Single-Pot Synthesis of Alkyl-Substituted Quinolines and Indoles via Photoinduced Oxidation of Primary Alcohols

Article abstract of DOI:10.1134/S1070363218050080

Single-pot synthesis of alkyl-substituted quinolines and indoles has been performed via photoinduced oxidation of primary aliphatic alcohols (C₂–C₅) and condensation of the aldehydes (products of the alcohols oxidation) with aniline under the action of iron-containing catalysts and inorganic oxidants. The synthesis was the most efficient in the presence of FeCl₃·6H₂O as catalyst and 10% aqueous solution of NaOCl as oxidant with irradiation by Hg lamp. The synthesis mechanism through photoinduced oxidation of primary aliphatic alcohol has been suggested.

Full text of DOI:10.1134/S1070363218050080

ISSN 1070-3632, Russian Journal of General Chemistry, 2018, Vol. 88, No. 5, pp. 892–897. © Pleiades Publishing, Ltd., 2018.
Original Russian Text © A.R. Makhmutov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 5, pp. 747–753.
Single-Pot Synthesis of Alkyl-Substituted Quinolines
and Indoles via Photoinduced Oxidation of Primary Alcohols
A. R. Makhmutova*
a Bashkir State University, ul. Z. Validi 32, Ufa, 450076 Russia
*e-mail: ainurmax@mail.ru
Received December 28, 2017
Abstract—Single-pot synthesis of alkyl-substituted quinolines and indoles has been performed via
photoinduced oxidation of primary aliphatic alcohols (С2–С5) and condensation of the aldehydes (products of
the alcohols oxidation) with aniline under the action of iron-containing catalysts and inorganic oxidants. The
synthesis was the most efficient in the presence of FeCl3·6H2O as catalyst and 10% aqueous solution of NaOCl
as oxidant with irradiation by Hg lamp. The synthesis mechanism through photoinduced oxidation of primary
aliphatic alcohol has been suggested.
Keywords: alkylquinolines, alkylindoles, aliphatic alcohols, hypochlorites, photoinduced oxidation
DOI: 10.1134/S1070363218050080
The approaches based on activation with UV or
visible light as alternative to heat-induced (thermal)
reactions have become important methods of catalytic
synthesis of organic compounds [1–5]. This peculiar
method has been used in the synthesis of nitrogen-
containing heterocyclic compounds. For example,
regioselective synthesis of indole derivatives induced
by visible light has been described [6]. The reaction
between arylamines, terminal alkyne, and quinones
occurs in the presence of copper(I) chloride as catalyst.
The reaction of o-ethenylaryl isocyanides with organic
disulfides [(PhTe)2 catalyst] photoinduced by visible
light leads to sulfur-containing indole derivatives [7].
Photoinduced synthesis of quinoline bases from
diazonium tetrafluoroborate and alkenes or alkynes in
the presence of NaBH4 in acetonitrile with different
photocatalysts has been studied [8]. The highest
efficiency was observed in the case of 10-methyl-9,10-
dihydroacridine catalyst.
from quinolines can be used in the synthesis of nano-
and mesostructured compounds, interesting materials
for organic electronics and nonlinear optics [17].
Several thermal methods of synthesis of derivatives
of indoles [18] and quinolines [19–21] have been
described, yet the photocatalytic and photoinduced
synthesis of these nitrogen-containing heterocycles are
advantageous since they use simpler and better
available reactants. At the same time, this process has
been scarcely studied so far. Herein, we present the
data on the single-pot synthesis of alkyl-substituted
quinolines and indoles via photoinduced oxidation of
primary aliphatic alcohols and dark catalytic
condensation of the formed aldehydes with aniline
under the action of iron-containing catalysts and
inorganic oxidants.
Modeling of single-pot synthesis of alkyl-sub-
stituted quinolines and indoles. The single-pot syn-
thesis of alkyl-substituted quinolines and indoles was
studied in ethanol using a model system shown in
Scheme 1. The conditions optimization was targeted at
the choice of the most efficient catalyst and oxidizer
and investigation of the photoactivation effect. In the
model system, the products (2-methyl-1,2-dihydro-
quinoline 2a, 2-methylquinoline 2b, and 2,3-
dimethylindol 2c) were formed in the 1 : 1 : 1 molar
ratio. In contrast to the known catalytic condensation
It is known that indole and quinoline derivatives are
found in various alkaloids, many of which exhibit high
biological activity. In view of this, derivatives of
indole and quinoline have been widely applied in the
synthesis of novel drugs [9–14]. Moreover, quinolines
and tetrahydroquinolines are ligand of chiral catalysts
[15] and are used in the production of organic light-
emitting diodes (OLED) [16]. Polyquinolines prepared
892

SINGLE-POT SYNTHESIS OF ALKYL-SUBSTITUTED QUINOLINES
893
Scheme 1.
cat (4 mol %) hν
EtOH (400 mmol)
oxidant (100 mmol)
H2O, 20°C, 4 h
N
NH2
1 (50 mmol)
N
H
2b
2а
+
N
H
2c
of aniline with aliphatic aldehyde [22], N-alkylanilines
were not formed. The studied model system was
elaborated basing on the two-stage catalytic synthesis
of 2,3-dialkylquinolines via condensation of the
products of alcohols photooxidation with aniline in the
presence of FeCl3·6H2O [23].
condensation of acetaldehyde with aniline occurred in
the same reactor but without irradiation. The highest
efficiency of the stage of EtOH oxidation and, hence,
the overall process, was observed under irradiation
with Hg lamp (Table 1, Exp. 1), whereas irradiation
with Xe lamp was less efficient (Table 1, Exp. 2).
However, acceptable result could be achieved with
prolonged (24 h) irradiation with visible light. Without
any photoactivation (in the dark chamber), the stage of
EtOH was very slow, and the resulting conversion of
compound 1 during 4 h was as low as 5% (Table 1,
Exp. 3).
The effects of the nature of catalyst and oxidation
as well as photoactivation on the conversion of starting
aniline 1 (used as the merit of the overall process
efficiency) are summarized in Table 1. The following
catalysts were tested: FeCl3·6H2O, Fe2(SO4)3·9H2O,
Fe(NO3)3·6H2O, K3[Fe(CN)6], Fe(acac)3, and Fe(OAc)2.
The highest catalytic efficiency was observed for
FeCl3·6H2O (Table 1, Exp. 1). Fe2(SO4)3·9H2O, Fe
(NO3)3·6H2O, and Fe(OAc)2 were somewhat less
active (Table 1, Exp. 4–6). The K3[Fe(CN)6] and
Fe(acac)3 complexes did not reveal catalytic activity
(Table 1, Exp. 7, 8).
Thermal activation (up to 100°С) of EtOH
oxidation with aqueous solution of NaOCl catalyzed
by FeCl3·6H2O led to poor selectivity of the alcohol
oxidation, yielding a mixture of acetaldehyde, acetic
acid, acetal, ethyl acetate, and the chlorination
products, similarly to the known haloform reaction
[30]. Hence, the selectivity of the alcohol oxidation
was reduced on heating, and further condensation stage
will become nonselective as well.
Known selective oxidants transforming alcohols
into the corresponding aldehydes: DMSO, CrO3, and
K2Cr2O7 [24], I2 [25], NaOCl, KOCl, and Ca(OCl)2
[26–29] were also tested in the model system. DMSO
did not reveal the oxidation activity (Table 1, Exp. 11).
K2Cr2O7 (Exp. 12) and CrO3 (Exp. 13) were converted
into the chromite Fe(CrO2)2 in an aqueous-alcoholic
solution of iron(III) chloride. The iodoform reaction
occurred in the experiment with I2 (Table 1, Exp. 14).
Possible mechanism of synthesis of alkyl-
substituted quinolines and indoles via photoinduced
oxidation of primary aliphatic alcohols in the model
system. UV irradiation is known to improve the
efficiency of the Fenton process, due to the generation
·
of hydroxyl radicals: Fe(H2O)3+ + hν → Fe2+ + OH +
H+ [31, 32]. The maximum in the absorption spectrum
(λmax) of the hydrate complex Fe(H2O)3+ is at 240 nm.
Hence, photoactivation with a medium-pressure Hg
lamp (spectral range 222–1368 nm) could produce the
·OH radicals in the model system. The photogenerated
·OH could induce the radical oxidation of alcohols into
aldehydes under a Hg lamp irradiation in the
FeCl3·6H2O–ROH system [33]. Basing on that, we
suggested the following mechanism of synthesis of
compounds 2a–2c in the model system (Scheme 2).
Only aqueous solutions of hypochlorites NaOCl
(Table 1, Exp. 1–6) and KOCl (Exp. 9) with mass
fraction of the active compound 10% revealed
acceptable oxidation activity. Aqueous suspension of
Ca(OCl)2 was less active (Table 1, Exp. 10).
Photoactivation of the model active was selective.
It was targeted exclusively on the acceleration of the
oxidation of ethanol into acetaldehyde with aqueous
solution of NaOCl catalyzed by FeCl3·6H2O. Further
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 5 2018

894
MAKHMUTOV
Table 1. Effect of the catalyst and oxidant nature and photoactivation on conversion of aniline in model reaction
Exp.
no.
Conversion, Exp.
Conversion,
%
Catalyst
Oxidant Photoactivation
Catalyst
Oxidant Photoactivation
%
no.
1
2
3
4
5
6
7
FeCl3·6H2O
NaOCl
UV
(λ<400 nm)
>99
8
Fe(acac)3
NaOCl
UV
(λ<400 nm)
–
FeCl3·6H2O
FeCl3·6H2O
NaOCl Visible light
33
5
9
FeCl3·6H2O KOCl
UV
(λ<400 nm)
91
84
–
(λ>400 nm)
NaOCl Dark chamber
10 FeCl3·6H2O Ca(OCl)2
11 FeCl3·6H2O DMSO
12 FeCl3·6H2O K2Cr2O7
13 FeCl3·6H2O CrO3
14 FeCl3·6H2O I2
UV
(λ<400 nm)
Fe2(SO4)3·9H2O NaOCl
Fe(NO3)3·6H2O NaOCl
UV
(λ<400 nm)
95
98
72
–
UV
(λ<400 nm)
UV
(λ<400 nm)
UV
(λ<400 nm)
27
34
Fe(OAc)2
NaOCl
NaOCl
UV
(λ<400 nm)
UV
(λ<400 nm)
K3[Fe(CN)6]
UV
(λ<400 nm)
UV
(λ<400 nm)
Iodoform
reaction
Fe(H2O)3+ ions absorbed quants of a Hg lamp irradia-
tion and oxidized the coordinated water molecules
with the formation of hydroxyl radicals and hyd-
roxonium ions. Reduced Fe2+ ions were converted
back into the hydrated Fe(H2O)3+ ions under the action
of the oxidizer hypochlorite in acidic medium. Hence,
a cyclic photoredox process generating hydroxyl radical
was induced in the system. The alcohol molecules
were oxidized by the hydroxyl radicals in an aqueous
medium into acetaldehyde. Acetaldehyde was accu-
mulated in the system only at the photoactivation stage.
the nature of the primary alcohol (С2–С5) on the
conversion of aniline 1 and the products composition
(Table 2). Synthesis of alkyl-substituted quinolines and
indoles in shown in Scheme 3.
The reaction products contained substituted
hydroquinolines 2a–5a, quinolines 2b–5b, and 2,3-
dialkylindoles 2c–5c. The yield of quinolines 2b–5b
was somewhat increased with the increase in the length
of the hydrocarbon part of the alcohol, but the con-
version of aniline was down to 87% (Table 2, Exp. 4).
In summary, we developed a single-pot method of
synthesis of alkyl-substituted quinolines and indoles,
via photoinduced oxidation of primary alcohol С2–С5
with a Hg lamp irradiation, followed by condensation
of the formed aldehydes with anilines in dark with
FeCl3·6H2O as catalyst and 10% aqueous solution of
NaOCl as oxidant. The synthesis occurs at room
temperature and atmospheric pressure in an aqueous
medium within 4 h. The mechanism of the process was
suggested.
The second stage of the single-pot synthesis, catalytic
condensation, occurred upon addition of aniline
without irradiation. The condensation led to the formation
of the Schiff’s bases (azomethines) in two forms:
aldimine 2A and enamine 2B. Fe3+ ions induced the
intermolecular cyclization of the azomethines 2A, 2B
(pathway a) into 1,2-dihydroquinoline 2a. That process
was accompanied by elimination of aniline [34, 35].
Product 2b was formed via oxidation of compound 2a
with NaOCl.
EXPERIMENTAL
The formation of 2,3-dimethylindole 2c from
azomethine likely occurred via the pathway b under
the catalytic action of Fe2+ ions, since the product 2c
appeared only in the deficiency of the oxidant in the
system (no more than 100 mmol of hypochlorite),
when Fe2+ were relatively stable.
The starting chemicals (“chemical pure” grade,
EKOS-1, Russia): ethanol, propanol-1, butanol-1,
pentanol-1, diethyl ether, and aniline were purified by
distillation [36]. The catalysts: FeCl3·6H2O, Fe2(SO4)3·
9H2O, Fe(NO3)3·6H2O (“pure” grade, Brom, Russia),
Fe(acac)3, Fe(OAc)2 (Acros Organics), K3[Fe(CN)6]
(“pure” grade, Reakhim, Russia) were used as
Effect of the alcohol nature on the synthesis of alkyl-
substituted quinolines and indoles. Slight influence of
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 5 2018

SINGLE-POT SYNTHESIS OF ALKYL-SUBSTITUTED QUINOLINES
895
Scheme 2.
hν
2Fe(H2O)3+
EtOH
NaCl
NaOCl
2b
N
CH3
CH2
_2H2O
_H2O
_NaCl
2а
2 OH
a
2A
[Fe3+ + Fe2+
_1
]
O
2Fe2+ + 2H+
NaOCl
1
_H2O
b
H3C
H
H2O
2c
N
H
2B
Scheme 3.
R
R
.
FeCl3 6H2O (4 mol %) hν
RCH2CH2OH (400 mmol)
NaOCl (100 mmol)
H2O, 20°C, 4 h
N
CH2R
NH2
N
CH2R
H
2b_5b
2а_5a
1 (50 mmol)
+
CH2R
CH2R
N
H
2c_5c
R = H, CH3, C2H5, C3H7.
received. Aqueous solutions of hypochlorites NaOCl
and KOCl (10 wt%) were prepared from chlorinated
lime (A grade, Vekton, Russia) as described elsewhere
[37].
1H and 13C NMR spectra were recorded on equip-
ment at the Center for the Сollective Use “Chemistry”
of the Institute of Organic Chemistry at the Ufa
Scientific Centre of the Russian Academy of Sciences:
Bruker Avance III spectrometer operating at 500.13
(1H) and 125.47 MHz (13C) with TMS as internal reference.
The products were identified using a GCMS-
QP2010S Ultra SHIMADZU chromato–mass spectro-
meter (column Restek Rtx-5MS, 30 m × 0.25 mm ID,
0.25 µm). Quantitative analysis of the products was
performed using a hardware-software complex based
on Khromatek-Kristall 5000.1 and 5000.2 chromato-
graphs (columns Agilent Technologies 19091F-413
HP-FFAP, 30 m × 0.32 mm, 0.25 Micron; Analytical
Science 30 m × 0.32 mm ID-BPS, 0.5 µm).
Single-pot synthesis of alkyl-substituted quinolines
and indoles via photoinduced oxidation of primary
aliphatic alcohols (general procedure). The synthesis
was performed using a Photo Catalytic Reactor Lelesil
Innovative Systems photocatalytic setup with a
250 mL photoreactor equipped with a magnetic stirrer.
74.5 mL of 10 wt% aqueous solution of NaOCl
Table 2. Effect of alcohol nature on conversion of aniline and composition of products of single-pot synthesis of alkyl-
substituted quinolines and indoles
Exp. no.
Alcohol
Ethanol
Conversion, %
Products composition, %
2b (37)
1
2
3
4
>99
92
2a (31)
3a (32)
4a (32)
5a (34)
2c (32)
3c (30)
4c (29)
5c (25)
Propanol-1
Butanol-1
Propanol-1
3b (38)
89
4b (39)
87
5b (41)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 5 2018

896
MAKHMUTOV
(100 mmol) were added at continuous stirring to a
mixture of 2.0 mmol (4 mol% with respect to aniline)
of a catalyst and 400 mmol of the corresponding
alcohol. A 250 W medium-pressure Hg lamp was used
as the irradiation source (spectral composition: 48%
UV, 43% visible, 9% IR, 222–1368 nm). The light flux
reached the reaction mixture after passing through an
aqueous layer at 20°C, irradiation time 4 h. After the
irradiation, 4.6 mL (50 mmol) of aniline was added to
the mixture; it was stirred during 5 min and extracted
with diethyl ether. The organic layer was separated and
dried over anhydrous magnesium sulfate. Diethyl ether
was distilled off, and the residue was analyzed and
distilled under reduced pressure. Physico-chemical
parameters of the reaction products coincided with the
reference data [18–21].
129.22 (С3), 133.93 (С4), 146.41 (С8a), 162.11 (С2).
Mass spectrum, m/z: 199 [M]+.
2-Butyl-3-propylquinoline (5b). Yield 41%,
1
yellow oil, bp 143°C (1 mmHg). H NMR spectrum
(CDCl3), δ, ppm: 1.13 t [3H, (CH2)2CH2CH3, J =
7.2 Hz], 1.25 t (3H, CH2CH2CH3, J = 7.2 Hz), 1.38 m
[2H, (CH2)2CH2CH3], 1.71 m (2H, CH2CH2CH3), 1.75
m (2H, CH2CH2CH2CH3), 2.72 t [2H, CH2(CH2)2CH3,
J = 7.5 Hz], 2.81 t (2H, CH2CH2CH3, J = 7.2 Hz), 7.53
t (1H, С6H, J = 7.8 Hz), 7.62 t (1H, С7H, J = 7.8 Hz),
7.65 s (1H, С4H), 7.78 d (1H, С5H, J = 7.8 Hz), 8.01 d
(1H, С8H, J = 7.9 Hz). 13С NMR spectrum, δС, ppm:
13.42 [(CH2)2CH2CH3], 13.99 (CH2CH2CH3), 22.81
[(CH2)2CH2CH3],
23.26
(CH2CH2CH3),
31.92
(CH2CH2CH2CH3), 34.43 [CH2(CH2)2CH3], 35.76
(CH2CH2CH3), 125.55 (С7), 126.92 (С5), 127.29 (С6),
128.36 (С8), 128.54 (С4a), 130.21 (С3), 134.23 (С4),
146.85 (С8a), 161.17 (С2). Mass spectrum, m/z: 227 [M]+.
2-Methylquinoline (2b). Yield 37%, yellow oil, bp
1
80–81°C (2 mmHg). H NMR spectrum (CDCl3), δ,
ppm: 2.78 s (3H, CH3), 7.22 d (1H, C3H, J = 8.0 Hz),
7.46 t (1H, C6H, J = 7.5 Hz), 7.68 t (1H, C7H, J =
7.5 Hz), 7.73 d (1H, C5H, J = 9.2 Hz), 7.97 d (1H,
C8H, J = 8.0 Hz), 8.03 d (1H, C4H, J = 7.5 Hz). 13С
NMR spectrum, δС, ppm: 25.12 (CH3), 121.74 (С3),
125.45 (С6), 126.32 (С4a), 127.37 (С5), 128.80 (С8),
129.19 (С7), 135.84 (С4), 147.76 (С8a), 158.67 (С2).
Mass spectrum, m/z: 143 [M]+.
2,3-Dimethylindole (2c). Yield 32%, white crystals,
mp 98–100°C. H NMR spectrum (CDCl3), δ, ppm:
1
2.21 s (3H, CH3), 2.31 s (3H, CH3), 6.95–7.05 m (2H,
С5H, С6H), 7.19 d (2H, С7H, J = 7.9 Hz), 7.48 d (2H,
С4H, J = 8.0 Hz), 7.66 br.s (1Н, NH). 13С NMR spectrum,
δС, ppm: 8.43 (CH3), 11.55 (CH3), 107.35 (С3), 110.28
(С7), 117.83 (С4), 118.87 (С5), 120.77 (С6), 129.39
(С3a), 130.64 (С2), 135.18 (С7a). Mass spectrum, m/z:
145 [M]+.
2-Ethyl-3-methylquinoline (3b). Yield 38%, yellow
oil, bp 97–99°C (2 mmHg). 1H NMR spectrum
(CDCl3), δ, ppm: 1.38 t (3H, CH2CH3, J = 7.2 Hz),
2.38 s (3Н, CH3), 2.96 q (2Н, CH2, J = 7.6 Hz), 7.40 t
(1H, C7H, J = 8.0 Hz), 7.58 t (1H, C6H, J = 8.0 Hz),
7.62 d (1H, C5H, J = 8.0 Hz), 7.70 s (1H, C4H), 8.06 d
(1H, C8H, J = 8.0 Hz). 13С NMR spectrum, δС, ppm:
12.84 (CH2CH3), 18.61 (CH3), 29.44 (CH2CH3),
125.61 (С7), 126.72 (С6), 127.38 (С5), 128.23 (С4a),
128.51 (С8), 129.37 (С3), 135.64 (С4), 146.76 (С8a),
163.21 (С2). Mass spectrum, m/z: 171 [M]+.
2,3-Diethylindole (3c). Yield 30%, colorless crystals,
1
mp 29–30°C. H NMR spectrum (CDCl3), δ, ppm:
1.16 t (3H, CH3, J = 7.4 Hz), 1.17 t (3H, CH3, J =
7.4 Hz), 2.76 q (2Н, CH2, J = 7.4 Hz), 3.03 q (2Н,
CH2, J = 7.4 Hz), 7.01–7.05 m (2H, С5H, С6H), 7.11 d
(2H, С7H, J = 7.9 Hz), 7.51 d (2H, С4H, J = 8.0 Hz),
7.69 br.s (1Н, NH). 13С NMR spectrum, δС, ppm: 13.39
(CH3), 13.69 (CH3), 21.84 (CH2), 22.21 (CH2), 110.83
(С3), 111.36 (С7), 117.88 (С4), 120.20 (С5), 122.27 (С6),
127.62 (С3a), 136.33 (С7a), 141.59 (С2). Mass spectrum,
m/z: 173 [M]+.
2-Propyl-3-ethylquinoline (4b). Yield 39%, yellow
1
oil, bp 118°C (1 mmHg). H NMR spectrum (CDCl3),
2,3-Dipropylindole (4c). Yield 29%, pale yellow
1
δ, ppm: 0.97 t (3H, CH2CH2CH3, J = 7.2 Hz), 1.11 t
(3H, CH2CH3, J = 7.2 Hz), 1.80–1.90 m (2H,
CH2CH2CH3), 2.82 q (2Н, СH2CH3, J = 7.2 Hz), 2.99 t
(2Н, CH2CH2CH3, J = 8.0 Hz), 7.44 t (1H, С7H, J =
8.0 Hz), 7.62 t (1H, С6H, J = 7.2 Hz), 7.72 d (1H, С5H,
J = 7.6 Hz), 7.84 s (1H, С4H), 8.08 d (1H, С8H, J =
8.0 Hz). 13С NMR spectrum, δС, ppm: 14.41
(CH2CH2CH3), 14.53 (CH2CH3), 22.96 (CH2CH2CH3),
25.23 (СH2CH3), 37.85 (CH2CH2CH3), 125.68 (С7),
126.96 (С5), 127.08 (С6), 127.55 (С4a), 128.41 (С8),
oil, bp 144°C (1 mmHg). H NMR spectrum (CDCl3),
δ, ppm: 0.95 t (3H, CH3, J = 6.5 Hz), 0.98 t (3H, CH3,
J = 6.6 Hz), 1.71–1.73 m (4H, CH2CH2CH3), 2.73–
2.92 m (4H, CH2CH2CH3), 6.96–7.05 m (2H, С5H,
С6H), 7.21 d (2H, С7H, J = 7.9 Hz), 7.49 d (2H, С4H,
J = 8.0 Hz), 7.61 br.s (1Н, NH). 13С NMR spectrum,
δС, ppm: 13.35 (CH3), 13.48 (CH3), 22.08
(CH2CH2CH3),
22.30
(CH2CH2CH3),
25.58
(CH2CH2CH3), 30.05 (CH2CH2CH3), 111.02 (С3),
111.26 (С7), 118.47 (С4), 120.24 (С5), 122.33 (С6),
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 5 2018

SINGLE-POT SYNTHESIS OF ALKYL-SUBSTITUTED QUINOLINES
897
128.05 (С3a), 135.68 (С7a), 137.16 (С2). Mass spectrum,
m/z: 201 [M]+.
17. Makhmutov, A.R., Mustafin, A.G., and Usmanov, S.M.,
Int. J. Environ. Sci. Educ., 2016, vol. 11, p. 11831.
18. Tursky, M., Lorentz-Petersen, L.L.R., Olsen, L.B., and
Madsen, R., Org. Biomol. Chem., 2010, vol. 8, p. 5576.
doi 10.1039/c0ob00106f
2,3-Dibutylindole (5c). Yield 25%, pale yellow oil,
1
bp 162°C (1 mmHg). H NMR spectrum (CDCl3), δ,
ppm: 0.88 t (3H, CH3, J = 6.5 Hz), 0.92 t (3H, CH3,
J = 6.5 Hz), 1.36–1.42 m [4H, (CH2)2CH2CH3], 1.62–
1.67 m (4H, CH2CH2CH2CH3), 2.75–2.94 m [4H,
CH2(CH2)2CH3], 6.96–7.08 m (2H, С5H, С6H), 7.26 d
(2H, С7H, J = 8.0 Hz), 7.52 d (2H, С4H, J = 8.0 Hz),
7.68 br.s (1Н, NH). 13С NMR spectrum, δС, ppm:
13.76 (CH3), 13.82 (CH3), 22.06 [(CH2)2CH2CH3], 22.38
[(CH2)2CH2CH3], 30.54 (CH2CH2CH2CH3), 33.03
(CH2CH2CH2CH3), 24.36 [CH2(CH2)2CH3], 27.94
[CH2(CH2)2CH3], 109.12 (С3), 111.01 (С7), 117.09
(С4), 119.58 (С5), 121.79 (С6), 127.83 (С3a), 136.02
(С7a), 136.75 (С2). Mass spectrum, m/z: 229 [M]+.
19. Khusnutdinov, R.I., Bayguzina, A.R., and Aminov, R.I.,
Russ. Chem. Bull., 2013, vol. 62, p. 133. doi 10.1007/
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 5 2018