Schiff bases derived from 6-amino-2H-chromen-2-one. Synthesis and 1H NMR spectra

Article abstract of DOI:10.1007/s11178-005-0294-8

A number of 6-arylmethylideneamino-2H-chromen-2-ones were synthesized by reaction of 6-amino-2H-chromen-2-one with aromatic and heterocyclic aldehydes. A linear relation was revealed between the chemical shifts of the azomethine CH=N proton and protons in

Full text of DOI:10.1007/s11178-005-0294-8

Russian Journal of Organic Chemistry, Vol. 41, No. 7, 2005, pp. 1064–1070. Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005,
pp. 1085–1091.
Original Russian Text Copyright © 2005 by Ganushchak, Kobrin, Bilaya, Mizyuk.
Schiff Bases Derived from 6-Amino-2H-chromen-2-one.
1
Synthesis and H NMR Spectra
1
1
1
2
N. I. Ganushchak , L. O. Kobrin , E. E. Bilaya , and V. L. Mizyuk
1
Ivan Franko L’viv National University, ul. Kirilla i Mefodiya 6, L’viv, 79005 Ukraine
e-mail: lkobryn2002@mail.ru
2
Ukrainian Academy of Printing, L’viv, Ukraine
Received August 2, 2004
Abstract—A number of 6-arylmethylideneamino-2H-chromen-2-ones were synthesized by reaction of
6
-amino-2H-chromen-2-one with aromatic and heterocyclic aldehydes. A linear relation was revealed between
the chemical shifts of the azomethine CH=N proton and protons in the chromene ring, on the one hand, and
Hammett constants σ of the para substituents, on the other. Formation of intramolecular hydrogen bond in
ortho-hydroxy derivatives induces a downfield shift of signals from protons in positions 3–5, 7, and 8 and
CH=N proton (9-H) and upfield shift of the o-H signal (14-H).
Compounds of the coumarin series are fluorescent
dyes and materials for dye lasers [1–4]. These com-
pounds include N-arylmethylidene derivatives (Schiff
bases) of 6-amino-2H-chromen-2-one, which were re-
ported by us previously [5]. In order to study in detail
their spectral parameters with regard to the nature of
substituent in the arylmethylidene fragment, we have
synthesized a number of new Schiff bases belonging
to this series.
substituted benzaldehydes, and Schiff bases XXXIIІ–
XXXVIII, from polycyclic and heterocyclic alde-
hydes. The products were isolated and purified by
standard procedures. They were yellow to orange
crystalline substances. The structure of compounds І–
1
XXXVIII was confirmed by the H NMR spectra (see
Experimental), and physical constants of previously
described compounds ІI, III, X, and XV coincided
1
with published data [5–7]. The H NMR spectra of the
Compounds І–XXXVIII were obtained by conden-
newly synthesized compounds were recorded from
sation of the corresponding aldehydes with 6-amino-
0.08 M solutions in DMSO-d at 25°C. It seemed to be
6
2
H-chromen-2-one in anhydrous alcohol or dioxane in
reasonable to compare their spectral parameters (i.e.,
chemical shifts and coupling constants) and correlate
these parameters with their structure, specifically with
the presence of a catalytic amount of piperidine on
heating for 6 h under reflux. 6-Arylmethylideneamino-
2
1
5
H-chromen-2-ones І–XXXII were synthesized from
the nature of R –R substituents in the phenyl ring.
R4
R3
13
R5
1
2
14
5
8
4
5
8
4
N
X
N
6
6
R2
11
3
3
1
0
9
9
R1
7
7
O
O
O
O
I–XXXII
XXXIII–XXXVII
3
3
3
3
3
3
3
3
I, R = Et
2
N; II, R = Me
2
N; III, R = HO; IV, R = EtO; V, R = MeS; VI, R = Et; VII, R = AcNH; VIII, R = 5-carboxy-1-
3
3
3
3
3
3
1
1
2
methylpyrazol-3-yl; IX, R = BzO; X, R = H; XI, R = Cl; XII, R = Br; XIII, R = CN; XIV, R = O N; XV, R = HO; XVI, R =
1
1
1
1
3
2
3
4
2
3
2
EtO; XVII, R = F; XVIII, R = Cl; XIX, R = O N; XX, R = R = Me; XXI, R = R = R = MeO; XXII, R = MeO, R = HO;
3 2 3 1 4
2
3
2
XXIII, R = MeO, R = PrO; XXIV, R = MeO, R = BzO; XXV, R = MeO, R = p-FBzO; XXVI, R = MeO, R = Br; XXVII,
1
2
4
2
2
3
1
4
1
5
R = HO, R = R = Cl; XXVIII, R = O
2
N; XXIX, R = O
R = MeO, R = 5-carboxy-1-methylpyrazol-3-yl; XXXIII, X = 2-hydroxy-1-naphthyl; XXXIV, X = 9-anthryl; XXXV, X =
-pyridyl; XXXVI, X = 2-hydroxy-6-methylquinolin-3-yl; XXXVII, X = 2-methylindol-3-yl; XXXVIII, X = 1,2-dimethylindol-
2 2
N, R = Cl; XXX, R = Cl, R = O N; XXXI, R = F, R = Cl; XXXII,
2
3
3
i
3
-yl; R = H unless otherwise stated.
1
070-4280/05/4107-1064 © 2005 Pleiades Publishing, Inc.

SCHIFF BASES DERIVED FROM 6-AMINO-2H-CHROMEN-2-ONE.
1065
i
Δδ , ppm
In our belief, the most interesting series are para-
substituted compounds І–XIV (R ≠ H) and ortho-sub-
3
0.2
stituted 6-arylmethylideneamino-2H-chromen-2-ones
1
XV–XIX (R ≠ H). For these compounds we examined
the effect of the corresponding substituent (R or R )
0
0
.1
.0
3
1
Br
Cl
on the chemical shifts δ of protons in the coumarin
і
fragment (і = 3–5, 7, 8) and proton at the azomethine
bond (9-H, i = 9). We previously showed [8] that the
effect of a substituent on the chemical shifts of remote
protons may be appreciable even at a distance of
CN NO
2
–
1
–
–
–
0.1
0.2
0.3
– 2
Et
EtO
–
3
H
AcNH
MeS
– 4
– 5
– 6
1
5 interatomic bonds. Our data indicate that the chem-
HO
ical shifts δ of each of the six examined protons (і =
і
3
–5, 7–9) correlate with electronic properties of the
3
R substituent. For the sake of convenience, we shall
Me
2
N
consider the difference ∆δ between the chemical shifts
і
–
0.8
–0.4
0.0
0.4
0.8
σ
p
3
of the іth proton in compounds with R ≠ H and the
3
same proton in benzaldehyde derivative X (R = H). It
Correlations between the differences in the chemical shifts
Δδ of substituted and unsubstituted Schiff bases and Ham-
mett constants σ for 6-arylmethylideneamino-2H-chromen-
-ones ІI–VII and X–XIV: (1) Δδ , (2) Δδ , (3) Δδ , (4) Δδ
(5) Δδ , (6) Δδ .
і
3
i
is seen that the shorter the distance between H and R ,
the stronger the effect of the latter on ∆δ . As expected,
p
і
2
3
4
5
7
,
the largest ∆δ values are observed for the nearest 9-H
і
8
9
proton, and the smallest (lower by an order of magni-
tude), for the most distant 3-H proton. The ∆δ values
for 4-H, 5-H, 7-H, and 8-H occupy an intermediate
і
latter (in our case, on δ ). Here, the larger the distance
i
from the reaction center (in our case, i-H) to R, the
more similar the above effects [10]. In fact, as follows
from the data for compounds IV and XVI (R = EtO),
place between ∆δ and ∆δ .
3
9
We anticipated the existence of a correlation be-
tween ∆δ and Hammett substituent constants σ . These
XI and XVIII (R = Cl), and XIV and XIX (R = NO
∆δ and Δδ are approximately equal for the most dis-
),
і
p
2
correlations are shown in figure (σ values were taken
o
p
p
from [9]). It is seen that ∆δ is linearly related to σ for
tant protons, 8-H and especially 3-H: the difference
does not exceed 0.025 ppm. The difference ∆δo,p for
4-H, 5-H, and 7-H is larger; it ranges from 0.03 to
0.06 ppm. The ∆δo,p values for 5-H and 7-H (which are
located most closely to R or R ), are negative for
IV/XVI and XIV/XIX and maximal in absolute value,
while the corresponding values for more distant 3-H,
і
p
each іth proton in the series of para-substituted com-
pounds ІI–VII and X–XIV; the correlation coefficients
R for 5-H, 7-H, 8-H, and 9-H are equal to 0.97, and for
1
3
3
-H and 4-H, to 0.93 and 0.89, respectively. We can
conclude that the chemical shifts δ of 3-H–5-H and 7-
і
H–9-H are linear in the donor–acceptor power of the
3
para-substituent (R ), which is characterized by the
4-H, and 8-H protons are positive and minimal. The
9
o,p
Hammett constant σ . The slope (b) of the straight
difference ∆δ is greater by an order of magnitude
p
lines in figure can be regarded as the parameter ρ in
(0.09 to 0.37 ppm) and is positive. These data suggest
a direct effect of the ortho substituent on the nearby
9-H proton.
the Hammett equation. It reflects the sensitivity of
3
each particular proton to the effect of the R substit-
uent. The coefficient b in the linear regression y = a +
A specific series consists of ortho-hydroxy Schiff
bx (y = ∆δ , x = σ , a and b are coefficients) is minimal
1
і
p
bases XV, XXVII, and XXXIII. In the H NMR
for the most distant protons, 3-H and 4-H (b = 0.035),
while the correlation for 9-H is characterized by the
maximal value of b (0.289). The values of b for 5-H,
spectra of these compounds, the 5-H and 7-H signals
are displaced upfield to a considerable extent (δ 7.7–
7
.8 ppm). On the other hand, the 14-H signal in the
7
-H, and 8-H are 0.142, 0.122, and 0.061, respectively.
spectra of XV and XXVII appears strongly upfield, as
compared to all other ortho- and polysubstituted
We compared the δ values for ortho-substituted
і
1
Schiff bases XV–XIX with those found for their ana-
logs having the same substituent in the para position
compounds where R ≠ OH. The 9-H signal of ortho-
hydroxy derivatives XV and XXVII is displaced
1
3
(
R = R ). It is known that most substituents located
downfield relative to the corresponding signals of the
o
p
1
3
1
in the ortho and para positions (R and R ) with
other ortho-substituted compounds where R ≠ OH.
o
p
respect to a reaction center exert similar effects on the
Signals from the more distant 3-H, 4-H, and 8-H
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 7 2005

1
066
GANUSHCHAK et al.
protons in ortho-hydroxy compounds XV, XXVII, and
XXXIII are also displaced downfield relative to the
signals from analogous protons in para-hydroxy deriv-
ative ІII, and the difference ∆δo'–p' is 0.03–0.05 ppm.
Thus for the pair of hydroxy derivatives ІII and XV all
and left to stand for 12 h, and the precipitate was
filtered off. An additional amount of the product can be
isolated by evaporation of the mother liquor. The prod-
ucts were purified by recrystallization from ethanol
(compounds І–VI), ethanol–DMF (1:1) (XІ, XII,
XVII, XIX, XXII), or DMF (VII–X, XIII–XV, XX,
XXI, XXIII–XXXVIII) or by reprecipitation from
ethanol with hexane (XVI, XVIII).
∆
δo–p values are greater than those for the pairs with
1
3
other substituents R and R (EtO, Cl, NO ). A possible
2
reason is formation of intramolecular hydrogen bond
O–H···H which induces, on the one hand, downfield
shift of the 3-H–5-H and 7-H–9-H signals (as well as
of the OH signal to δ 12.8–15.5 ppm) and, on the
other, upfield shift of the ortho-proton signal (14-H).
Presumably, just the formation of H-chelate ring is
responsible for the above displacement of the 3-H–9-H
signals in the spectra of ortho-hydroxy-substituted
6
-(4-Diethylaminobenzylideneamino)-2H-chro-
men-2-one (I). Yield 2.43 g (76%), mp 162–163°C.
1
H NMR spectrum, δ, ppm (J, Hz): 6.413 d (1H, 3-H,
3
3
J = 9.5), 7.979 d (1H, 4-H, J = 9.6), 7.439 d (1H,
4
3
4
5
7
-H, J = 2.0), 7.404 d.d (1H, 7-H, J = 8.9, J = 2.0),
3
.320 d (1H, 8-H, J = 8.7), 8.357 s (1H, 9-H), 7.683 d
(
(
2H, 10-H, 14-H), 6.900 d (2H, 11-H, 13-H), 3.443 q
4H, 2CH ), 1.174 t (6H, 2CH ). Found, %: C 74.83;
1
Schiff bases XV, XXVII, XXXIII. The H NMR spec-
2
3
tra of Schiff bases XXXIII–XXXVIII derived from
polycyclic and heterocyclic aldehydes are character-
H 6.13; N 8.54. C H N O . Calculated, %: C 74.98;
2
0
20
2
2
H 6.29; N 8.74.
ized by upfield (XXXVII, XXXVIІІ; δ 6.40–6.41,
3
6-(4-Dimethylaminobenzylideneamino)-2H-chro-
δ4 7.97–7.98 ppm) or downfield shift of the 3-H and
men-2-one (II). Yield 2.19 g (75%), mp 198–199°C.
4
-H signals (XXXIV; δ 6.49, δ 8.09 ppm).
3 4
1
H NMR spectrum, δ, ppm (J, Hz): 6.416 d (1H, 3-H,
As concerns proton–proton coupling constants in
compounds І–XXXVIII, a fairly strong interaction
3
3
J = 9.5), 7.979 d (1H, 4-H, J = 9.5), 7.449 d (1H,
4
3
4
5
7
-H, J = 1.8), 7.414 d.d (1H, 7-H, J = 8.7, J = 1.8),
between 5-H and 7-H in the coumarin fragment should
3
.326 d (1H, 8-H, J = 8.6), 8.388 s (1H, 9-H), 7.718 d
4
be noted for all the examined compounds. The J5,7
(
(
2H, 10-H, 14-H), 6.736 d (2H, 11-H, 13-H), 3.061 s
6H, 2CH3).
values range from 1.1 Hz for compound VI to 2.5 Hz
for V and XXVII; this parameter was used as a crite-
rion for assignment of the corresponding signals in the
6
-(4-Hydroxybenzylideneamino)-2H-chromen-
1
2-one (III). Yield 1.70 g (64%), mp 243–244°C.
H NMR spectra of І–XXXVIII. The coupling con-
1
3
H NMR spectrum, δ, ppm (J, Hz): 6.426 d (1H, 3-H,
stants between 3-H and 4-H ( J = 9.4, 9.9 Hz) are
generally larger than those between 7-H and 8-H ( J =
3
3
3
J = 9.7), 7.996 d (1H, 4-H, J = 9.5), 7.483 d (1H,
4
3
4
5
-H, J = 2.0), 7.434 d.d (1H, 7-H, J = 8.7, J = 2.1),
8
.5, 9.0 Hz). An exception is the coupling constant
3
3
7.344 d (1H, 8-H, J = 8.6), 8.453 s (1H, 9-H), 7.740 d
J7,8 = 7.9 Hz for compound XIII.
(
(
2H, 10-H, 14-H), 6.852 d (2H, 11-H, 13-H), 9.933 s
1H, OH).
EXPERIMENTAL
6
-(4-Ethoxybenzylideneamino)-2H-chromen-2-
1
The H NMR spectra were recorded on a Bruker
one (IV). Yield 1.96 g (67%), mp 195–196°C.
H NMR spectrum, δ, ppm (J, Hz): 6.432 d (1H, 3-H,
J = 9.8), 8.000 d (1H, 4-H, J = 9.6), 7.505 d (1H,
5-H, J = 2.3), 7.456 d.d (1H, 7-H, J = 8.6, J = 2.4),
7.358 d (1H, 8-H, J = 8.7), 8.517 s (1H, 9-H), 7.852 d
(2H, 10-H, 14-H), 6.988 d (2H, 11-H, 13-H), 4.121 q
(2H, CH ), 1.428 t (3H, CH ). Found, %: C 73.59;
1
spectrometer operating at 400 MHz in a pulse mode;
tetramethylsilane was used as internal reference, and
DMSO-d , as solvent. The coupling constants were
measured with an accuracy of ±0.1 Hz (the data are
given only for the coumarin fragment). The progress of
reactions and the purity of products were monitored by
TLC on Silufol UV-254 plates using benzene–acetone
3
3
4
3
4
6
3
2
3
H 4.93; N 4.52. C H NO . Calculated, %: C 73.71;
1
8
15
3
(
10:1) as eluent; spots were visualized under UV light.
H 5.15; N 4.78.
6
-Arylmethylideneamino-2H-chromen-2-ones І–
6-(4-Methylsulfanylbenzylideneamino)-2H-chro-
men-2-one (V). Yield 2.15 g (73%), mp 156–157°C.
XXXVIII (general procedure). A mixture of 10 mmol
of 6-amino-2H-chromen-2-one, 10 mmol of the corre-
sponding aldehyde, and a few drops of piperidine in
0 ml of anhydrous ethanol was heated for 6 h under
reflux. The mixture was cooled to room temperature
1
H NMR spectrum, δ, ppm (J, Hz): 6.428 d (1H, 3-H,
3
3
J = 9.7), 7.994 d (1H, 4-H, J = 9.7), 7.536 d (1H,
4
3
4
5
5-H, J = 2.5), 7.482 d.d (1H, 7-H, J = 8.8, J = 2.5),
3
7.362 d (1H, 8-H, J = 8.8), 8.563 s (1H, 9-H), 7.846 d
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 7 2005

SCHIFF BASES DERIVED FROM 6-AMINO-2H-CHROMEN-2-ONE.
1067
(
(
2H, 10-H, 14-H), 7.316 d (2H, 11-H, 13-H), 2.547 s
7.952 d (2H, 10-H, 14-H), 7.520 m (4H, 7-H, 11-H,
12-H, 13-H).
3H, CH ). Found, %: C 68.89; H 4.23; N 4.58;
3
S 10.72. C H NO S. Calculated, %: C 69.13; H 4.44;
N 4.74; S 10.86.
17
13
2
6-(4-Chlorobenzylideneamino)-2H-chromen-2-
one (XI). Yield 1.96 g (69%), mp 192–193°C.
1
6
-(4-Ethylbenzylideneamino)-2H-chromen-2-one
H NMR spectrum, δ, ppm (J, Hz): 6.455 d (1H, 3-H,
1
3
3
(
VI). Yield 1.94 g (70%), mp 168–169°C. H NMR
spectrum, δ, ppm (J, Hz): 6.443 d (1H, 3-H, J = 9.8),
.016 d (1H, 4-H, J = 9.7), 7.543 d (1H, 5-H, J =
.1), 7.483 d.d (1H, 7-H, J = 8.6, J = 1.4), 7.372 d
J = 9.5), 8.007 d (1H, 4-H, J = 9.5), 7.573 d (1H,
3
4
3
4
5-H, J = 2.3), 7.516 d.d (1H, 7-H, J = 8.8, J = 2.3),
3
4
3
8
1
(
1
7.388 d (1H, 8-H, J = 8.7), 8.653 s (1H, 9-H), 7.946 d
3
4
(2H, 10-H, 14-H), 7.516 d (2H, 11-H, 13-H). Found,
3
1H, 8-H, J = 8.9), 8.582 s (1H, 9-H), 7.837 d (2H,
0-H, 14-H), 7.321 d (2H, 11-H, 13-H), 2.714 q (2H,
CH ), 1.271 t (3H, CH ). Found, %: C 77.72; H 5.28;
%: C 67.59; H 3.27; Cl 12.39; N 4.75. C16
H10ClNO .
2
Calculated, %: C 67.74; H 3.55; Cl 12.50; N 4.94.
2
3
6-(4-Bromobenzylideneamino)-2H-chromen-2-
one (XII). Yield 2.36 g (72%), mp 188–189°C.
N 4.87. C H NO . Calculated, %: C 77.96; H 5.45;
18
15
2
1
N 5.05.
-(4-Acetaminobenzylideneamino)-2H-chromen-
-one (VII). Yield 2.11 g (69%), mp 232–234°C.
H NMR spectrum, δ, ppm (J, Hz): 6.454 d (1H, 3-H,
3
3
6
J = 9.5), 8.023 d (1H, 4-H, J = 9.5), 7.589 d (1H,
4
3
4
2
5-H, J = 1.9), 7.524 d.d (1H, 7-H, J = 9.0, J = 1.9),
7.391 d (1H, 8-H, J = 9.0), 8.648 s (1H, 9-H), 7.881 d
1
3
H NMR spectrum, δ, ppm (J, Hz): 6.436 d (1H, 3-H,
3
3
J = 9.5), 8.008 d (1H, 4-H, J = 9.5), 7.529 d (1H,
(2H, 10-H, 14-H), 7.668 d (2H, 11-H, 13-H). Found,
4
3
4
5
7
-H, J = 2.0), 7.472 d.d (1H, 7-H, J = 8.8, J = 2.0),
%: C 58.38; H 2.87; Br 24.17; N 4.06. C16
Calculated, %: C 58.56; H 3.07; Br 24.35; N 4.27.
-(4-Cyanobenzylideneamino)-2H-chromen-2-
H10BrNO .
2
3
.360 d (1H, 8-H, J = 8.7), 8.524 s (1H, 9-H), 7.830 d
(
(
2H, 10-H, 14-H), 7.718 d (2H, 11-H, 13-H), 2.086 s
6
3H, CH ), 10.088 s (1H, NH). Found, %: C 70.24;
one (XIII). Yield 2.06 g (75%), mp 250–251°C.
3
1
H 4.46; N 9.02. C H N O . Calculated, %: C 70.58;
1
8
14
2
3
H NMR spectrum, δ, ppm (J, Hz): 6.463 d (1H, 3-H,
3
3
H 4.61; N 9.15.
-[4-(5-Carboxy-1-methylpyrazol-3-yl)benzyli-
deneamino]-2H-chromen-2-one (VIIІ). Yield 2.80 g
J = 9.5), 8.031 d (1H, 4-H, J = 9.5), 7.638 s (1H,
3
5
-H), 7.572 d (1H, 7-H, J = 7.9), 7.410 d (1H, 8-H,
6
3
J = 7.9), 8.775 s (1H, 9-H), 7.908 d (2H, 10-H, 14-H),
.120 d (2H, 11-H, 13-H). Found, %: C 74.29; H 3.47;
N 10.04. C H N O . Calculated, %: C 74.45; H 3.67;
1
8
(
75%), mp 194–195°C. H NMR spectrum, δ, ppm
3
(
J, Hz): 6.444 d (1H, 3-H, J = 9.6), 8.013 d (1H, 4-H,
J = 9.6), 7.571 d (1H, 5-H, J = 2.0), 7.514 d.d (1H,
-H, J = 8.7, J = 2.0), 7.381 d (1H, 8-H, J = 8.7),
17 10
2
2
3
4
N 10.21.
3
4
3
7
6-(4-Nitrobenzylideneamino)-2H-chromen-2-one
1
8
.673 s (1H, 9-H), 8.044 d (2H, 10-H, 14-H), 7.381 d
(XIV). Yield 2.23 g (76%), mp 242–243°C. H NMR
3
(
(
2H, 11-H, 13-H), 7.541 d (1H, 4-H, pyrazolyl), 7.073 d
spectrum, δ, ppm (J, Hz): 6.471 d (1H, 3-H, J = 9.9),
3
1H, 5-H, pyrazolyl) 4.182 s (3H, CH ). Found, %:
8.040 d (1H, 4-H, J = 9.9), 7.676 c (1H, 5-H), 7.605 d
3
3
3
C 67.35; H 3.87; N 11.03. C H N O . Calculated, %:
(1H, 7-H, J = 9.4), 7.423 d (1H, 8-H, J = 9.4), 8.855 s
2
1
15
3
4
C 67.56; H 4.05; N 11.25.
(1H, 9-H), 8.205 d (2H, 10-H, 14-H), 8.348 d (2H,
1
1-H, 13-H). Found, %: C 65.13; H 3.21; N 9.39.
6
-(4-Benzoyloxybenzylideneamino)-2H-chro-
C H N O . Calculated, %: C 65.31; H 3.43; N 9.52.
men-2-one (ІX). Yield 2.58 g (70%), mp 216–217°C.
H NMR spectrum, δ, ppm (J, Hz): 6.444 d (1H, 3-H,
J = 9.6), 8.017 d (1H, 4-H, J = 9.6), 7.586 s (1H,
-H), 7.519 d (1H, 7-H, J = 8.5), 7.389 m (1H, 8-H),
.682 s (1H, 9-H), 8.052 d (2H, 10-H, 14-H), 7.389 d
2H, 11-H, 13-H), 8.168 d (2H, o-H), 7.586 d.d (2H,
m-H) 7.719 t (1H, p-H). Found, %: C 74.63; H 3.88;
16 10
2
4
1
6-(2-Hydroxybenzylideneamino)-2H-chromen-2-
one (XV). Yield 1.75 g (66%), mp 170–171°C.
3
3
3
1
5
8
(
H NMR spectrum, δ, ppm (J, Hz): 6.469 d (1H, 3-H,
J = 9.5), 8.035 d (1H, 4-H, J = 9.5), 7.740 d (1H,
3
3
4
3
4
5-H, J = 2.3), 7.663 d.d (1H, 7-H, J = 8.8, J = 2.3),
7.427 d (1H, 8-H, J = 8.8), 8.964 s (1H, 9-H), 6.949 d
3
N 3.58. C H NO . Calculated, %: C 74.79; H 4.09;
N 3.79.
(1H, 11-H), 7.383 d.d (1H, 12-H), 6.928 d.d (1H,
13-H), 7.605 d (1H, 14-H), 12.816 s (1H, OH).
2
3
15
4
6
-Benzylideneamino-2H-chromen-2-one (X).
6-(2-Ethoxybenzylideneamino)-2H-chromen-2-
one (XVI). Yield 2.05 g (70%), mp 173–175°C.
1
Yield 1.69 g (68%), mp 151–152°C. H NMR spec-
trum, δ, ppm (J, Hz): 6.449 d (1H, 3-H, J = 9.5),
.021 d (1H, 4-H, J = 9.8), 7.571 s (1H, 5-H, J =
.3), 7.384 d (1H, 8-H, J = 8.7), 8.636 s (1H, 9-H),
3
1
H NMR spectrum, δ, ppm (J, Hz): 6.442 d (1H, 3-H,
3
4
3
3
8
2
J = 9.7), 8.029 d (1H, 4-H, J = 9.5), 7.474 d (1H,
3
4
3
4
5-H, J = 2.1), 7.420 d.d (1H, 7-H, J = 8.7, J = 2.1),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 7 2005

1
068
GANUSHCHAK et al.
3
7
(
1
(
.367 d (1H, 8-H, J = 8.6), 8.886 s (1H, 9-H), 7.015 d
9-H), 7.219 s (2H, 10-H, 14-H), 3.781 s (3H, CH
3.891 s (6H, 2CH ). Found, %: C 66.85; H 4.93;
. Calculated, %: C 67.25; H 5.05;
3
),
1H, 11-H), 7.457 d.d (1H, 12-H), 7.068 d.d (1H,
3-H), 8.046 d (1H, 14-H), 4.170 q (2H, CH ), 1.451 t
3H, CH ). Found, %: C 73.52; H 4.93; N 4.63.
3
N 4.02. C19
N 4.13.
H17NO
5
2
3
C H NO . Calculated, %: C 73.71; H 5.15; N 4.78.
6-(4-Hydroxy-3-methoxybenzylideneamino)-2H-
chromen-2-one (XXIІ). Yield 2.63 g (89%), mp 193–
18
15
3
6
-(2-Fluorobenzylideneamino)-2H-chromen-2-
1
one (XVII). Yield 2.0 g (75%), mp 145–146°C.
194°C. H NMR spectrum, δ, ppm (J, Hz): 6.414 d
1
3
3
H NMR spectrum, δ, ppm (J, Hz): 6.442 d (1H, 3-H,
(1H, 3-H, J = 9.4), 7.970 d (1H, 4-H, J = 9.4),
3
3
3
J = 9.5), 8.021 d (1H, 4-H, J = 9.6), 7.597 d (1H,
7.468 s (1H, 5-H), 7.427 d (1H, 7-H, J = 8.5), 7.334 d
(1H, 8-H, J = 8.5), 8.418 s (1H, 9-H), 7.511 s (1H,
4
3
4
3
5
7
-H, J = 2.2), 7.509 d.d (1H, 7-H, J = 8.7, J = 2.2),
3
.377 d (1H, 8-H, J = 8.7), 8.824 s (1H, 9-H), 7.246 d
10-H), 6.860 d (1H, 13-H), 7.259 d (1H, 14-H),
(
1
1H, 11-H), 7.561 d.d (1H, 12-H), 7.307 d.d (1H,
3-H), 8.138 d (1H, 14-H). Found, %: C 71.75; H 3.62;
F 6.97; N 5.11. C H FNO . Calculated, %: C 71.91;
3.893 s (3H, OCH ), 9.519 s (1H, OH). Found, %:
3
C 68.89; H 4.25; N 4.67. C17H13NO . Calculated, %:
4
C 69.15; H 4.44; N 4.74.
1
6
10
2
H 3.77; F 7.11; N 5.24.
6-(3-Methoxy-4-propoxybenzylideneamino)-2H-
chromen-2-one (XXIIІ). Yield 2.63 g (78%), mp 197–
6
-(2-Chlorobenzylideneamino)-2H-chromen-2-
1
one (XVIII). Yield 1.93 g (68%), mp 181–183°C.
198°C. H NMR spectrum, δ, ppm (J, Hz): 6.439 d
1
3
3
H NMR spectrum, δ, ppm (J, Hz): 6.458 d (1H, 3-H,
J = 9.5), 8.046 d (1H, 4-H, J = 9.5), 7.597 s (1H,
(1H, 3-H, J = 9.3), 8.003 d (1H, 4-H, J = 9.5),
3
3
3
7.539 s (1H, 5-H), 7.463 d (1H, 7-H, J = 8.7), 7.370 d
(1H, 8-H, J = 8.2), 8.491 s (1H, 9-H), 7.514 s (1H,
3
3
5
-H), 7.518 d (1H, 7-H, J = 8.5), 7.411 d (1H, 8-H,
3
J = 8.5), 8.933 s (1H, 9-H), 7.327 d (1H, 11-H),
10-H), 6.990 d (1H, 13-H), 7.366 d (1H, 14-H), 4.000 t
7
.530 d.d (1H, 12-H), 7.365 d.d (1H, 13-H), 8.213 d
(2H, OCH
1.062 t (3H, CH
. Calculated, %: C 71.20; H 5.68; N 4.15.
6-(4-Benzoyloxy-3-methoxybenzylideneamino)-
2
), 3.882 s (3H, OCH
3 2
), 1.831 m (2H, CH ),
(
1H, 14-H). Found, %: C 67.59; H 3.37; Cl 12.37;
). Found, %: C 71.02; H 5.53; N 3.98.
3
N 4.79. C H ClNO . Calculated, %: C 67.74; H 3.55;
Cl 12.50; N 4.94.
C H19NO
20 4
16
10
2
6
-(2-Nitrobenzylideneamino)-2H-chromen-2-one
2H-chromen-2-one (XXIV). Yield 3.27 g (82%),
1
1
(
XIX). Yield 2.21 g (75%), mp 210–211°C. H NMR
spectrum, δ, ppm (J, Hz): 6.462 d (1H, 3-H, J = 9.6),
.066 d (1H, 4-H, J = 9.8), 7.625 d (1H, 5-H, J =
.2), 7.548 d.d (1H, 7-H, J = 8.7, J = 2.2), 7.420 d
1H, 8-H, J = 8.7), 8.951 s (1H, 9-H), 7.858 d (1H,
1-H), 7.769 d.d (1H, 12-H), 8.092 d.d (1H, 13-H),
.265 d (1H, 14-H). Found, %: C 65.12; H 3.26;
N 9.33. C H N O . Calculated, %: C 65.31; H 3.43;
mp 198–199°C. H NMR spectrum, δ, ppm (J, Hz):
3
3
3
6.451 d (1H, 3-H, J = 9.5), 8.024 d (1H, 4-H, J =
9.7), 7.564 m (5H, 5-H, 7-H, 14-H, m-H), 7.394 d (1H,
3
4
8
2
(
1
3
4
3
8-H, J = 8.8), 8.651 s (1H, 9-H), 7.751 s (1H, 10-H),
3
7.299 d (1H, 13-H), 3.907 s (3H, CH
), 8.150 d (2H,
3
o-H), 7.713 t (1H, p-H). Found, %: C 71.89; H 4.15;
8
N 3.43. C24
N 3.51.
H17NO . Calculated, %: C 72.17; H 4.29;
5
16
10
2
4
N 9.52.
-(2,4-Dimethylbenzylideneamino)-2H-chromen-
-one (XX). Yield 2.49 g (90%), mp 155–156°C.
6-[4-(4-Fluorobenzoyloxy)-3-methoxybenzyli-
6
deneamino]-2H-chromen-2-one (XXV). Yield 3.46 g
1
2
(83%), mp 198–199°C. H NMR spectrum, δ, ppm
1
3
H NMR spectrum, δ, ppm (J, Hz): 6.431 d (1H, 3-H,
(J, Hz): 6.448 d (1H, 3-H, J = 9.6), 8.017 d (1H, 4-H,
3
3
3
4
J = 9.6), 7.997 d (1H, 4-H, J = 9.7), 7.525 d (1H,
J = 9.6), 7.575 d (1H, 5-H, J = 2.3), 7.515 d.d (1H,
4
3
4
3
4
3
5
-H, J = 2.5), 7.470 d.d (1H, 7-H, J = 8.8, J = 2.5),
7-H, J = 8.8, J = 2.3), 7.389 d (1H, 8-H, J = 8.8),
3
7.356 d (1H, 8-H, J = 8.8), 8.768 s (1H, 9-H), 7.063 s
8.644 s (1H, 9-H), 7.746 s (1H, 10-H), 7.570 m (1H,
(
2
1H, 11-H), 7.093 d (1H, 13-H), 7.906 d (1H, 14-H),
14-H), 7.300 m (3H, 13-H, m-H), 3.902 s (3H, OCH
8.210 m (2H, o-H). Found, %: C 68.89; H 3.69;
F 4.43; N 3.19. C24 . Calculated, %: C 69.06;
H 3.86; F 4.55; N 3.36.
3
),
.366 s (3H, CH ), 2.584 s (3H, CH ). Found, %:
3
3
C 77.65; H 5.35; N 4.92. C H NO . Calculated, %:
H16FNO
5
1
8
15
2
C 77.96; H 5.45; N 5.05.
-(3,4,5-Trimethoxybenzylideneamino)-2H-chro-
men-2-one (XXІ). Yield 3.12 g (92%), mp 194–
1
(
6
6-(5-Bromo-2-methoxybenzylideneamino)-2H-
chromen-2-one (XXVI). Yield 3.37 g (94%), mp 184–
1
1
95°C. H NMR spectrum, δ, ppm (J, Hz): 6.437 d
185°C. H NMR spectrum, δ, ppm (J, Hz): 6.441 d
3
3
3
3
1H, 3-H, J = 9.4), 7.993 d (1H, 4-H, J = 9.6),
(1H, 3-H, J = 9.6), 8.021 d (1H, 4-H, J = 9.5), 7.526 d
4
3
4
3
4
7
8
.525 d (1H, 5-H, J = 2.1), 7.471 d.d (1H, 7-H, J =
.7, J = 2.2), 7.368 d (1H, 8-H, J = 8.6), 8.513 s (1H,
(1H, 5-H, J = 2.5), 7.456 d.d (1H, 7-H, J = 8.7, J =
4
3
3
2.5), 7.372 d (1H, 8-H, J = 8.7), 8.838 s (1H, 9-H),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 7 2005

SCHIFF BASES DERIVED FROM 6-AMINO-2H-CHROMEN-2-ONE.
1069
7
.093 d (1H, 11-H), 7.591 d.d (1H, 12-H), 8.144 d
C H ClFNO . Calculated, %: C 63.70; H 3.01;
1
6
9
2
(
1H, 14-H), 3.928 s (3H, OCH ). Found, %: C 56.69;
Cl 11.75; F 6.30; N 4.64.
3
H 3.21; Br 21.98; N 3.78. C H BrNO . Calculated,
1
7
12
3
6-[3-Methoxy-4-(5-carboxy-1-methylpyrazolyl)-
%
: C 57.01; H 3.38; Br 22.31; N 3.91.
-(2-Hydroxy-3,5-dichlorobenzylideneamino)-
H-chromen-2-one (XXVII). Yield 2.97 g (89%),
benzylideneamino]-2H-chromen-2-one (XXXII).
1
6
Yield 2.78 g (69%), mp 215–217°C. H NMR spec-
3
2
trum, δ, ppm (J, Hz): 6.451 d (1H, 3-H, J = 9.5),
1
3
mp 230–231°C. H NMR spectrum, δ, ppm (J, Hz):
8.032 d (1H, 4-H, J = 9.5), 7.550 m (4H, 5-H, 7-H,
3
3
3
1
8
1
4-H; 4-H, pyrazolyl), 7.393 d (1H, 8-H, J = 8.7),
.651 s (1H, 9-H), 7.751 s (1H, 10-H), 7.301 d (1H,
3-H), 7.059 d (1H, 5-H, pyrazolyl), 4.176 s (3H,
6.491 d (1H, 3-H, J = 9.4), 8.050 d (1H, 4-H, J =
4
9
.6), 7.818 d (1H, 5-H, J = 2.5), 7.736 d.d (1H, 7-H,
3
4
3
J = 8.8, J = 2.5), 7.468 d (1H, 8-H, J = 8.7), 9.068 s
NCH ), 3.922 s (3H, OCH ). Found, %: C 65.32;
(
1H, 9-H), 7.541 s (1H, 12-H), 7.672 s (1H, 14-H),
3
3
H 4.12; N 10.18. C H N O . Calculated, %: C 65.51;
1
4.010 s (1H, OH). Found, %: C 57.23; H 2.49;
22 17
3
5
H 4.25; N 10.42.
Cl 20.93; N 4.02. C H Cl NO . Calculated, %:
1
6
9
2
3
C 57.51; H 2.71; Cl 21.22; N 4.19.
-(3-Nitrobenzylideneamino)-2H-chromen-2-one
6-(2-Hydroxy-1-naphthylmethylideneamino)-
2
H-chromen-2-one (XXXIII). Yield 2.33 g (74%),
6
1
mp 220–221°C. H NMR spectrum, δ, ppm (J, Hz):
(
XXVIII). Yield 2.23 g (76%), mp 214–215°C.
3
3
1
6.477 d (1H, 3-H, J = 9.6), 8.028 d (1H, 4-H, J =
H NMR spectrum, δ, ppm (J, Hz): 6.459 d (1H, 3-H,
J = 7.9), 8.021 d (1H, 4-H, J = 8.3), 7.646 s (1H,
4
3
3
9.5), 7.937 d (1H, 5-H, J = 2.4), 7.843 d.d (1H, 7-H,
3
4
3
3
J = 8.8, J = 2.4), 7.437 d (1H, 8-H, J = 8.8), 9.714 s
(1H, 9-H), 7.045 d (1H, 3-H, naphthyl), 7.60 m (4H,
-H, 5-H, 6-H, 7-H, naphthyl), 8.469 d (1H, 8-H,
5
-H), 7.584 d (1H, 7-H, J = 7.6), 7.405 d (1H, 8-H,
3
J = 7.9), 8.851 s (1H, 9-H), 8.766 s (1H, 10-H),
4
7
.792 d.d (1H, 13-H), 8.344 d (2H, 12-H, 14-H).
naphthyl), 15.464 s (1H, OH). Found, %: C 76.12;
H 4.05; N 4.35. C H NO . Calculated, %: C 76.18;
Found, %: C 64.98; H 3.15; N 9.33. C H N O . Cal-
1
6
10
2
4
2
0
13
3
culated, %: C 65.31; H 3.43; N 9.52.
-(4-Chloro-3-nitrobenzylideneamino)-2H-chro-
men-2-one (XXIX). Yield 2.53 g (78%), mp 247–
H 4.16; N 4.44.
6
6
-(9-Anthrylmethylideneamino)-2H-chromen-2-
one (XXXIV). Yield 3.0 g (86%), mp 247–248°C.
1
2
(
(
48°C. H NMR spectrum, δ, ppm (J, Hz): 6.449 d
1
H NMR spectrum, δ, ppm (J, Hz): 6.486 d (1H, 3-H,
3
3
1H, 3-H, J = 9.4), 8.003 d (1H, 4-H, J = 9.4), 7.626 s
1H, 5-H), 7.567 d (1H, 7-H, J = 8.2), 7.397 d (1H,
-H, J = 8.2), 8.797 s (1H, 9-H), 8.531 s (1H, 10-H),
3
3
J = 9.5), 8.094 d (1H, 4-H, J = 9.8), 7.822 d (1H,
3
4
3
4
5
7
(
7
6
-H, J = 2.5), 7.740 d.d (1H, 7-H, J = 8.7, J = 2.5),
3
8
3
.472 d (1H, 8-H, J = 8.7), 9.838 s (1H, 9-H), 8.718 s
7
.831 d (1H, 13-H), 8.221 d (1H, 14-H). Found, %:
1H, 10-H, anthryl), 8.894 d (2H, 1-H, 8-H, anthryl),
.612 d.d (2H, 2-H, 7-H, anthryl), 7.555 d.d (2H, 3-H,
-H, anthryl), 8.131 d (2H, 4-H, 5-H, anthryl). Found,
C 58.29; H 2.59; Cl 10.65; N 8.34. C H ClN O . Cal-
1
6
9
2
4
culated, %: C 58.46; H 2.76; Cl 10.79; N 8.52.
-(2-Chloro-5-nitrobenzylideneamino)-2H-chro-
men-2-one (XXX). Yield 2.99 g (91%), mp 262–
6
%: C 82.35; H 4.17; N 3.79. C H NO . Calculated,
24 15 2
%
: C 82.51; H 4.33; N 4.01.
-(3-Pyridylmethylideneamino)-2H-chromen-
-one (XXXV). Yield 1.95 g (78%), mp 162–163°C.
1
2
(
7
8
63°C. H NMR spectrum, δ, ppm (J, Hz): 6.475 d
6
3
3
1H, 3-H, J = 9.6), 8.056 d (1H, 4-H, J = 9.5),
.737 d (1H, 5-H, J = 2.0), 7.632 d.d (1H, 7-H, J =
.7, J = 2.0), 7.433 d (1H, 8-H, J = 8.7), 8.998 s
2
4
3
1
H NMR spectrum, δ, ppm (J, Hz): 6.446 d (1H, 3-H,
4
3
3
3
J = 9.5), 8.011 d (1H, 4-H, J = 9.4), 7.601 s (1H,
(
8
1H, 9-H), 7.853 d (1H, 11-H), 8.356 d.d (1H, 12-H),
.961 d (1H, 14-H). Found, %: C 58.32; H 2.63;
Cl 10.63; N 8.31. C H ClN O . Calculated, %:
5
8
-H), 7.523 m (2H, 7-H; 5-H, pyridyl), 7.385 d (1H,
3
-H, J = 8.8), 9.032 s (1H, 9-H), 8.662 d (1H, 4-H,
1
6
9
2
4
pyridyl), 8.300 d (1H, 6-H, pyridyl), 8.736 s (1H, 2-H,
pyridyl). Found, %: C 71.89; H 3.87; N 10.98.
C 58.46; H 2.76; Cl 10.79; N 8.52.
6
-(2-Chloro-6-fluorobenzylideneamino)-2H-chro-
C H N
15 10 2
O
2
. Calculated, %: C 71.99; H 4.03; H 11.19.
men-2-one (XXXI). Yield 2.20 g (73%), mp 164°C.
6-(2-Hydroxy-6-methylquinolin-3-ylmethyli-
1
H NMR spectrum, δ, ppm (J, Hz): 6.453 d (1H, 3-H,
deneamino)-2H-chromen-2-one (XXXVI). Yield
3
3
1
J = 9.5), 8.043 d (1H, 4-H, J = 9.5), 7.577 d (1H,
2.31 g (70%), mp 331–332°C. H NMR spectrum, δ,
4
3
4
3
5
7
-H, J = 2.5), 7.490 d.d (1H, 7-H, J = 8.7, J = 2.5),
ppm (J, Hz): 6.438 d (1H, 3-H, J = 9.1), 8.051 d (1H,
3
3
.403 d (1H, 8-H, J = 8.7), 8.777 s (1H, 9-H), 7.275 m
4-H, J = 9.4), 7.599 s (1H, 5-H), 7.508 d (1H, 7-H,
3
3
(1H, 11-H), 7.540 m (1H, 12-H), 7.395 m (1H, 13-H).
J = 9.0), 7.380 d (1H, 8-H, J = 9.0), 8.865 s (1H,
9-H), 8.574 s (1H, 4-H, quinolyl), 7.542 s (1H, 5-H,
Found, %: C 63.42; H 2.83; Hlg 17.85; N 4.23.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 7 2005

1
070
GANUSHCHAK et al.
quinolyl), 7.262 d (1H, 7-H, quinolyl), 7.346 d (1H,
REFERENCES
8
-H, quinolyl), 2.404 s (3H, CH ), 12.029 s (1H, OH).
3
1
. Christie, R.M. and Chih-Hung, L., Dyes Pigm., 1999,
vol. 42, p. 85.
Found, %: C 72.57; H 4.07; N 8.26. C H N O . Cal-
culated, %: C 72.72; H 4.27; N 8.48.
2
0
14
2
3
2
. Urano, T., Nagasaka, H., Tsuchiyama, M., Shimizu, S.,
Kawazoe, K., Shimizu, M., and Yamaoka, T., Bull.
Chem. Soc. Jpn., 1995, vol. 68, p. 1661.
6
-(2-Methylindol-3-ylmethylideneamino)-2H-
chromen-2-one (XXXVII). Yield 1.75 g (58%),
mp 215–216°C. H NMR spectrum, δ, ppm (J, Hz):
1
3
4
5
. Zhang, Y.-Y., Meng, X.-M., Wang, X.-L., and Xu, L.-H.,
3
3
6
9
7
.406 d (1H, 3-H, J = 9.4), 7.984 d (1H, 4-H, J =
Dyes Pigm., 2003, vol. 56, p. 189.
3
.4), 7.587 s (1H, 5-H), 7.456 d (1H, 7-H, J = 8.5),
. Nishizono, N., Oda, K., Ohno, K., Minami, M., and
3
.330 d (1H, 8-H, J = 8.5), 8.737 s (1H, 9-H), 7.356 d
Machida, M., Heterocycles, 2001, vol. 55, p. 1897.
(
7
1H, 4-H, indolyl), 7.125 d.d (1H, 5-H, indolyl),
.094 d.d (1H, 6-H, indolyl), 8.334 d (1H, 7-H,
indolyl), 2.676 s (3H, CH ), 11.557 s (1H, NH). Found,
. Kachkovski, O.D., Tolmachev, O.I., Kobryn, L.O.,
Vіla, E.E., and Ganushchak, M.I., Dyes Pigm., 2004,
vol. 63, p. 203.
3
%
: C 75.34; H 4.32; N 9.06. C H N O . Calculated,
6. Morgan, G.T. and Micklethwait, F.M.G., J. Chem. Soc.,
1
9
14
2
2
%
: C 75.48; H 4.67; N 9.27.
-(1,2-Dimethylindol-3-ylmethylideneamino)-
H-chromen-2-one (XXXVIII). Yield 1.99 g (63%),
1904, vol. 85, p. 1230.
7
. Trkovnik, M., Bobarevic, B., and Hadzimusic, M., Glas.
Hem. Tehnol, Bosne Hercegovine, 1968, vol. 16, p. 117;
Chem. Abstr., 1970, vol. 72, p. 43344u.
6
2
1
mp 219–220°C. H NMR spectrum, δ, ppm (J, Hz):
3
3
8. Karpyak, V.V., Obushak, N.D., Mizyuk, V.L., and Ganu-
6
9
7
.402 d (1H, 3-H, J = 9.4), 7.970 d (1H, 4-H, J =
.4), 7.490 s (1H, 5-H), 7.479 d (1H, 7-H, J = 8.5),
.399 d (1H, 8-H, J = 8.5), 8.765 s (1H, 9-H), 7.325 d
shchak, N.I., Russ. J. Org. Chem., 2000, vol. 36, p. 83.
3
3
9. Gordon, A.J. and Ford, R.A., The Chemist's Companion,
New York: Wiley, 1972. Translated under the title
Sputnik khimika, Moscow: Mir, 1976, p. 167.
0. Hammett, L., Physical Organic Chemistry, New York:
McGraw–Hill, 1970, 2nd ed. Translated under the title
Osnovy fizicheskoi organicheskoi khimii, Moscow: Mir,
1972, p. 476.
(
7
1H, 4-H, indolyl), 7.146 d.d (1H, 5-H, indolyl),
.195 d.d (1H, 6-H, indolyl), 8.395 d (1H, 7-H, in-
dolyl), 3.754 s (3H, NCH ), 2.682 s (3H, CH ). Found,
1
3
3
%: C 75.73; H 4.89; N 8.73. C H N O . Calculated,
20 16 2 2
%: C 75.93; H 5.10; N 8.85.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 7 2005