Functionalization of oxadiazolylindole systems

Article abstract of DOI:10.1134/S1070428009050121

A new synthetic approach was developed to the preparation of functional derivatives of 3-(1,3,4-oxadiazol-2-yl)-1H-indoles starting with a synthetically available 3-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1H-indole. The versatility of the developed strate

Full text of DOI:10.1134/S1070428009050121

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 5, pp. 719−724. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © S.B. Alyab’ev, D.V. Kravchenko, A.V. Ivashchenko, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 5,
pp. 734−739.
Functionalization of Oxadiazolylindole Systems
S. B. Alyab’ev, D. V. Kravchenko, andA. V. Ivashchenko
Research Institute of Chemical Diversity
Khimki, Moscow oblast, 141400 Russia; e-mail: alyabjev@iihr.ru
Received August 13, 2008
Abstract—A new synthetic approach was developed to the preparation of functional derivatives of 3-(1,3,4-
oxadiazol-2-yl)-1H-indoles starting with a synthetically available 3-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1H-indole.
The versatility of the developed strategy was demonstrated in the synthesis of this kind compounds with a wide
range of substituents.
DOI: 10.1134/S1070428009050121
In the method reported here of the synthesis of
3-(1,3,4-oxadiazol-2-yl)-1H-indoles as well as in a number
of methods previously described [4, 5] the key reaction
consists in the condensation of methyl 1H-indole-3-
carboxyimidoate hydrochloride with chloroacetic acid
iminoester affording the skeleton of the target structures.
Indoles and their derivatives underlie many natural and
synthetic compounds endowed with a wide range of
biological action. In particular, among them substances
were found exhibiting fungicidal properties [1], compounds
simulating the recognition sites on the membranes of brain
cells [2]. Some 5-mercapto derivatives of 3-(1,3,4-
oxadiazol-2-yl)-1H-indoles possess bactericidal qualities
[3]. These examples show that the heterocyclic structures
containing the 3-(1,3,4-oxadiazol-2-yl)-1H-indole
fragment belong to an important class of compounds with
a wide range of biological action that can be extended by
the synthesis of new compounds of this type. The
development of efficient approaches to the synthesis of
these structure will favorably affect the creation of new
physiologically active substances.
We chose as the initial reagent the synthetically
available 3-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1H-
indole (I) prepared from 1H-indole-3-carboxylic acid
hydrazide (II) [4]. We developed a sequence of synthetic
stages occurring with medium and high yields at a wide
range of substituents.
In the first stage of the study we synthesized along
the known method [6, 7] in 72–78% yields 2-methylene-
Scheme 1.
R1
Cl
N
R2
N
N
N
NH2
NH
O
O
O
N
HNR1R2
DMSO
ClCH2C(NH)OMe
K2CO3, DMF
N
N
N
H
H
H
IIIa_IIId
I
II
R1,R2 = morpholin-4-yl (a), pyrrolidin-1-yl (b), piperidin-1-yl (c), 4-methylpiperidin-1-yl (d).
719

ALYAB’EV et al.
720
The employed amidation method is of a general character
unlke, e.g., the preparation of amides via the correspond-
ing esters IV. We failed to obtain target reaction products
VI attempting to prepare them by the latter method using
certain aromatic and heteroaromatic amines, or the
reaction did not result in the complete conversion of ester
IV into the amide, and it decreased the yield of compound
VI and required its additional purification.
amino derivatives of 5-(1H-indole-3-yl)-1,3,4-oxadiazol
(III) (Scheme 1).
The published methods of the preparation of 3-(1,3,4-
oxadiazol-2-yl)-1H-indoles N-alkyl derivatives involve the
indole system alkylation at the starting stages of the
synthesis before the formation of the oxadiazole ring. In
particular FarghalyAbdel-Rahman [8] used this approach
in the synthesis of 1-benxyl-3-[1,3,4]oxadiazol-2-yl-1H-
indole. The known preparation method of 1-methyl-3-(5-
pyridin-4-yl[1,3,4]oxadiazol-2-yl)-1H-indole [2] also
consisted in a similar approach. The first stage in this
synthetic route involved the methylation of the indole
system with dimethyl sulfate [9]. We showed for the first
time that 3-(1,3,4-oxadiazol-2-yl)-1H-indoles could be
alkylated with methyl chloroacetate obtaining the target
esters in high yields (Scheme 2).
The structure and the composition of all compounds
1
synthesized were confirmed by H NMR spectra and
elemental analyses. The purity of compounds and their
molecular mass were determined by HPLC-MS method.
The general procedure and the most typical examples of
amides VI syntheses are presented in EXPERIMENTAL.
The detailed characteristics of the other amides of this
series are available from the authors.
The developed synthetic strategy can be efficiently
used for creating large combinatorial libraries. The devel-
oped procedures can be easily reproduced on large amounts
of reagents. The relatively mild reaction conditions, the
easy separation and relatively high yields of the target
products in the described approach make it a powerful
tool in the combinatorial chemistry. The developed
synthetic approach provides a possibility of the preparation
of a great versatility of new potentially biologically active
polysubstituted 3-(1,3,4-oxadiazol-2-yl)-1H-indoles.
Esters IVa–IVd obtained were converted in high
yields under mild conditions into the corresponding acids
Va–Vd. The hydrolysis was performed in the THF–water
mixture with lithium hydroxide followed by the treatment
with the hydrochloric acid. The acids obtained were used
in further stage without additional purification. The
amination of acids Va–Vd under mild conditions gave a
wide range of the corresponding amides VI (Scheme 3).
The amination was successfully carried out involving
various linear and branched aliphatic VIIa–VIIf, alicyclic
VIIIa–VIIIe, aromatic amines like phenylalkylamines
IXa–IXe and substituted anilines Xa–Xe, heterocyclic
XIa–XIf and heteroaromatic XIIa–XIIe amines.
EXPERIMENTAL
Thin layer chromatography was performed on
Kieselgel 60 F-254 plates. 1H NMR spectra from solutions
of studied compounds in DMSO-d6 were registered on
The preparation of amides VI from the corresponding
acids V was carried out by the classic procedure applying
carbonyldiimidazole (CDI) as the carboxy group activator.
Scheme 2.
R1
R1
N
R2
N
R2
N
N
N
O
O
N
(1) LiOH_THF_H2O
(2) HCl_H2O
ClCH2COOMe
K2CO3, DMF
IIIa_IIId
N
N
O
O
OMe
IVa_IVd
OH
Va_Vd
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FUNCTIONALIZATION OF OXADIAZOLYLINDOLE SYSTEMS
721
Scheme 3.
R1
N
R2
N
O
N
CDI
Va_Vf
+
HNR3R4
DMSO
N
VIIa_VIIe, VIIIa_VIIIf_Xa_Xf,
O
XIa_XIe, XIIa_XIIf
N
R3
R4
VI
O
H
N
(d),
(e),
(b),
(c),
(f);
(a),
VII:
N
N
H
NH2
H2N
O
OEt
N
NH2
NH2
(e);
(a),
NH2
(b),
NH2
(c),
(d),
NH2
VIII:
EtO
NH2
NH2
O
S
H
N
O
(a),
NH2
(b),
NH2
(c),
NH2
(e);
IX:
H2N
(d),
Cl
NH2
H2N
(b),
H2N
MeO
NH2
H2N
O
(e);
(a),
(c),
(d),
X:
OEt MeO
O
Cl
O
O
O
(d),
(e),
NH
(a),
(c),
(f);
(b),
HN
O
XI:
N
NH
N
NH
HN
O
N
H
H2N
(d),
N
OMe
(e).
N N
N
N
O
H2N
(b),
H2N
(a),
(c),
XII:H2N
H2N
O
S
N
H
a spectrophotometric detector operating on wavelengths
max. 220 and 254 nm. According to the HPLC-MS data
the purity of all compounds obtained exceeded 95%. All
the solvents and reagents used in the study were
a spectrometer Bruker DPX-400 (400.1300 MHz, 25°C),
internal reference TMS. Spectra HPLC-MS were obtain-
ed with the use of liquid chromatograph PE SCIEX API
150EX equipped with a column C18 (100 × 4 mm) and
λ
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 5 2009

ALYAB’EV et al.
722
purchased from Acros Organics, Aldrich, and ChemDiv
and were applied without additional purification.
chloroacetate and 0.14 mol of calcined K2CO3. The
reaction mixture was heated at 50°C for 3 h, then it was
cooled to room temperature and poured into cold water
at vigorous stirring. The formed precipitate was filtered
off, washed with cold water and hexane.
3-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-1H-
1
indole (I) [4]. Yield 93%, mp 212–214°C. H NMR
spectrum, δ, ppm: 7.22–7.32 m (2H, Ar), 7.52–7.58 m
(1H, Ar), 8.07–8.13 m (1H, Ar), 8.21 d (1H, C2H,
J 2.9 Hz), 12.07 br.s (1H, NH). Mass spectrum: m/z 235
[M + 1]+. Found, %: C 56.66; H 3.51; Cl 15.09; N 18.10.
C11H8ClN3O. Calculated, %: C 56.54; H 3.45; Cl 15.17;
N 17.98.
Methyl 3-[5-(morpholin-4-ylmethyl)-1,3,4-oxa-
diazol-2-yl]-1H-indole-1-acetate (IVa). Yield 74%, mp
1
130–132°C. H NMR spectrum, δ, ppm: 2.56–2.62 m
[4H, N(CH2)2], 3.60–3.65 m [4H, O(CH2)2], 3.76 s (3H,
OCH3), 3.82 s (2H, CH2), 5.27 s (2H, CH2COOMe),
7.25–7.33 m (2H, Ar), 7.51–7.56 m (1H, Ar), 8.09–
8.13 m (1H, Ar), 8.14 s (1H, C2H). Mass spectrum: m/z
357 [M + 1]+. Found, %: C 60.84; H 5.61; N 15.79.
C18H20N4O4. Calculated, %: C 60.66; H 5.66; N 15.72.
3-[5-(Morpholin-4-ylmethyl)-1,3,4-oxadiazol-2-
yl]-1H-indole (IIIa) [6]. Yield 77%, mp 179–181°C.
1H NMR spectrum, δ, ppm: 2.52–2.59 m [4H, N(CH2)2],
3.58–3.65 m [4H, O(CH2)2], 3.84 s (2H, CH2), 7.19–
7.28 m (2H, Ar), 7.51–7.58 m (1H, Ar), 8.07–8.13 m
(2H, C2H and Ar), 11.87 br.s (1H, NH). Mass spectrum:
m/z 285 [M + 1]+. Found, %: C 63.48; H 5.71; N 19.89.
C15H16N4O2. Calculated, %: C 63.37; H 5.67; N 19.71.
Methyl 3-[5-(pyrrolidin-1-yl-methyl)-1,3,4-oxa-
diazol-2-yl]-1H-indole-1-acetate (IVb). Yield 80%, mp
1
142–144°C. H NMR spectrum, δ, ppm: 1.75–1.83 m
[4H, (CH2)2], 2.62–2.70 m [4H, N(CH2)2], 3.78 s (3H,
OCH3), 3.88 s (2H, CH2), 5.24 s (2H, CH2COOMe),
7.22–7.32 m (2H, Ar), 7.50–7.56 m (1H, Ar), 8.08–
8.12 m (1H, Ar), 8.16 s (1H, C2H). Mass spectrum: m/z
341 [M + 1]+. Found, %: C 63.58; H 5.99; N 16.44.
C18H20N4O3. Calculated, %: C 63.52; H 5.92; N 16.46.
3-[5-(Pyrrolidin-1-ylmethyl)-1,3,4-oxadiazol-2-
yl]-1H-indole (IIIb) [6]. Yield 91%, mp 176–178°C.
1H NMR spectrum, δ, ppm: 1.74–1.81 m [4H, (CH2)2],
2.60–2.68 m [4H, N(CH2)2], 3.91 s (2H, CH2), 7.16–
7.27 m (2H, Ar), 7.48–7.54 m (1H, Ar), 8.03–8.12 m
(2H, C2H and Ar), 11.88 br.s (1H, NH). Mass spectrum:
m/z 269 [M + 1]+. Found, %: C 67.18; H 6.12; N 20.89.
C15H16N4O. Calculated, %: C 67.15; H 6.01; N 20.88.
Methyl 3-[5-(piperidin-1-yl-methyl)-1,3,4-oxa-
diazol-2-yl]-1H-indole-1-acetate (IVc). Yield 67%, mp
1
134–136°C. H NMR spectrum, δ, ppm: 1.38–1.46 m
(2H, CH2), 1.53–1.61 m [4H, (CH2)2], 2.48–2.54 m [4H,
N(CH2)2], 3.74 s (3H, OCH3), 3.80 s (2H, CH2), 5.27 s
(2H, CH2COOMe), 7.24–7.34 m (2H, Ar), 7.50–7.55 m
(1H, Ar), 8.12–8.15 m (1H, Ar), 8.17 C (1H, C2H). Mass
spectrum: m/z 355 [M + 1]+. Found, %: C 64.48; H 6.29;
N 15.88. C19H22N4O3. Calculated, %: C 64.39; H 6.26;
N 15.81.
3-[5-(Piperidin-1-ylmethyl)-1,3,4-oxadiazol-2-yl]-
1H-indole (IIIc) [6]. Yield 97%, mp 186–188°C.
1H NMR spectrum, δ, ppm: 1.36–1.46 m (2H, CH2), 1.51–
1.61 m [4H, (CH2)2], 2.47–2.53 m [4H, N(CH2)2], 3.77 s
(2H, CH2), 7.16–7.27 m (2H,Ar), 7.48–7.54 m (1H, Ar),
8.03–8.12 m (2H, C2H and Ar), 11.94 br.s (1H, NH).
Mass spectrum, m/z 283 [M + 1]+. Found, %: C 68.13;
H 6.49; N 19.99. C16H18N4O. Calculated, %: C 68.06;
H 6.43; N 19.84.
Methyl 3-{5-[(4-methyl-1-piperidinyl)methyl]-
1,3,4-oxadiazol-2-yl}-1H-indole-1-acetate (IVd).
Yield 87%, mp 127–129°C. 1H NMR spectrum, δ, ppm:
0.91 d (3H, CH3, J 6.4 Hz), 1.14–1.27 m (2H, CH2),
1.28–1.40 m (1H, CH), 1.58–1.65 m (2H, CH2), 2.10–
2.19 m (2H, CH2), 2.86–2.92 m (2H, CH2), 3.73 s (3H,
OCH3), 3.80 s (2H, CH2), 5.25 s (2H, CH2COOMe),
7.24–7.32 m (2H, Ar), 7.48–7.54 m (1H, Ar), 8.11–
8.13 m (1H, Ar), 8.15 s (1H, C2H). Mass spectrum: m/z
369 [M + 1]+. Found, %: C 65.24; H 6.69; N 15.29.
C20H24N4O3. Calculated, %: C 65.20; H 6.57; N 15.21.
3-[5-(4-Methylpiperidin-1-ylmethyl)-1,3,4-
oxadiazol-2-yl]-1H-indole (IIId) [6]. Yield 94%, mp
171–173°C. 1H NMR spectrum, δ, ppm: 0.92 d (3H, CH3,
J 6.4 Hz), 1.14–1.27 m (2H, CH2), 1.30–1.40 m (1H,
CH), 1.58–1.65 m (2H, CH2), 2.10–2.19 m (2H, CH2),
2.86–2.92 m (2H, CH2), 3.79 s (2H, CH2), 7.18–7.27 m
(2H, Ar), 7.49–7.53 m (1H, Ar), 8.06 s (1H, C2H), 8.08–
8.12 m (2H, Ar), 11.92 br.s (1H, NH). Mass spectrum,
m/z 297 [M + 1]+. Found, %: C 68.93; H 6.94; N 18.99.
C17H20N4O. Calculated, %: C 68.89; H 6.80; N 18.90.
Acids Va–Vd. General procedure. To a solution of
0.1 mol of ester IVa–IVd in 100 ml of THF was added
a solution of 0.12 mol of lithium hydroxide in 25 ml of
water. The reaction mixture was kept for 3–4 h at room
Methyl esters IVa–IVd. General procedure. To
a solution of 0.1 mol of compound IIIa–IIId in 110 ml of
anhydrous DMF was added 0.12 mol of methyl
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FUNCTIONALIZATION OF OXADIAZOLYLINDOLE SYSTEMS
723
temperature while vigorous stirring [TLC monitoring,
(EtOH–CH2Cl2, 5 : 95)]. The reaction mixture was diluted
with water, and concn. HCl was added till pH 2. The
separated precipitate was filtered off, washed with a little
of ice water, with ethanol, and hexane.
mmol of amine VII–XII. The reaction mixture was stirred
for 3–4 h at 60°C, cooled to room temperature, and poured
into cold water. The separated precipitate was filtered
off, washed with water and hexane. The oily substance
was extracted into ethyl acetate, the extract was washed
with a NaCl solution and with water, and dried with
Na2SO4. On removing the solvent under a reduced pres-
sure the reaction products was purified by crystallization
from a mixture benzene–hexane or from isooctane, or
by column chromatography on silica gel, eluent ethyl
acetate–hexane, 25:75.
3-[5-(Morpholin-4-ylmethyl)-1,3,4-oxadiazol-2-
yl]-1H-indole-1-acetic acid (Va). Yield 69%, mp 239–
1
241°C. H NMR spectrum, δ, ppm: 2.70–2.80 m [4H,
N(CH2)2], 3.90–4.02 m [4H, O(CH2)2], 4.77 s (2H,
CH2), 5.22 s (2H, CH2COOH), 7.28–7.36 m (2H, Ar),
7.55–7.60 m (1H, Ar), 8.15–8.19 m (1H,Ar), 8.24 s (1H,
C2H), 11.54 br.s (1H, COOH). Mass spectrum: m/z 343
[M + 1]+. Found, %: C 59.74; H 5.33; N 16.59.
C17H18N4O4. Calculated, %: C 59.64; H 5.30; N 16.37.
N-{[4-(Methylthio)phenyl]methyl-3-[5-(morpho-
lin-4-ylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indol-1-
yl}acetamide (VIa). Yield 84%, mp 152–154°C. 1H NMR
spectrum, δ, ppm: 2.46 s (3H, SCH3), 2.55–2.63 m [4H,
N(CH2)2], 3.62–3.69 m [4H, O(CH2)2], 3.84 s (2H,
CH2), 4.28 d (2H, NHCH2, J 5.9 Hz), 4.97 s (2H,
CH2CONH), 7.17–7.23 m (4H, Ar), 7.24–7.33 m (2H,
Ar), 7.46–7.52 m (1H, Ar), 8.07–8.11 m (1H, Ar), 8.13 s
(1H, C2H), 8.68 t (1H, NH, J 5.9 Hz). Mass spectrum:
m/z 479 [M + 1]+. Found, %: C 62.74; H 5.93; N 14.60.
C25H27N5O3S. Calculated, %: C 62.87; H 5.70; N 14.66.
3-[5-(Pyrrolidin-1-ylmethyl)-1,3,4-oxadiazol-2-
yl]-1H-indole-1-acetic acid (Vb). Yield 88%, mp 249–
1
251°C. H NMR spectrum, δ, ppm: 1.99–2.11 m [4H,
(CH2)2], 3.59–3.66 m [4H, N(CH2)2], 4.71 b (2H, CH2),
5.20 b (2H, CH2COOH), 7.26–7.35 m (2H, Ar), 7.56–
7.61 m (1H,Ar), 8.14–8.20 m (1H,Ar), 8.26 b (1H, C2H),
11.70 br.s (1H, COOH). Mass spectrum: m/z 327 [M +
1]+. Found, %: C 62.68; H 5.59; N 17.21. C17H18N4O3.
Calculated, %: C 62.57; H 5.56; N 17.17.
N-Methyl-N-benzyl-{3-[5-(pyrrolidin-1-yl-
methyl)-1,3,4-oxadiazol-2-yl]-1H-indol-1-yl}-
acetamide (VIb). Yield 58%, mp 117–119°C. 1H NMR
spectrum, δ, ppm: 1.76–1.84 m [4H, (CH2)2], 2.67–
2.74 m [4H, N(CH2)2], 3.10 s (3H, NCH3), 3.88 s (2H,
CH2), 4.55 s (2H, NCH2), 4.94 s (2H, CH2CON), 7.20–
7.40 m (7H, Ar), 7.50–7.56 m (1H, Ar), 8.06–8.11 m
(1H, Ar), 8.14 s (1H, C2H). Mass spectrum: m/z 431
[M + 1]+. Found, %: C 69.97; H 6.33; N 16.39.
C25H27N5O2. Calculated, %: C 69.91; H 6.34; N 16.31.
3-[5-(Piperidin-1-ylmethyl)-1,3,4-oxadiazol-2-yl]-
1H-indole-1-acetic acid (Vc). Yield 67%, mp 224–
1
227°C. H NMR spectrum, δ, ppm: 1.80–1.90 m [4H,
(CH2)2], 3.05–3.20 m (2H, NCH2), 3.50–3.67 m (2H,
NCH2), 4.73 s (2H, CH2), 5.23 s (2H, CH2COOH),
7.27–7.36 m (2H, Ar), 7.57–7.61 m (1H, Ar), 8.16–
8.20 m (1H, Ar), 8.25 s (1H, C2H), 11.60 br.s (1H,
COOH). Mass spectrum: m/z 341 [M + 1]+. Found, %:
C 63.55; H 5.96; N 16.49. C18H20N4O3. Calculated, %:
C 63.52; H 5.92; N 16.46.
N-Cycloheptyl-{3-[5-(piperidin-1-ylmethyl)-
1,3,4-oxadiazol-2-yl]-1H-indol-1-yl}acetamide (VIc).
3-{5-[(4-Methylpiperidin-1-yl)methyl]-1,3,4-
oxadiazol-2-yl}-1H-indole-1-acetic acid (Vd). Yield
93%, mp 231–233°C. 1H NMR spectrum, δ, ppm: 0.93 d
(3H, CH3, J 6.4 Hz), 1.50–1.64 m (3H, CH + CH2), 1.77–
1.86 m (2H, CH2), 3.05–3.17 m (2H, CH2), 3.65–3.55 m
(2H, CH2), 4.73 s (2H, CH2), 5.22 s (2H, CH2COOH),
7.27–7.36 m (2H, Ar), 7.56–7.61 m (1H, Ar), 8.15–
8.19 m (1H, Ar), 8.24 s (1H, C2H), 11.45 br.s (1H,
COOH). Mass spectrum: m/z 355 [M + 1]+. Found, %:
C 64.34; H 6.39; N 15.79. C19H22N4O3. Calculated, %:
C 64.39; H 6.26; N 15.81.
1
Yield 59%, mp 89–91°C. H NMR spectrum, δ, ppm:
1.35–1.65 m (17H), 1.74–1.84 m (2H, CH2), 2.46–
2.49 m (3H), 3.70–3.78 m (1H, CH), 3.82 s (2H, CH2),
4.92 s (2H, CH2CON), 7.24–7.33 m (2H, Ar), 7.44–
7.49 m (1H,Ar), 8.07–8.12 m (1H,Ar), 8.17 s (1H, C2H),
8.28 d (1H, NH, J 7.7 Hz). Mass spectrum: m/z 437 [M +
1]+. Found, %: C 69.03; H 7.73; N 16.09. C25H33N5O2.
Calculated, %: C 68.94; H 7.64; N 16.08.
N-(2-Furylmethyl)-(3-{5-[(4-methylpiperidin-1-
yl)methyl]-1,3,4-oxadiazol-2-yl}-1H-indol-1-yl)-
acetamide (VId). Yield 71%, mp 114–116°C. 1H NMR
spectrum, δ, ppm: 0.88 d (3H, CH3, J 6.4 Hz), 1.09–
1.24 m (2H, CH2), 1.25–1.37 m (1H, CH), 1.55–1.64 m
(2H, CH2), 2.07–2.19 m (2H, CH2), 2.82–2.92 m (2H,
CH2), 3.83 s (2H, CH2), 4.31 d (2H, NHCH2, J 6.0 Hz),
Amides VI. General procedure. To a solution of
2 mmol of acyd Va–Vd in 8 ml of DMSO was added
2.4 mmol of carbonyldiimidazole. The mixture was heated
to 50°C for 30 min, then to the solution was added 2.2
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ALYAB’EV et al.
724
5.02 c (2H, CH2CONH), 6.27 d (1H, C3Hfuran, J 3.0 Hz),
6.40 d.d (1H, C4Hfuran, J 1.8, J 3.0 Hz), 7.25–7.34 m (2H,
3. Danawade, D.S., Raghu, A.V., and Gadaginamath, G.S.,
Indian J. Chem. B, 2006, vol. 45, p. 689.
4. Ushakova, R.L., Mikaya,A.I., Zaikin, V.G., Kelarev, V.I., and
Shvekhgeimer, G.A., Khim. Geterotsikl. Soedin., 1986,
vol. 22, p. 539.
5. Kelarev, V.I. and Shvekhgeimer, G.A., Khim. Geterotsikl.
Soedin., 1982, p. 343.
6. Kelarev, V.I. and Shvekhgeimer, G.A., Izv. Vuzov, Ser. Khim.
i, Khim. Tekhnol., 1982, vol. 25, p. 1458.
7. Kelarev, V.I, Gasanov, S.Sh., Karakhanov, R.A., Poli-
vin, Yu.N., Kuatbekova, K.P., and Panina, M.E., Zh. Org.
Khim., 1992, vol. 28, p. 2561.
8. Farghaly, Abdel-Rahman, A.H., J. Chin. Chem. Soc., 2004,
vol. 51, p. 147.
Ar), 7.46–7.51 m (1H, Ar), 7.59 d (1H, C5Hfuran
,
J 1.8 Hz), 8.08–8.13 m (1H, Ar), 8.20 s (1H, C2H),
8.78 t (1H, NH, J 6.0 Hz). Mass spectrum: m/z 435 [M +
1]+. Found, %: C 66.57; H 6.33; N 16.19. C24H27N5O3.
Calculated, %: C 66.49; H 6.28; N 16.16.
REFERENCES
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 5 2009