chemistry of Heterocyclic Compounds 2015, 51(2), 166–169
Scheme 4
antihypertensive, antituberculosis, antimalaria, anti-inflamma-
tory, anticonvulsant, antiHIV, and anticancer activity, was
6-8
O
O
N
O
N
verified by counter synthesis of compound 2а from ninhydrin
HO
9
,10
and 1,2-diaminobenzene (Scheme 2).
OH–
Characteristically, the signals of the quinonoid carbon
N
13
atoms in the C NMR spectra of benzo[а]phenazine-5,6-
dione 7-oxides 1а–е are in the 171-178-ppm range, while the
N
Scheme 2
5
6
O
H N
N
N
phenanthrenequinones and their diaza-analogs is absent in
the literature.
To conclude, we have found unique reactions of benzo[а]-
phenazine-5,6-dione 7-oxides, with their direction explained
by structural features of the starting materials, namely, the
presence of N-oxide moiety in their molecules.
2
OH
OH
+
H N
2
O
O
2
a
13
signal of the single carbonyl carbon atom in C NMR spectra
of 11Н-indeno[1,2-b]quinoxalin-11-ones 2а–е is at ~190 ppm,
11
which correlates with literature data. Our attempts to isolate
any of the intermediates in the reaction 1→2 were
unsuccessful. When phenazine N-oxides 1а–е were treated
with methanolic KOH at low temperature (0–5°C), as well as
treating them with potassium phenoxide in dioxane (at 15–
Scheme 5
2
R
N
N
,
THF
1a,b,e
2
0°C), only the corresponding quinoxalines 2а–е are formed.
1
+
N
2
0–25 °C, 30 min
R
The reaction 1→2 differs from classical cases of benzilic
N
HO
acid rearrangement of ortho-quinonoid polycyclic compounds
73–77%
O
O
1
2
such as phenanthrenequinone 3 reaction with alkalis where
7a,b,c
the main products are derivatives of 9-hydroxyfluorene-
1
2
1
2
1
2
7
a R = R = H; b R = Me, R = H; c R = H, R = Me
9-carboxylic acid 4 (Scheme 3).
Notably, the rearrangement of phenanthrenequinones
Experimental
into 9-hydroxyfluorene-9-carboxylic acids is greatly
facilitated by electron-withdrawing substituents in the
benzenoid fragment of phenanthrenequinone. Thus,
unsubstituted phenanthrenequinone isomerizes to the
corresponding hydroxyfluorenecarboxylic acid under
prolonged heating at 80°C, 2- and 4-mononitro-
Scheme 3
IR spectra were registered on a Shimadzu IRAffinity-1
spectrometer in KBr pellets. UV spectra were recorded on
an Evolution 300 (10-mm cuvettes) spectrophotometer in
1
13
acetonitrile. H and C NMR spectra were acquired on a
Bruker DRX spectrometer (500 and 125MHz, respectively)
in DMSO-d
6 3
(compounds 1e, 2a–e) or СDCl (compounds
7
a–с), with TMS as internal standard. Chemical shifts of
O
O
COOH
HO
13
11
OH–
С nuclei were assigned using published data. Mass
R
R
spectra were recorded on a Finnigan MAT 8200 (EI
ionization, 70 eV) mass spectrometer. High-resolution
mass spectra for compounds 1e and 2e were recorded on a
Thermo Scientific DFS (direct injection, EI ionization,
3
4
R = H, Br, NO2
70 eV), whereas for compounds 7b,c they were acquired on
phenanthrenequinones at 65°C, whereas 2,7- and 4,5-di-
nitrophenanthrenequinones at 15°C.
a
Bruker microOTOF II mass spectrometer with
electrospray ionization in positive-ion mode (voltage
14
Dibenzophenazinedione 5, a closer related analog of
benzo[а]phenazine-5,6-dione 7-oxides, transforms in low
yield into 2-quinoxalylbenzoic acid 6 only when boiled with
applied to capillary 4500 V). Scanned mass range m/z 50–
3000. Direct infusion of acetonitrile solution of samples by
syringe pump was used, flow rate 3 ml/min. Nitrogen
nebulizing gas (4 l/min), interface temperature 180°С.
Elemental analysis was performed on a EURO EA 3000
Elemental Analyzer. Melting points were determined on a
Boetius heating bench. Monitoring of the reaction progress
and assessment of the purity of synthesized compounds
was done by TLC on Silufol UV-254 plates (eluent:
toluene–acetone, 10:1).
1
3
concentrated aqueous NaOH (Scheme 4).
Therefore, the presence of an N-oxide fragment in
phenazinedione derivatives 1а–е enhances their reactivity
towards and selectivity in the electrophilic reaction with
alkalis. Increased electrophilic reactivity of phenazinedione
N-oxides is also confirmed by the reaction of compounds
1а,b,е with pyrrolidine, resulting in 11-hydroxy-
11-(pyrrolidin-1-ylcarbonyl)-11Н-indeno[1,2-b]quinoxaline
10-oxides 7а–с with preservation of the N-oxide moiety
The starting benzo[а]phenazine-5,6-dione 7-oxides 1а–d
15
were prepared according to published procedures, while
oxide 1е was prepared analogously. 4-(о-Tolylamino)-1,2-
naphthoquinone was synthesized following a published
(
7
Scheme 5). The structure and composition of compounds
а–с were confirmed by physicochemical analysis. It
should be noted that data on amine-induced cleavage of
16
method.
1
67

Chemistry of Heterocyclic Compounds 2015, 51(2), 166–169
1
1-Methyl-5,6-dioxobenzo[а]phenazine 7-oxide (1е).
Nitrosylsulfuric acid, prepared from sodium nitrite (2.50 g,
5 mmol) and concentrated sulfuric acid (15 ml) was added
(58%), yellow crystals, mp 282°С (benzene). IR spectrum,
–1
ν, cm : 1730 (С=О). UV spectrum, λmax, nm (log ε): 291 (4.52).
1
3
H NMR spectrum, δ, ppm (J, Hz): 7.74 (1Н, t, J = 7.5, H-3);
over 5 min to a solution of 4-(о-tolylamino)-1,2-naphtho-
quinone (2.63 g, 10 mmol) in glacial acetic acid (60 ml). The
reaction mixture was stirred for 1 h at 15–20°С, then poured
with stirring into ice/water mixture (200 ml). The formed
precipitate was filtered off, washed with water until neutral
reaction, and dried. Yield 2.60 g (90%), red crystals, mp 248°С
7.89 (1Н, d, J = 7.5, H-4); 7.91 (1Н, t, J = 7.5,
H-2); 7.95 (1Н, dd, J = 7.4, J = 2.4, H-7); 8.1 (1Н, d, J = 7.4,
H-6); 8.16 (1Н, d, J = 7.5, H-1); 8.28 (1Н, d, J = 2.4, H-9).
13
C NMR spectrum, δ, ppm: 122.6 (С-4); 124.9 (С-2); 130.4
(С-3); 130.7 (С-7); 132.8 (С-6); 133.2 (С-9); 136.1 (С-8); 136.7
(С-1); 137.0 (С-11а); 141.4 (С-4а); 141.7 (С-5а); 143.0 (С-4b);
150.8 (С-9а); 156.7 (С-10а); 189.6 (С-11). Mass spectrum, m/z
–1
(
DMF). IR spectrum, ν, cm : 1356 (N–O), 1672 (C=O).
1
37
+
35
+
H NMR spectrum, δ, ppm (J, Hz): 2.85 (3Н, s, СН
.63 (2Н, m, Н-3,9); 7.90 (1Н, d, J = 7.2, Н-10); 7.96 (1Н,
t, J = 7.8, Н-2); 8.11 (1Н, d, J = 7.8, Н-1); 8.31 (1Н, d, J = 8.6,
3
); 7.50–
(Irel,%): 268 [M( Cl)] (35), 266 [M( Cl)] (100), 75 (45), 50
(35), 32 (24). Found, %: С 67.41; Н 2.54; N 10.49; Сl 13.30.
7
C
15
H
7
СlN
2
O. Calculated, %: С 67.56; Н 2.65; N 10.50;
13
Н-4); 8.85 (1Н, d, J = 7.9, Н-8). C NMR spectrum, δ, ppm:
7.3 (СН ); 117.4 (С-10); 126.7 (С-8); 128.4 (С-3); 131.1
С-2); 132.2 (С-9); 132.3 (С-11а); 133.6 (С-12b); 135.0 (С-4а);
35.6 (С-1); 138.3 (С-7а); 139.1 (С-11); 142.5 (С-12а); 149.4
Сl 13.29.
1
(
1
3
8-Fluoro-11Н-indeno[1,2-b]quinoxalin-11-one (2d)
was prepared analogously to compound 2а. Yield 0.59 g
(81%), yellow crystals, mp 298°С (benzene). IR
+
–1
(С-6а); 171.5 (С-5); 177.7 (С-6). Found, m/z: 290.0684 [M] .
spectrum, ν, cm : 1724 (С=О). UV spectrum, λmax, nm
1
С
17
Н
10
N
2
O
3
. Calculated, m/z: 290.0686. Found, %: С 69.86;
(log ε): 288 (4.52). H NMR spectrum, δ, ppm (J, Hz):
Н 3.28; N 9.66. С17
Н
10
N
2
O
3
. Calculated, %: С 70.34; Н 3.47;
7.69–7.73 (2H, m, H-2,3); 7.81–7.86 (1H, m, H-7); 7.88
N 9.65.
(1Н, d, J = 7.5, H-4); 7.96 (1Н, d, J = 10.0, H-6); 8.06
1
3
11Н-Indeno[1,2-b]quinoxalin-11-one (2а). Benzo[а]-
(1Н, d, J = 7.5, H-1); 8.17–8.22 (1H, m, H-9). C NMR
spectrum, δ, ppm: 115.3 (С-7); 115.5 (С-9); 122.5 (С-4);
124.9 (С-2); 131.5 (С-3); 132.6 (С-6); 136.5 (С-1); 137.0
(С-11а); 140.3 (С-4а); 141.5 (С-5а); 143.6 (С-4b); 150.0
(С-9а); 156.2 (С-10а); 163.2 (С-8); 189.6 (С-11). Mass
phenazine-5,6-dione 7-oxide (1а) (0.8 g, 2.9 mmol) was
added to a solution of KOH (1.0 g, 0.018 mol) in MeOH
(
2
15 ml), and the resulting mixture heated for 60 min at 20–
5°С Then 5% aqueous hydrochloric acid was added to the
.
+
mixture. The precipitate was filtered off, washed with
water followed by ethanol. Yield 0.56 g (83%), yellow
crystals, mp 227°С (toluene) (mp 195–200°С , mp 222°С ).
spectrum, m/z (Irel,%): 250 [M] (100), 222 (24), 94 (18), 75
(20), 50 (20). Found, %: С 72.27; Н 2.80; N 11.47.
6
7
C
15
H
7
FN
2
O. Calculated, %: С 72.00; Н 2.82; N 11.19.
–
1
IR spectrum, ν, cm : 1730 (С=О). UV spectrum, λmax, nm
6-Methyl-11Н-indeno[1,2-b]quinoxalin-11-one (2е)
1
(
(
log ε): 286 (4.54). H NMR spectrum, δ, ppm (J, Hz): 7.71
1Н, t, J = 7.2, H-3); 7.83–7.90 (2H, m, H-7,8); 7.88 (1Н,
was synthesized similar to compound 2а. Yield 0.59 g
(83%), yellow crystals, mp 210°С (toluene). IR spectrum, ν,
–1
d, J = 7.2, H-4), 7.92 (1Н, t, J = 7.2, H-2); 8.08–8.13 (2Н,
m, H-6,9); 8.17 (1Н, d, J = 7.2 , H-1). C NMR spectrum, δ,
ppm: 122.8 (С-4); 124.7 (С-2); 129.8 (С-7); 130.9 (С-8);
cm : 1716 (С=О). UV spectrum, λmax, nm (log ε): 299 (4.55).
13
1
3
H NMR spectrum, δ, ppm (J, Hz): 2.78 (3Н, s, 6-СН );
7.65 (1Н, t, J = 7.5, Н-3); 7.68 (1Н, t, J = 7.5, Н-1); 7.77
(1Н, d, J = 7.2, Н-7); 7.86 (1Н, t, J = 7.2, Н-8); 7.88 (1Н,
d, J = 7.5, Н-4); 7.99 (1Н, d, J = 8.0, Н-9); 8.07 (1Н, d,
1
1
1
31.4 (С-3); 132.9 (С-6); 133.3 (С-9); 137.1 (С-11а);
37.4 (С-1); 141.5 (С-4а); 142.3 (С-5а); 142.6 (С-4b);
50.3 (С-9а); 156.9 (С-10а); 189.8 (С-11). Mass spectrum,
13
3
J = 7.5, Н-1). C NMR spectrum, δ, ppm: 17.2 (СН );
+
m/z (Irel,%): 232 [M] (100), 204 (59), 76 (51), 32 (48).
Found, %: С 77.61; Н 3.42; N 11.84. C15
Calculated, %: С 77.58; Н 3.47; N 12.06.
122.4 (С-4); 124.5 (С-2); 129.1 (С-7); 130.2 (С-8,9); 130.3
(С-8,9); 132.9 (С-3); 136.8 (С-6); 137.2 (С-1); 137.7 (С 4);
141.9 (С-4а); 141.4 (С-4b); 142.2 (С-5а); 149.6 (С-9а);
8 2
H N O.
+
8
-Methyl-11Н-indeno[1,2-b]quinoxalin-11-one (2b)
was synthesized analogously to compound 2а. Yield 0.55 g
77%), yellow crystals, mp 230°С (benzene). IR spectrum,
155.7 (С-10а); 189.8 (С-11). Found, m/z: 246.0789 [M] .
16 10 2
С Н N O. Calculated, m/z: 246.0788. Found, %: С 78.16;
(
Н 3.90; N 11.35. C16
Н 4.09; N 11.38.
10 2
H N O. Calculated, %: С 78.04;
–1
ν, cm : 1720 (С=О). UV spectrum, λmax, nm (log ε): 295
1
(
8
4.55). H NMR spectrum, δ, ppm (J, Hz): 2.56 (3Н, s,
-СН ); 7.68 (1Н, t, J = 7.8, H-3); 7.74 (1Н, d, J = 8.5,
H-7); 7.85 (1Н, t, = 7.8, H-2); 7.86 (1Н, d, = 7.8, H-4);
.94 (1Н, s, H-9); 8.01 (1Н, d, = 8.5, H-6); 8.04 (1Н, d,
= 7.8, H-1). C NMR spectrum, δ, ppm: 21.6 (СН ); 122.6
11-Hydroxy-11-(pyrrolidin-1-ylcarbonyl)-11
Н-indeno-
3
[1,2-b]quinoxaline 10-oxide (7а). Pyrrolidine (0.2 g,
J
J
2.8 mmol) was added with stirring over 10 min at 20–25°С
to a solution of compound 1a (0.56 g, 2.0 mmol) in
tetrahydrofuran (10 ml). After 30 min, the formed
precipitate was filtered off, washed on filter with water
(50 ml), followed by ethanol (20 ml). Yield 0.53 g (76%),
yellow crystals, mp 275°С (compounds 7a–c begin to change
visually at ~100°С). UV spectrum, λmax, nm (log ε): 322
7
J
J
13
3
(
1
(
(
С-4); 124.7 (С-2); 129.4 (С-7); 130.4 (С-3); 133.0 (С-6);
34.9 (С-9); 136.9 (С-1); 137.4 (С-11а); 141.0 (С-8); 141.2
С-4а); 141.6 (С-5а); 142.4 (С-4b), 150.1 (С-9а); 156.3
С-10а); 190.0 (С-11). Mass spectrum, m/z (Irel,%): 246
+
1
[M] (100), 218 (39), 89 (36), 32 (71). Found, %: С 77.61;
(4.47). H NMR spectrum, δ, ppm (J, Hz): 1.63–1.73 (4Н,
Н 4.03; N 11.12. C16
Н 4.09; N 11.38.
10 2
H N O. Calculated, %: С 78.04;
m, 3,4-СН
(2Н, m, CН
2
pyrrolidine); 2.75–2.82 (2Н, m) and 2.82–2.91
NCH ); 7.68 (1Н, t, J = 7.4, Н-3); 7.82–7.89
2
2
8
-Chloro-11Н-indeno[1,2-b]quinoxalin-11-one
(2c)
(2Н, m, Н-7,8); 7.93 (1Н, t, J = 7.4, Н-2); 8.10 (1Н, d,
J = 7.4, Н-1); 8.23 (1Н, d, J = 8.4, Н-6); 8.64 (1Н, d, J = 8.4,
was synthesized analogously to compound 2а. Yield 0.45 g
1
68

Chemistry of Heterocyclic Compounds 2015, 51(2), 166–169
Н-9); 8.73 (1Н, d, J = 7.8, Н-4); 8.83 (1Н, s, ОН). Found,
: С 69.32; Н 4.76; N 11.98. C20 . Calculated, %:
С 69.15; Н 4.93; N 12.10.
1-Hydroxy-8-methyl-11-(pyrrolidin-1-ylcarbonyl)-
1Н-indeno[1,2-b]quinoxaline 10-oxide (7b) was prepared
from compound 1b (0.59 g, 2.0 mmol) and pyrrolidine
Siberian Branch of the Russian Academy of Sciences) for
performing high-resolution mass spectral analysis.
%
H
17
N
3
O
3
References
1
1
. Tsuda, T.; Fujishima, K.; Ueda, H. Agric. Biol. Chem. 1981,
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4
2
3
. Rewcastle, G. W.; Denny, W. A.; Baguley, B. G. J. Med.
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(
(
(
1
2
0.37 g, 5.2 mmol) similar to compound 7а. Yield 0.53 g
73%), yellow crystals, mp 245°С. UV spectrum, λmax, nm
1
log ε): 326 (4.42). H NMR spectrum, δ, ppm (
J
, Hz):
pyrrolidine); 2.66 (3Н, s, CН );
.75–2.83 (2Н, m) and 2.84–2.89 (2Н, m, CН NCH ); 7.68
.63–1.73 (4Н, m, 3,4-СН
2
3
2
2
4. Gonda, M.; Nieves, M.; Nunes, E.; Cerain, A.; Monge, A.;
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(
1Н, t, J = 7.6, Н-3); 7.73 (1Н, d, J = 7.3, Н-7); 7.83 (1Н, t,
J = 7.4, Н-2); 8.08–8.13 (2Н, m, Н-1,6); 8.42 (1Н, s, Н-9);
.69 (1Н, d, J = 7.6, Н-4); 8.93 (1Н, s, ОН). Found, m/z:
5
. Lavaggi, M.; Cabrera, M.; Anavena, M.; Olea-Azar, C.;
Cerain, A.; Antonio, M.; Pachon, G.; Cascante, M.; Bruno, A.;
Pietrasanta, L.; Gonzalez, M.; Ceretto, H. Bioorg Med. Chem.
8
+
3
62.1496 [M+Н] . C21
Found, %: С 69.82; Н 5.09; N 11.30. C21
: С 69.79; Н 5.30; N 11.63.
1-Hydroxy-6-methyl-11-(pyrrolidin-1-ylcarbonyl)-
1Н-indeno[1,2-b]quinoxaline 10-oxide (7с) was
H
20
N
3
O
3
. Calculated, m/z: 362.1499.
19 3 3
H N O . Calculated,
2
010, 18, 4433.
%
6. Khan, M.; Munawar, M.; Ashraf, M.; Alam, U.; Ata, A.;
1
Asiri, A.; Kousar, S.; Khan, M. Bioorg. Med. Chem. 2014, 22,
1
1195.
synthesized from compound 1e (0.59 g, 2.0 mmol) and
pyrrolidine (0.37 g, 5.2 mmol) analogously to compound
7. Pearson, B. D.; Mitch, R. A.; Cromwell, N. H. J. Org. Chem.
1962, 27, 1674.
7
а. Yield 0.56 g (77%), yellow crystals, mp 250°С. UV
8. Prostakov, N. S.; Pleshakov, V. G.; Zain-ul-Abedin, M.;
Kordova, I. R.; Zakharov, V. F.; Zvolinskii, V. P. Zh. Org.
Khim. 1982, 3, 640.
1
spectrum, λmax, nm (log ε): 327 (4.46). H NMR spectrum,
δ, ppm (J, Hz): 1.63–1.73 (4Н, m, 3,4-СН pyrrolidine);
NCH ); 2.84–
); 7.65–7.77 (3Н, m, Н-3,7,8); 7.83
2
9
1
1
. Zain-ul-Abedin, M.; Pleshakov, V. G.; Sergeeva, N. D.;
Prostakov, N. S. J. Bangladesh Acad. Sci. 1996, 20, 17.
0. Daddy, L.; Desneves, J.; Ross, A. Tetrahedron 1993, 49,
2
2
.86 (3Н, s, CН
.89 (2Н, m, CН
3
); 2.75–2.83 (2Н, m, CН
NCH
2
2
2
2
(
1Н, t, J = 7.5, Н-2); 8.10 (1Н, d, J = 7.5, Н-1); 8.47 (1Н, d,
9
823.
J = 8.3, Н-9); 8.75 (1Н, d, J = 7.7, Н-4); 8.91 (1Н, s, ОН).
1. Pretsch, E.; Bühlmann, P.; Affolter, C. Structure
Determination of Organic Compounds. Tables of Spectral
Data [in Russian]; Mir: Moscow, 2006, p. 116.
+
Found, m/z: 362.1496 [M+Н] . C21
m/z: 362.1499. Found, %: С 69.53; Н 5.01; N 11.69.
. Calculated, %: С 69.79; Н 5.30; N 11.63.
20 3 3
H N O . Calculated,
C
21
H
19
N
3
O
3
12. Schmidt, J.; Bauer, K. Chem. Ber. 1905, 38, 3737.
1
1
3. Fischer, O.; Schindler, E. Chem. Ber. 1908, 41, 392.
4. Belyakov, P. A., Kadentsev, V. I., Chizhov, A. O.,
Kolotyrkina, N. G., Shashkov, A. S., Ananikov, V. P.
Mendeleev Commun. 2010, 20, 125.
This work was financially supported by a grant of the
Ministry of Education and Science of the Russian Federation
2014-2016 - project № 2854).
(
1
5. Gornostaev, L. M.; Arnold, E. V.; Lyashchenko, T. A. Chem.
Heterocycl. Compd. 2014, 49, 1827. [Khim. Geterotsikl.
Soedin. 2013, 1972.]
The authors are indebted to O. A. Chizhov (N. D. Zelinsky
Institute of Organic Chemistry, Russian Academy of
Sciences), A. A. Nefedov, and O. B. Statsenko (N. N.
Vorozhtsov Novosibirsk Institute of Organic Chemistry,
16. Harmon, R. E., Phipps, L. M., Howell, J. A., Gupta, S. K.
Tetrahedron. 1969, 25, 5807.
1
69