Russian Journal of Organic Chemistry, Vol. 40, No. 7, 2004, pp. 982–985. Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 7, 2004,
pp. 1023–1026.
Original Russian Text Copyright © 2004 by Kolyamshin, Danilov.
N-Aryl-2-dialkylaminosuccinimides
O. A. Kolyamshin and V. A. Danilov
Ul’yanov Chuvash State University, Moskovskii pr. 15, Cheboksary, 428015 Russia
Received December 2, 2003
Abstract—Reaction of N-arylmaleimides with an equimolar amount of diethylamine, piperidine, and
morpholine afforded the corresponding N-aryl-2-dialkylaminosuccinimides as mixtures of stereoisomers.
1
3440 cm–1. The H NMR spectra of the products
Some N-aryl-2-(4-alkyl-1-piperazinyl)- and N-aryl-
2-(2-benzimidazolyl)succinimides were found to
exhibit somnific, anticonvulsant, antiarrythmic, and
other kinds of biological activity [1–3]. On the other
hand, the number of known compounds of this series is
relatively small. Therefore, synthesis of new 2-amino-
substituted N-arylsuccinimides is important. Taking
into account the above stated, we have synthesized
new N-aryl-2-dialkylaminosuccinimides and exaimed
their properties. The syntheses were performed by
heating mixtures of equimolar amounts of N-aryl-
maleimides Ia–Il and diethylamine (IIa), piperidine
(IIb), or morpholine (IIc) in dioxane at 45–100°C
(Scheme 1).
(except for IIIa, IIId, IVa, IVd, Va, and Vd) con-
tained signals from protons of the endocyclic CH2
group as a doublet of doublets at δ 2.58–2.87 ppm
(3JHH = 4, 12 Hz) and a quartet at δ 2.87–3.03 ppm
(3JHH = 8 Hz). The 2-H proton in IIIb and IIIe–IIIi
appeared as a quartet at δ 4.13–4.30 ppm, and the
corresponding signal of compounds IVb, IVc, IVg,
IVi, Vb, Vc, and Vg was located at δ 3.94–4.06 ppm
(q, 3JHH = 4 Hz). The presence of a methyl group in the
ortho position of the aromatic ring in compounds IIId,
IVd, and Vd leads to additional splitting of the CH2
and CH signals, and the latter appear as octets in
the corresponding spectral region, the above given
coupling constants remaining unchanged. The ob-
served pattern indicates that these compounds are
mixtures of stereoisomers.
Succinimides IIIa–IIIi and IVa–IVj (Table 1) are
crystalline or amorphous powders with different colors
(from colorless to bright orange). Their purity was
checked by TLC, and the structure was confirmed by
1
elemental analysis and IR and H NMR spectroscopy
EXPERIMENTAL
(Table 2). In the IR spectra of succinimides III and IV,
stretching vibrations of the carbonyl groups give rise to
one or two strong bands in the region 1710–1655 cm–1
and a medium-intensity band 1775–1730 cm–1; also,
a weak but characteristic overtone is observed at 3470–
The IR spectra were recorded on a Specord IR-75
spectrometer, and the H NMR spectra were obtained
on a Bruker DRX-500 instrument (500.13 MHz) in
DMSO-d6 using TMS as internal reference. TLC
1
Scheme 1.
'
NR2
'
+
R2NH
O
O
O
O
N
N
C6H4R
C6H4R
IIIa–IIIi, IVa–IVj, Va–Vg
Ia–Il
IIa–IIc
I, R = o-NO2 (a), m-NO2 (b), p-NO2 (c), o-Me (d), m-Me (e), p-Me (f), p-PhN=N (g), o-piperidino (h), p-piperidino (i), o-BuO (j),
p-BuO (k), m-PhCONH (l); II, R' = Et (a), R' = (CH2)5 (b), R2' = (CH2)2O(CH2)2 (c); III, R' = Et, R = o-NO2 (a), m-NO2 (b),
2
p-NO2 (c), o-Me (d), m-Me (e), p-Me (f), p-PhN=N (g), p-piperidino (h), m-PhCONH (i); IV, R' =(CH2)5, R = o-NO2 (a),
2
m-NO2 (b), p-NO2 (c), o-Me (d), m-Me (e), p-Me (f), p-PhN=N (g), p-piperidino (g), o-BuO (i), p-BuO (j); V, R'2 = (CH2)2O(CH2)2,
R = o-NO2 (a), m-NO2 (b), p-NO2 (c), o-Me (d), m-Me (e),p-Me (f), p-PhN=N (g).
1070-4280/04/4007-0982 © 2004 MAIK “Nauka/Interperiodica”
Kolyamshin
