Directed Aminomethylation of Pyrrole, Indole, and Carbazole with N,N,N′,N′-Tetramethylmethanediamine

Article abstract of DOI:10.1134/S1070428018050056

Catalytic aminomethylation of pyrrole and indole with N,N,N′,N′-tetramethylmethanediamine in the presence of 5 mol % of ZrOCl₂·8H₂O proceeds selectively at the positions 2, 5 of pyrrole and 1, 3 of indole. Carbazole under the same conditions affords 3-formyl-9-aminomethyl derivative. The reaction in the presence of 5 mol % of K₂CO₃ occurs as monoaminomethylation: for pyrrole at the position 2, for indole at the position 3, and for carbazole at the nitrogen atom of the substrate. Water-soluble 1,1′-(1H-pyrrole-2,5-diyl)bis(N,N-dimethylmethanamine) exhibits a fungistatic activity with respect to phytopathogenic fungi Rhizoctonia solani.

Full text of DOI:10.1134/S1070428018050056

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2018, Vol. 54, No. 5, pp. 701–706. © Pleiades Publishing, Ltd., 2018.
Original Russian Text © V.R. Akhmetova, E.M. Bikbulatova, N.S. Akhmadiev, V.M. Yanybin, T.F. Boiko, R.V. Kunakova, A.G. Ibragimov, 2018, published in
Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 5, pp. 699–704.
Directed Aminomethylation of Pyrrole, Indole, and Carbazole
with N,N,N′,N′-Tetramethylmethanediamine
V. R. Akhmetovaa, E. M. Bikbulatovaa, N. S. Akhmadieva, V. M. Yanybina,
T. F. Boikob, R. V. Kunakovac, and A. G. Ibragimova*
a Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075 Russia
*e-mail: vnirara@mail.ru
b Ufa Biological Institute, Russian Academy of Sciences, Ufa, 450054 Russia
c Ufa State Petroleum Technological University, Ufa, 450062 Russia
Received July 26, 2017
Abstract—Catalytic aminomethylation of pyrrole and indole with N,N,N′,N′-tetramethylmethanediamine in the
.
presence of 5 mol % of ZrOCl2 8H2O proceeds selectively at the positions 2, 5 of pyrrole and 1, 3 of indole.
Carbazole under the same conditions affords 3-formyl-9-aminomethyl derivative. The reaction in the presence
of 5 mol % of K2CO3 occurs as monoaminomethylation: for pyrrole at the position 2, for indole at the position
3, and for carbazole at the nitrogen atom of the substrate. Water-soluble 1,1'-(1H-pyrrole-2,5-diyl)bis(N,N-
dimethylmethanamine) exhibits a fungistatic activity with respect to phytopathogenic fungi Rhizoctonia solani.
DOI: 10.1134/S1070428018050056
Aminomethylation of aromatic CH-acids with
formaldehyde and secondary amines or with N,N,N′,N′
-tetramethylmethanediamine is used in the synthesis of
antifriction and antimicrobial additives, corrosion
inhibitors [1–3]. The aminomethylation of pyrrole
occurs in the positions 2 and N-, and of indole, in the
position 3 and N- at the promotion with excess SO2 or
with a system K2CO3–succinic anhydride [4, 5]. The
aminomethylation of pyrrole in the presence of
equimolar amount of activators Me3SiCl or MeSiCl3
proceeds with the formation of a mixture of 2- and 2,5-
aminomethyl derivatives [6].
Pearson concept [11]. The reaction was carried out
with excess of N,N,N′,N′-tetramethylmethanediamine 1
that acted as both a solvent and an efficient С-
electrophilic reagent.
The reaction of pyrrole with reagent 1 at 60°С
in the presence of “borderline” Lewis acids gives
a mixture of N- (2) and C- (3, 5) aminomethyl
derivatives whose content was measured by GC
and GC-MS methods (Scheme 1, Table 1, runs nos. 2,
3, 5).
The aminomethylation in the presence of
“soft” (PdCl2, CuCl/SiO2) or “hard” (AlCl3,
FeCl3·6H2O) acids, as well as in the presence of
We lately established that Lewis acids were
efficient catalysts of СН-activation of 1,3-dicarbonyl
compounds in thiomethylation [7–9]. Considering this
result we planned in this study to investigate the
catalytic activity of Lewis acids capable of activation
of C,N- and C,C-aminomethylation of pyrrole and its
benzo-fused systems, indole and carbazole, in reaction
with accessible N,N,N′,N′-tetramethylmethanediamine 1
[10].
K2CO3 base led to
a selective formation of
monoaminomethyl derivative 3 (Table 1, runs nos. 7,
9–11, 14), аnd in the presence of 5 mol % of
ZrOCl2·8H2O or HCl, of 2,5-bis(aminomethyl)
derivative 5 in a high yield (Table 1, runs nos. 12, 13).
The С-aminomethylation under the effect of 5 mol %
of CuCl and BuONa occurred nonselectively with the
formation of
a
mixture of 2- and 3-(dime-
We tested as catalysts “hard” (AlCl3, ZrOCl2·8H2O,
FeCl3·6H2O, Cp2TiCl2, HCl, K2CO3, BuONa), “bor-
derline” [Ni(acac)2, Sm(NO3)3·6H2O, CoCl2·6H2O],
and “soft” (CuCl, PdCl2) acids as estimated by
thylaminomethyl)pyrroles 3 and 4 in a ratio 1 : 1
(Table 1, runs nos. 8, 15). In acetonitrile in the
presence of 5 mol % of PdCl2 a mixture formed of
aminomethylpyrroles 2 and 3, 6 : 1. The reaction
701

AKHMETOVA et al.
702
Scheme 1.
PdCl2
+
N
CH3CN
N
N
H
3
N
2
N
60°C CuCl
N
N
3
+
+
or
N
BuONa
N
H
H
1
[M]
4
3
.
ZrOCl2 8H2O
N
N
N
H
5
[M] = PdCl2, CuCl/SiO2, AlCl3, FeCl3·6H2O, K2CO3.
without catalyst proceeded with the formation
of a mixture of products of N- and C-amino-
methylation 2–4 in an overall yield 30% (Table 1, run
no. 1).
The aminomethylation of indole with bisamine 1
similarly depends on the catalyst type. The reaction
takes two paths: С-aminomethylation gives N-(1Н-
indol-3-yl-methyl)-N,N-dimethylamine
6
in the
presence of K2CO3 at the indole conversion as low as
10% (Table 2, run no. 8). Yet in the presence of
Hence at heating pyrrole with N,N,N′,N′-tetra-
methylmethanediamine 1 the following reactions
proceed selectively: 2-aminomethylation in the
presence of Lewis acids (5 mol % CuCl/SiO2, PdCl2,
AlCl3 and FeCl3·6H2O or K2CO3), 2,5-diamino-
methylation in the presence of 5 mol % of
ZrOCl2·8H2O or HCl; prevailing N-aminomethylation
in acetonitrile in the presence of 5 mol % of PdCl2.
Scheme 2.
N
K2CO3
60°C
N
H
6
+
N
N
N
N
N
Table 1. Conditions of pyrrole aminomethylation, reaction
products ratio, and overall yield
H
.
ZrOCl2 8H2O
1
60°C
N
Run
no.
Catalyst,
5 mol %
Reaction products Overall yield,
ratio
%
7
1
2
3
–
2 : 3 : 4, 1 : 20 : 10
30
81
90
95
95
40
96
28
60
78
30
92
77
83
75
Table 2.Conditions of indole aminomethylation, reaction
products ratio, and overall yield
Sm(NO3)3 · 6H2O 2 : 3 : 5, 1 : 10 : 9
Ni(acac)2
Cp2TiCl2
CoCl2 · 6H2O
PdCl2
2 : 3 : 5, 2 : 1.5 : 1
Run.
No.
1
Reaction prod-
4
2 : 3, 1 : 1.2
2 : 3, 1 : 6
2 : 3, 6 : 1
Catalyst, 5 mol %
Overall yield, %
ucts ratio
5
6а
7
–
7
7
7
10
43
2
Sm(NO3)3·6H2O
Sm(NO3)3·6H2O
PdCl2
AlCl3
ZrOCl2·8H2O
PdCl2
CuCl
3
3а
4b
5
40
52
48
79
77
10
8
9
3 : 4, 1 : 1
CuCl/SiO2
AlCl3
FeCl3 · 6H2O
ZrOCl2 · 8H2O
HCl
3
3
3
5
5
3
7
10
11
12
13
14
15
6 : 7, 1 : 1
6
7
8
7
6 : 7, 1 : 5
6
HCl
K2CO3
K2CO3
BuONa
Solvents:
MeOH or
CH3CN.
а
3 : 4, 1 : 1
а
b
Solvent СН3СN.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 5 2018

DIRECTED AMINOMETHYLATION OF PYRROLE, INDOLE, AND CARBAZOLE
703
Scheme 3.
K2CO3
N
N
8
60°C
+
N
N
O
N
1
H
.
ZrOCl2 8H2O
8
+
N
N
9
Scheme 4.
H
.
O
ZrOCl2 8H2O
N
N
N
CH Zr(O)Cl
Cl
N
C
O
Cl
Zr(O)Cl
1
A
N
H
N
A
O
N
9
N
N
N
8
B
5 mol % of Sm(NO3)3·6H2O, PdCl2, ZrOCl2·8H2O
selectively formed 1,3-bis-(aminomethyl) derivative 7
in yields of 43, 52, and 79% respectively (Table 2,
runs nos. 2–4, 6). At the use of equimolar quantity of
K2CO3 amine 6 formed in the yield up to 70% [4]
(Scheme 2).
The carbazole reaction with bisamine 1 under the
chosen conditions occurred less effectively. We
succeeded to perform the N-aminomethylation in THF
in the presence of K2CO3 as a base with the formation
of N,N-dimethyl-9Н-carbazole-9-methanamine 8,
whose structure was reliably proved by X-ray
diffraction (XRD) (see the figure). The reaction in the
presence of 5 mol % of ZrOCl2·8H2O proceeded with
the formation of a mixture of amine 8 and 3-formyl
С7
С14
С11
С15
С5
С10
С13
С4
Table 3. Conditions of carbazole aminomethylation,
reaction products ratio, and overall yield
С9
N1
С3
С6
Run
no.
Catalyst,
5 mol %
Reaction
products ratio yield, %
Overall
С12
Solvent
С8
N2
1
2
K2CO3
THF
THF
C6H6–MeOH
1 : 1
8
32
50
С17
ZrOCl2·8H2O
8 : 9, 1.6 : 1
С16
3
4
ZrOCl·8H2O
ZrOCl2·8H2O
8 : 9, 1 : 1
8 : 9, 2 : 1
63
81
Molecular structure of N,N-dimethyl-9H-carbazole-9-
methanamine 8 according to XRD data.
CH3CN
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 5 2018

AKHMETOVA et al.
704
derivative 9, and their ratio depended on the solvent
nature (Table 3, runs nos. 2–4) (Scheme 3).
carrier gas helium. GC-MS analyses were performed
on a chromatograph Shimadzu GC 2010 with a
detector GCMS-QP2010 Ultra, capillary column
Supelco 5 ms (60 m × 0.25 mm × 0.25 µm), carrier gas
helium. Mass spectrum of compound 7 was recorded
on an instrument Bruker MALDI TOF Autoflex III. IR
spectra were taken on a spectrophotometer Bruker
Amine 8 was formerly prepared from carbazole and
reagent 1 in two stages through intermediate formation
of an organomagnesium derivative involving a
Grignard reagent [12], and the C-formylation of the N-
substituted carbazole occurred readily in the Duff
hexamine reaction yielding compounds possessing
antitumor activity [13].
1
Vertex-70V from mulls in mineral oil. Н and 13С
NMR spectra were registered on a spectrometer Bruker
Avance III HD 500 (500, 125 МHz) in CDCl3, internal
reference TMS, homo- and heteronuclear 2D
experiments were carried out using standard pulse
sequences of Bruker. Melting points were measured on
an apparatus РНМК 80/2617 (Kofler hot stage). The
reaction monitoring was done by TLC on Sorbfil
plates, eluent cyclohexane–СНСl3–EtOAc, 1 : 2 : 10,
development in iodine vapor.
It is presumable that the carbazole C-formylation
with the use of reagent 1 proceeds similarly to Duff
[14] or Vilsmeier-Haack reaction with the formation of
intermediate complex A and compound B (Scheme 4).
We presume that the carbazole formylation in the
position 3 occurs in polar solvents, e.g., THF, through
the formation of salt A related by the activity to
Vilsmeier-Haack reagent (chloroiminium salt).
Apparently the N-(aminomethyl) derivative 8 first
forms and under the action of chloroiminium salt A in
polar solvents converts into formyl derivative 9 via
intermediate B.
XRD analysis of the single crystal of compound 8
was performed on an automatic diffractometer
XСalibur Еos, equipped with a CCD-detector and a
source of MoKα-radiation (graphite monochromator, λ
0.71073 Å, ω-scanning, 2θmax°). Collection of data and
processing of results was performed using the program
Crys-AlisProOxford Diffraction Ltd. [16]. The structure
was solved by the direct method and refined using
SHELX program [17] in OLEX2 software [18] in full-
matrix least-squares method in anisotropic
approximation for nonhydrogen atoms. Hydrogen
atoms were localized from difference Fourier synthesis
and were included in the refinement with fixed
positions and thermal parameters.
Thus the catalyst ZrOCl2·8H2O is effective for the
directed С,С-aminomethylation of pyrrole, C,N-
aminomethylation of indole applying bisamine 1
without solvent, and also for С-formylation and N-
aminomethylation of carbazole in polar solvents.
Catalysis with 5 mol % of K2CO3 affords С-
monoaminomethylated derivatives of pyrrole and
indole, and with carbazole the reaction in THF
proceeds as N-aminomethylation.
Microscopic fungi used as test cultures were taken
from the collection of Ufa Biological Institute of the
Russian Academy of Sciences.
Among the synthesized compounds diamine 5 is water-
soluble. The evaluation of its biologic activity was per-
formed by diffusion in agar method [15], using as test
objects phytopathogenic fungi Fusarium oxysporum,
Bipolaris sorokiniana, and Rhizoctonia solani, which
are causing diseases of various agricultural plants.
Aminomethylation of pyrrole (indole, carbazole)
with reagent 1. General procedure. In a glass reactor
was charged 0.07 mL (1 mmol) of pyrrole (indole,
carbazole) and 0.66 mL (5 mmol) of bisamine 1. The
mixture was stirred at heating for 6 h in the presence of
5 mol % of the desired catalyst (Tables 1–3). On
cooling the mixture was passed through a bed of SiO2,
then evaporated on a rotary evaporator.
Compound 5 at the concentration of 0.5% showed a
fungistatic effect with respect to Rhizoctonia solani,
hampering its development and causing the formation
of untypical mycelium.
EXPERIMENTAL
N-(Dimethylaminomethyl)pyrrole (2). Yield
43%, resinous substance. IR spectrum, ν, cm–1: 3202,
3129, 3100, 2974, 2443, 1669, 1252, 1174, 1143,
1096, 1014, 843, 718, 611. 1Н NMR spectrum, δ, ppm:
2.23 s (6Н, СН3), 3.49 s (2Н, СH2), 5.28 m (2Нarom),
6.82 m (2Нarom). 13С NMR spectrum, δ, ppm: 44.36
(CH3), 71.10 (CH2), 110.97 (Сarom), 122.29 (Carom).
GC of reaction products was carried out on a
chromatograph Shimadzu GC-9A equipped with a
flame-ionization detector, steel column 2000 × 3 mm,
stationary phase SE-30 (5%) on carrier Chromoton N-
AW-HMDS, ramp 50–270°С, heating rate 8 deg/min,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 5 2018

DIRECTED AMINOMETHYLATION OF PYRROLE, INDOLE, AND CARBAZOLE
705
Mass spectrum, m/z (Irel, %): 124 (10) [M]+, 80 (20), 58
(10), 44 (100). M 124.10 [19].
2198, 1670, 1614, 1324, 1265, 1239, 1155, 1097,
1042, 909, 849, 805, 733, 643. Н NMR spectrum, δ,
1
ppm: 2.33 s (12Н, СН3), 3.68 s and 4.74 s (4Н, СH2),
7.14–7.75 m (5Н, Сarom). 13С NMR spectrum, δ, ppm:
42.73 and 45.32 (CH3), 54.49 and 68.65 (CH2), 110.00
(Сarom), 112.13 (Carom), 119.37 (Сarom), 119.45, 121.83,
128.11, 128.54, 137.28 (CNarom). Mass spectrum, m/z
(Irel, %): 230 [M – Н]. M 231.17 [20].
N,N-Dimethyl-1-(1Н-pyrrol-2-yl)methanamine
(3). Yield 96%, resinous substance. IR spectrum, ν, cm–1:
3377, 3100, 1669, 1252, 1174, 1143, 1096, 1014, 843,
1
718. Н NMR spectrum, δ, ppm: 2.26 s (6Н, СН3),
3.46 s (2Н, СH2), 6.11 s (1Нarom), 6.13 s (1Нarom), 6.73
s (1Нarom), 9.27 s (1Н, NH). 13С NMR spectrum, δ,
ppm: 44.96 (CH3), 56.63 (CH2), 107.12 (Сarom), 107.53
(Carom), 117.85 (СaromN), 129.02 (CaromN). Mass
spectrum, m/z (Irel, %): 124 (30) [M]+, 80 (100), 53
(15), 44 (25). M 124.10 [6].
1-(9Н-Carbazol-9-yl)-N,N-dimethylmethane-
amine (8). Yield 54%, colorless needle crystals. Rf
0.77, mp 67–68°С. Mass spectrum, m/z (Irel, %): 224
(10) [M]+, 58 (100), 42 (5) [12].
9-[(Dimethylamino)methyl]-9H-carbazole-3-
carbaldehyde (9). Yield 32%, yellow oily substance.
Rf 0.15, eluent cyclohexane–СНСl3–EtOAc, 1 : 2 : 10.
IR spectrum, ν, cm–1: 1768, 1599, 1239, 1037, 928,
858, 756, 574. 1Н NMR spectrum, δ, ppm: 2.50 s (6Н,
СН3), 3.93 s (2Н, СH2), 7.21–8.09 m (7Н, СНarom),
9.35 s (1Н, CH). 13С NMR spectrum, δ, ppm: 43.07
(CH3), 65.74 (CH2), 109.48 (Сarom), 110.78 (Сarom),
119.34 (Сarom), 120.08 (Сarom), 125.55 (Сarom), 125.76
(Сarom), 139.83 (CNarom), 162.74 (Сarom), 195.04 (СО).
Found, %: С 76.04; Н 6.56; N 11.19. С16Н16N2O.
Calculated, %: С 76.16; Н 6.39; N 11.10.
N,N-Dimethyl-1-(1Н-pyrrol-3-yl)methanamine
(4). Yield 38%, resinous substance. IR spectrum, ν, cm–1:
3376, 3205, 3128, 3115, 2970, 2443, 1662, 1252,
1
1174, 1143, 1096, 1014, 845, 731, 614. Н NMR
spectrum, δ, ppm: 2.22 s (6Н, СН3), 3.39 s (2Н, СH2),
5.28 s (1Нarom), 5.93 m (1Нarom), 6.82 m (1Нarom), 8.94
s (1Н, NH). 13С NMR spectrum, δ, ppm: 44.35 (CH3),
55.63 (CH2), 106.37 (Carom), 107.12 (Сarom), 117.85
(СaromN), 128.95 (CaromN). Mass spectrum, m/z (Irel,
%): 124 (15) [M]+, 80 (10), 58 (100), 42 (15). Found,
%: С 67.86; Н 9.64; N 22.48. С7Н12N2. Calculated, %:
С 67.70; Н 9.74; N 22.56. M 124.10.
Crystallographic parameters and details of
refinement of the crystal structure of amine 8.
C15H16N2. M 224.30. Crystal lattice orthorhombic,
space group 19: P212121. Unit cell parameters: a
5.2971(10), b 13.249(2), c 17.886(3) Å, α = β = γ =
90°, V 1255.3(3) Å3, Z 5; T 293(2) K, μ(MoKα)
0.088 mm–1, dcalc 1.484 g/cm3. 2380 independent
reflections were observed (Rint 0286) in the range of
indices –3≤h≤7, –18≤k≤ 16, –24≤l≤ 22. The final
values of convergence factors are as follows: R1
0.0483 for 2380 independent reflections with I>2σ(I),
wR2 0.0905 for all independent reflections. Complete
XRD data are deposited in Cambridge Crystallo-
graphic Data Centre (CCDC 1551084).
1,1'-(1H-Pyrrole-2,5-diyl)bis(N,N-dimethylme-
thanamine) (5). Yield 92%, resinous substance. IR
spectrum, ν, cm–1: 3459, 3140, 1661, 1252, 1174,
1
1142, 1097, 1041, 845, 767. Н NMR spectrum, δ,
ppm: 2.20 s (12Н, СН3), 3.37 s (4Н, СH2), 5.92 s
(2Нarom), 9.04 s (1Н, NH). 13С NMR spectrum, δ, ppm:
44.99 (CH3), 56.67 (CH2), 107.08 (Сarom), 128.97
(CaromN). Mass spectrum, m/z (Irel, %): 181 (15) [M]+,
137 (55) 93 (100) 80 (10), 58 (85), 42 (20). M 181.16
[6].
N-(1Н-Indol-3-ylmethyl)-N,N-dimethylamine (6).
Yield 24%, resinous substance. IR spectrum, ν, cm–1:
3408, 3049, 1676, 1614, 1557, 1513, 1237, 1180,
1
1154, 1098, 1016, 849, 806, 723, 626, 570, 426. Н
NMR spectrum, δ, ppm: 2.26 s (6Н, СН3), 3.56 s (2Н,
СH2), 6.91 s (1Нarom), 7.08, 7.12, 7.53, 7.70 m (4Н,
С
(CH2), 111.12 (Сarom), 112.27 (Carom), 119.5 (СaromN),
120.2 (Carom), 123.90, 127.80, 136.30. Mass spectrum,
m/z (Irel, %): 174 (5) [M]+, 130 (5), 58 (100), 42 (5). M
174.12 [4].
ACKNOWLEDGMENTS
arom). 13С NMR spectrum, δ, ppm: 45.16 (CH3), 53.93
The study was performed under the partial financial
support of the Russian Foundation for Basic Research
and Academy of Sciences of Bashkortostan Republic
(projects nos. 17-43-020292 р_а and 4.6007.2017/8.9)
and within the framework of the State contract (АААА-
А17-117012610060-7).
1,1'-(1H-Indole-1,3-diyl)bis(N,N-dimethyl-
methanamine) (7). Yield 79%, resinous substance. IR
spectrum, ν, cm–1: 3467, 3051, 2973, 2941, 2244,
The authors are grateful to the researcher from the
laboratory of structural chemistry E.S. Meshcheryakova
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 5 2018

AKHMETOVA et al.
706
9. Akhmetova, V.R., Akhmadiev, N.S., Starikova, Z.A.,
Tulyabaev, A.R., Mescheryakova, E.S., and Ibragi-
mov, A.G., Tetrahedron, 2015, vol. 71, p. 7722.
for performing XRD analysis. The structural investiga-
tion of compounds obtained was carried out on equip-
ment of the Regional Center of joint usage “Agidel.”
10. Levashova, V.I. and Nikonorova, N.I., Korroziya, Mat.,
Zashchita, 2008, p. 37.
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