Synthesis of indole 2,3-epoxypropyl derivatives and their reactions with amines

Article abstract of DOI:10.1007/s11178-005-0149-3

Indole derivatives with a 2,3-epoxypropyl substituent attached to nitrogen were synthesized. In reactions with primary and secondary amines these compounds afforded the corresponding 1,2-aminoalcohols. 2005 Pleiades Publishing, Inc.

Full text of DOI:10.1007/s11178-005-0149-3

Russian Journal of Organic Chemistry, Vol. 41, No. 2, 2005, pp. 233-237. Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005,
pp. 243-246.
Original Russian Text Copyright Ó 2005 by Suzdalev, Babakova.
Synthesis of Indole 2,3-Epoxypropyl Derivatives
and Their Reactions with Amines
K.F. Suzdalev and M.N. Babakova
Research Institute of Physical and Organic Chemistry, Rostov State University, Rostov-on-Don, 344090 Russia
Received August 10, 2003
Abstract—Indole derivatives with a 2,3-epoxypropyl substituent attached to nitrogen were synthesized. In
reactions with primary and secondary amines these compounds afforded the corresponding 1,2-aminoalcohols.
apparently occurred as N-alkylation. To accelerate the
process we used epibromohydrin instead of epichloro-
hydrin (Scheme 1). The initial 5-methyl-4-[(1H-indol-3-
yl)methylene]-2-phenyl-2,4-dihydropyrazol-3-one (I) was
obtained from indole-3-carbaldehyde and the correspond-
ing pyrazolone by Knoevenagel condensation.
2,3-Epoxypropyl derivatives of various heterocycles
are interesting objects for preparation of pharmaco-
logically active 1,2-aminoalcohols [1, 2]. Besides the
epoxides of the heterocyclic series proper are known to
exhibit antitumor activity [3]. Inasmuch as the indole ring
is present in numerous pharmaceuticals and alkaloids we
studied the possibility to synthesize N-epoxypropyl deriva-
tives of indole. Moreover, the indole containing in position
3 a 1,2-aminoalcohol moiety is known to by administered
in the therapy of heart diseases [4].
Alongside compound II product III formed also in
a low yield by reaction of one epibromohydrin mole-
cule with two molecules of compound I. Compound III
formation occurred presumably through the opening of
the epoxy ring in compound II by indole I N-anion.
A similar compound was isolated from the products of
reaction between carbazole derivatives and epichloro-
hydrin [6].
The goal of this study was preparation of indole
N-epoxypropyl derivatives and investigation of their
reactions with amines.
Reactions of highly basic azoles with epichlorohydrin
in the presence of alkali were described in [5], and the
reaction mechanism was discussed. It was suggested that
the process might start as a direct interaction of the
reagents not involving the alkali. This reaction path is
impossible for indole derivatives of low basicity, therefore
we first have generated the N-indolyl anion by treatment
with sodium hydride in DMSO. The subsequent reaction
Epoxy derivatives Va, Vb were obtained under similar
conditions from indole-containing chalcones IVa, IVb
and epibromohydrine (Scheme 2).
In this case no compound like III was obtained.
Reactions of epoxides II and Va, Vb with amines
were investigated. Despite the presence in the initial
reagents of reactive keto groups and double bonds the
Scheme 1.
2
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,,
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1070-4280/05/4102-0233Ó2005 Pleiades Publishing, Inc.

234
SUZDALEV, BABAKOVA
Scheme 2.
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2
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IV, V, R = Me (a), OMe (b).
Scheme 3.
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errors. The yields are given with respect to the quantity
of recrystallized substances.
amines attack the epoxy ring affording 1,2-aminoalcohols
VIa–VIe and VIIa–VIIc (Scheme 3).
The structure of compounds obtained was confirmed
by spectral data.
Initial indole chalchones IVa, IVb were obtained by
procedure [7].
Thus we developed a synthetic method for 3-
substituted indoles containing a 1,2-aminoalcohol moiety
at the indole nitrogen atom.
5-Methyl-4-[(1H-indol-3-yl)methylene]-2-
phenyl-2,4-dihydropyrazol-3-one (I). A mixture of
1.45 g (0.01 mol) of indole-3-carbaldehyde, 1.74 g
(0.01 mol) of 3-methyl-1-phenyl-2-pyrazolin-5-one, and
0.17 g (23 mol%) of piperidine was heated at reflux in
10 ml of butanol for 1 h. On cooling the precipitate was
filtered off. Yield 2.72 g (90%), bright orange crystals,
EXPERIMENTAL
1H NMR spectra were registered on a spectrometer
Varian Unity-300 (300 MHz), IR spectra were recorded
on Specord 75IR instrument from mulls in mineral oil.
The elemental analyses (C, H, N) of compounds
synthesized (I, II, III, Va, Vb, VIa–VIe, VIIa–VIIc)
correspond to those calculated within the limits of common
–1
mp 138–140°C. IR spectrum, n, cm : 1587–1607 (C=C,
1
C–Carom), 1653 (C=O), 3223 (NH). H NMR spectrum
(CDCl3), d, ppm: 2.45 s (3H, CH3), 7.20–8.09 m (10H,
H
arom), 10.10 d (1H, CH=), 10.27 br.s (1H, NH). Found,
RUSSIAN JOURNALOF ORGANIC CHEMISTRY Vol. 41 No. 2 2005

SYNTHESIS OF INDOLE 2,3-EPOXYPROPYL DERIVATIVES
235
%: C 75.9; H 4.9; N 14.1. M 301. C19H15N3O.
Calculated, %: C 75.7; H 5.0; N 14.0. M 301.36.
CH=). Found, %: C 77.3; H 5.3; N 12.3. M 341.
C22H19N3O. Calculated, %: C 77.4; H 5.6; N 12.3.
M 341.4.
5-Methyl-4-{[1-(2,3-epoxyprop-1-yl)-1H-indol-3-
yl]methylene}-2-phenyl-2,4-dihydropyrazol-3-one
(II) and 1,3-di[3-(5-oxo-3-methyl-1-phenyl-1,5-
dihydropyrazol-4-ylidenemethyl)indole-1-yl]propan-
2-ol (III). To 0.75 g (0.019 mol) of 60% suspension of
sodium hydride in mineral oil mixed with 10 ml of
anhydrous DMSO was added at stirring 5 g (0.017 mol)
of compound I. As soon as the hydrogen evolution
stopped (approximately in 30 min) 4.98 g (0.036 mol) of
epibromohydrin and 2 ml of DMSO was added. The
mixture was stirred for 3 h at room temperature, the
separated precipitate of compound III was filtered off
and washed with 2-propanol. Yield 0.25 g (4%) , orange
1-(4-Methylphenyl)-3-[1-(2,3-epoxyprop-1-yl)-
1H-indol-3-yl]prop-2-en-1-one (Va). To 0.24 g
(6 mmol) of 60% suspension of sodium hydride in mineral
oil mixed with 5 ml of anhydrous DMSO was added at
stirring 1.32 g (5 mmol) of chalcone IVa (product of indole-
3-carbaldehyde reaction with acetophenone). In 30 min,
when the hydrogen evolution finished, 2.08 g (15 mmol)
of epibromohydrine was added. Within 1 h the solvent
changed color from dark red to dark yellow. The mixture
was left overnight, an then 0.5 ml of water was added
dropwise. The separated precipitate was filtered off,
washed with methanol, recrystallized ftom 7 ml of
2-propanol. Yield 0.88 g (55%), lemon-yellow needle
crystals, mp 121–122°C (i-PrOH). IR spectrum, n,
–1
powder, mp 280°C (from DMF). IR spectrum, n, cm :
1
1600 (C–Carom), 1660, 1673 (C=O), 3366 (OH). H NMR
spectrum (DMSO-d6), d, ppm: 2.40 s (6H, 2CH3), 4.30–
4.40 m (3H, CH2, CH), 4.83 d (2H, CH2), 5.62 d (1H,
OH), 7.10–8.22 m (20H, Harom), 9.90 s (2H, 2–CH=).
Found, %: C 74.5; H 5.3; N 12.7. M 659. C41H34N6O3.
Calculated, %: C 74.7; H 5.2; N 12.8. M 658.9.
–1
cm : 1590, 1607 (C–Carom, C=C), 1646 (C=O). 1H NMR
spectrum (CDCl3), d, ppm: 2.40 s (3H, CH3), 2.47–
2.53 m, 2.80–2.90 m (1H, 1H, OCH2), 3.08–3.15 m (1H,
CH), 4.18 d.d, 4.52 d.d (1H, 1H, NCH2), 7.15–8.10 m
(11H, Harom, CH=CH). Found, %: C 79.7; H 6.1; N 4.2.
M 340. C21H19NO2. Calculated, %: C 79.5; H 6.0;
N 4.4. M 340.2.
The mother liquor in DMSO left after the first filtration
was diluted with water and extracted with chloroform
(3´30 ml). The extract was twice washed with water,
dried over anhydrous Na2SO4, and the solvent was
distilled off. To the residue 5–7 ml of butanol was added,
and crystallization was provoked by grinding. The
separated precipitate of red-orange color was filtered off,
washed with petroleum ether (bp 40–70°C), and
recrystallized from butanol. Yield of compound II 3.82 g
1-(4-Methoxyphenyl)-3-[1-(2,3-epoxyprop-1-yl)-
1H-indol-3-yl]prop-2-en-1-one (Vb) was obtained like
epoxide Va from chalcone IVb. Yield 61%, lemon-yellow
–1
needle crystals, mp 125–126°C. IR spectrum, n, cm :
1587, 1603 (C–Carom, C=C), 1640 (C=O). 1H NMR
spectrum (CDCl3), d, ppm: 2.43–2.53 m, 2.80–2.88 m
(1H, 1H, OCH2), 3.27–3.35 m (1H, CH), 3.90 s (3H,
OCH3), 4.17 d.d, 4.52 d.d (1H, 1H, NCH2), 6.90–8.13 m
(11H, Harom, CH=CH).
–1
(63%), mp 163°C. IR spectrum, n, cm : 1607 (C=C,
1
C–Carom), 1667 (C=O). H NMR spectrum (CDCl3), d,
ppm: 2.42 s (3H, CH3), 2.52–2.62 m, 2.82–2.92 m (1H,
1H, OCH2), 3.30–3.40 m (1H, CH), 4.30 d.d, 4.60 d.d
(1H, 1H, NCH2), 7.15–8.00 (10H, Harom), 9.90 s (1H,
4-{[1-(3-Amino-2-hydroxypropyl)-1H-indol-3-
yl]methylene}-5-methyl-2-phenyl-2,4-dihydro-
Table 1. Reaction conditions for preparation of 1,2-aminoalcohols
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RUSSIAN JOURNALOF ORGANIC CHEMISTRY Vol. 41 No. 2 2005

236
SUZDALEV, BABAKOVA
Table 2. Spectral characteristics of 1,2-aminoalcohols
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9,,Dꢀ ꢂꢀꢂꢄ±ꢂꢀꢋꢄꢀPꢀꢆꢋ+ꢁꢀ&+ 1&+ ꢈꢁꢀꢂꢀꢋꢂꢀVꢀꢆꢃ+ꢁꢀ&+ ꢈꢁꢀꢂꢀꢅꢃ±ꢂꢀꢉꢌꢀPꢀꢆꢂ+ꢁꢀ&+ 1
ꢈꢁꢀꢃꢀꢋꢌꢀEUꢀVꢀꢊꢅꢌꢄꢁꢀꢊꢅꢍꢄꢀꢆ& &ꢈꢁꢀ
ꢈꢁꢀꢇꢀꢂꢄ±ꢌꢀꢊꢅꢀPꢀꢊꢉꢋꢄꢀꢆ& 2ꢈꢁꢀꢃꢃꢍꢅꢀ
ꢆ2+ꢈꢀ
ꢀ
ꢆꢊ+ꢁꢀ2+ꢈꢁꢀꢃꢀꢉꢄ±ꢃꢀꢇꢅꢀPꢀꢆꢋ+ꢁꢀ&+ 2&+ ꢈꢁꢀꢋꢀꢄꢃ±ꢋꢀꢃꢃꢀPꢀꢆꢃ+ꢁꢀ&+ꢁꢀ&+ 1
ꢆꢊꢊ+ꢁꢀ+ ꢁꢀ±&+ &+±ꢈꢀ
ꢀ
9,,Eꢀ ꢂꢀꢂꢄ±ꢂꢀꢋꢃꢀPꢀꢆꢋ+ꢁ&+ 1&+ ꢈꢁꢀꢂꢀꢅꢂ±ꢂꢀꢉꢍꢀPꢀꢆꢂ+ꢁꢀ&+ 1
ꢈꢁꢀꢃꢀꢋꢌꢀEUꢀVꢀꢆꢊ+ꢁꢀ2+ꢈꢁꢀꢃꢀꢅꢍ±ꢃꢀꢇꢌꢀꢊꢅꢌꢄꢁꢀꢊꢉꢄꢄꢀꢆ& &ꢈꢁꢀ
ꢈꢁꢀ ꢇꢀꢂꢄ±ꢌꢀꢊꢂꢀ Pꢀꢊꢉꢋꢄꢀꢆ& 2ꢈꢁꢀꢃꢃꢍꢃꢀ
ꢆꢊꢊ+ꢁꢀ+ ꢁꢀ±&+ &+±ꢈꢀꢂꢀꢂꢂꢀVꢀꢆꢃ+ꢁꢀ&+ ꢈꢁꢀꢂꢀꢅꢂꢀEUꢀVꢀꢆꢊ+ꢁꢀ1+ꢈꢁꢀꢃꢀꢊꢂꢀGꢀGꢁꢀꢃꢀꢃꢂꢀGꢀGꢀꢆꢊ+ꢁꢀꢊ+ꢁꢀꢆ2+ꢈꢀ
ꢀ
ꢀ
Pꢀ ꢆꢋ+ꢁꢀ &+ 2&+ ꢈꢁꢀ ꢃꢀꢌꢌꢀ Vꢀ ꢆꢃ+ꢁꢀ 2&+ ꢈꢁꢀ ꢋꢀꢄꢅ±ꢋꢀꢃꢅꢀ Pꢀ ꢆꢃ+ꢁꢀ &+ꢁꢀ &+ 1
9,,Fꢀ &+ 1
ꢈꢁꢀ ꢃꢀꢇꢄ±ꢃꢀꢍꢄꢀ EUꢀVꢀ ꢆꢊ+ꢁꢀ 2+ꢈꢁꢀ ꢃꢀꢌꢇꢀ Vꢀ ꢆꢃ+ꢁꢀ 2&+ ꢈꢁꢀ ꢋꢀꢊꢅ±ꢋꢀꢋꢄꢀ Pꢀ ꢆꢃ+ꢁꢀ &+ 1
ꢁꢀꢊꢅꢍꢉꢁꢀꢊꢉꢄꢄꢀꢆ& &ꢈꢁꢀ
ꢊꢉꢃꢉꢀꢆ& 2ꢈꢁꢀꢃꢃꢋꢄꢀ
ꢆ1+ꢁꢀ2+ꢈꢀ
&+ꢈꢁꢀꢉꢀꢅꢊ±ꢌꢀꢊꢄꢀPꢀꢆꢊꢅ+ꢁꢀ+ ꢁꢀ±&+ &+±ꢈꢀ
ꢀ
Table 3. Elemental analyses of 1,2-aminoalcohols
)RXQGꢁꢀ"ꢀꢀ
&DOFXODWHGꢁꢀ"ꢀ
+ꢀ
&RPSGꢀꢀQRꢀꢀ
)RUPXODꢀꢀ
&ꢀ
+ꢀ
1ꢀ
&ꢀ
1ꢀ
9,Dꢀ
9,Eꢀ
9,Fꢀ
9,Gꢀ
9,Hꢀ
9,,Dꢀ
9,,Eꢀ
9,,Fꢀ
ꢇꢄꢀꢋꢀ
ꢇꢄꢀꢇꢀ
ꢇꢋꢀꢊꢀ
ꢇꢋꢀꢂꢀ
ꢉꢍꢀꢊꢀ
ꢇꢋꢀꢊꢀ
ꢇꢊꢀꢋꢀ
ꢇꢅꢀꢉꢀ
ꢉꢀꢋꢀ
ꢉꢀꢌꢀ
ꢇꢀꢌꢀ
ꢇꢀꢌꢀ
ꢉꢀꢍꢀ
ꢇꢀꢊꢀ
ꢉꢀꢍꢀ
ꢉꢀꢋꢀ
ꢊꢂꢀꢋꢀ
ꢊꢅꢀꢊꢀ
ꢊꢊꢀꢋꢀ
ꢊꢊꢀꢋꢀ
ꢊꢋꢀꢂꢀ
ꢉꢀꢍꢀ
& + 1 2 ꢀ
& + 1 2 ꢀ
& + 1 2 ꢀ
& + 1 2 ꢀ
& + 1 2 ꢀ
& + 1 2 ꢀ
& + 1 2 ꢀ
& + 1 2 ꢀ
ꢇꢄꢀꢃꢀ
ꢇꢄꢀꢍꢀ
ꢇꢋꢀꢄꢀ
ꢇꢋꢀꢄꢀ
ꢉꢍꢀꢄꢀ
ꢇꢋꢀꢂꢀ
ꢇꢊꢀꢋꢀ
ꢇꢅꢀꢇꢀ
ꢉꢀꢃꢀ
ꢉꢀꢌ±ꢇꢀꢍꢀ
ꢇꢀꢍꢀ
ꢇꢀꢍꢀ
ꢉꢀꢌꢀ
ꢇꢀꢄꢀ
ꢉꢀꢇꢀ
ꢉꢀꢅꢀ
ꢊꢂꢀꢉꢀ
ꢊꢅꢀꢃꢀ
ꢊꢊꢀꢅꢀ
ꢊꢊꢀꢅꢀ
ꢊꢋꢀꢋꢀ
ꢉꢀꢍꢀ
ꢉꢀꢅꢀ
ꢉꢀꢇꢀ
ꢉꢀꢇꢀ
ꢉꢀꢅꢀ
ꢀ
pyrazol-3-ones (VIa–VIe) and 3-[1-(3-amino-2-
hydroxypropyl)-1H-indol-3yl]-1-phenylprop-2-en-1-
ones (VIIa–VIIc). Compounds III and Va, Vb were
boiled with amines in toluene. The reaction conditions
are given in Table 1. An individual procedure was
developed for isolation of every compound. Compounds
VIa, VId, VIe precipitated from the reaction mixture on
cooling. Compounds VIb and VIIa–VIIc were
precipitated by adding petroleum ether (bp. 40–70°C) to
the cooled reaction mixture. Compound VIc was isolated
after distilling off the solvent by adding 2-propanol to the
residue. Spectral characteristics of compounds are given
in Table 2, and elemental analyses, in Table 3.
REFERENCES
1. Gella, I.M., Azotistye geterotsikly i alkaloidy (Nitrogen-
containing Heterocycles and Alkaloids), Kartsev, V.G. and
Tolstikov, G.A., Moscow: Iridium-Press, 2001, vol. 2, p. 81.
2. Malawska, B., Kulig, K., Filipek, B., Sapa, J., Maciag, D.,
Zygmunt, M., and Antkiewicz-Michaluk, L., Eur. J. Med.
RUSSIAN JOURNALOF ORGANIC CHEMISTRY Vol. 41 No. 2 2005

SYNTHESIS OF INDOLE 2,3-EPOXYPROPYL DERIVATIVES
vol. 32, p. 1076.
237
Chem., 2002, vol. 37, p. 183.
6. Rovkina, N.M., Zherebtsov, I.P., Lopatinskii, V.P., and Baty-
rova, L.M., Gella, I.M., Azotistye geterotsikly i alkaloidy
(Nitrogen-containing Heterocycles andAlkaloids), Kartsev,
V.G. and Tolstikov, G.A., Moscow: Iridium-Press, 2001, vol. 2,
p. 251.
7. Zhungietu, G.I., Budylin, V.A., and Kost, A.N., Prepara-
tivnaya khimiya indola (Preparative Chemistry of Indole),
Kishinev: ShTIINTsA, 1975, p. 197.
3. Korotkikh, I.I., Losev, G.A., and Shvaika, O.P., Azotistye
geterotsikly i alkaloidy (Nitrogen-containing Heterocycles
and Alkaloids), Kartsev, V.G. and Tolstikov, G.A., Ed.,
Moscow: Iridium-Press, 2001, vol. 1, p. 350.
4. Kreighbaum, W.E., Matier, L., Dennis, R.D., Minielli, J.L.,
Deitch-man, D., Perhach, J.L., and Comer, W.T.Jr., J. Med.
Chem., 1980, vol. 23, p. 285.
5. Korotkikh, I.I. and Shvaika, O.P., Zh. Org. Khim., 1996,
RUSSIAN JOURNALOF ORGANIC CHEMISTRY Vol. 41 No. 2 2005