Endic acid diamides. Synthesis and reactivity

Article abstract of DOI:10.1134/S107042800707007X

A number of symmetric and unsymmetric endo-cis-dicarboxamides of the norbornene series containing dimethyl- and diethylamine, morpholine, perhydroazepine, and p-bromoaniline fragments were synthesized starting from endic anhydride with the aid of N,N′-dic

Full text of DOI:10.1134/S107042800707007X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2007, Vol. 43, No. 7, pp. 984–989. © Pleiades Publishing, Ltd., 2007.
Original Russian Text © V.A. Pal’chikov, I.N. Tarabara, L.I. Kas’yan, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 7, pp. 990–995.
Endic Acid Diamides. Synthesis and Reactivity
V. A. Pal’chikov, I. N. Tarabara, and L. I. Kas’yan
Dnepropetrovsk National University, per. Nauchnyi 13, Dnepropetrovsk, 49625 Ukraine
e-mail: cf@ff.dsu.dp.ua
Received September 5, 2006
Abstract—A number of symmetric and unsymmetric endo-cis-dicarboxamides of the norbornene series
containing dimethyl- and diethylamine, morpholine, perhydroazepine, and p-bromoaniline fragments were
synthesized starting from endic anhydride with the aid of N,N′-dicyclohexylcarbodiimide. Oxidation of these
3,7
amides with organic peroxy acids according to Prilezhaev gave exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0 ]-
1
nonane-endo-9-carboxylic acid salts. The structure of the obtained products was confirmed by IR and H NMR
spectroscopy.
DOI: 10.1134/S107042800707007X
Development of methods of synthesis of dicarbox-
imides derived from commercially available bicyclo-
N-Alkylamides of cyclic dicarboxylic acids are
used in medicine due to their ability to exert general
restorative effect on the central nervous system.
Among these, the most widely known are Neospiran,
Vandid, Anacardiol, and Endomid (IIIc) [13, 14].
Metabolism of the latter was studied in detail in [14].
Many trans-diamides of the bicyclo[2.2.1]hept-2-ene
and bicyclo[2.2.2]oct-2-ene series, as well as their
saturated analogs, were synthesized by aminolysis of
cyclopenta- and cyclohexadiene adducts with fumaroyl
chloride [13, 15–17]. Some diamides were obtained
by Diels–Alder reactions involving fumaric acid di-
amides. However, no systematic studies on the reac-
tivity and physiological activity of these compounds
were performed.
Taking into account that all attempts to obtain bicy-
clo[2.2.1]hept-5-ene-endo,endo-2,3-dicarbonyl dichlo-
ride were unsuccessful [treatment of endic acid (II)
with classical chlorinating agents leads to the forma-
tion of only anhydride I], in the present work we
developed procedures for the preparation of some
symmetric and unsymmetric endo-cis-diamides of the
norbornene series from endic acid (II) and its mono-
amides usig N,N′-dicyclohexylcarbodiimide (DCC) as
condensing agent. In such a way, from monoamide
IV we synthesized diamides Va–Vc in high yield
[
2.2.1]hept-5-ene-endo,endo-2,3-dicarboxylic anhy-
dride (I, endic anhydride) and their reactivity were the
subjects of numerous publications [1–5]. However,
endic acid monoamides (amido acids) and diamides
have been studied to a considerably lesser extent [5–9].
Gallo and Gellman [10] performed an IR study on
NH···π hydrogen bonding in norbornenedicarbox-
amides having a secondary amide group. Some recent
publications [11, 12] were concerned with the syn-
thesis and conformational behavior of norbornene-con-
taining acyclic and cyclic peptides IIIa and IIIb.
R R'
O
O
O
O
N
H
O
NH
OMe
OMe
R
O
R'
O
I
IIIa
O
O
Pep
NEt2
(
Scheme 1). Unsymmetrical diamide Vd was obtained
O
Pep
from monoamides VI and VII which (like amido acid
IV) were prepared by aminolysis of anhydride I. On
the other hand, symmetric diamides VIIIa and VIIIb
were synthesized in high yields from both acid II and
the corresponding monoamides VI and VII (Scheme 2).
O
NEt2
T
IIIb
IIIc
R, R′ = Alk; T = cystine/adamantane/norbornene.
984

ENDIC ACID DIAMIDES. SYNTHESIS AND REACTIVITY
985
Scheme 1.
1
.3 M Me NH in CH Cl , DCC
2 2 2
CONMe2
94%
CONMe2
Va
Me NH, PhH, 25°C
Et NH, DCC, CH Cl
2 2 2
2
I
COOH
CONEt2
84%
CONMe2
CONMe2
IV
Vb
Morpholine, DCC, CH Cl2
2
C(O)N(CH CH ) O
90%
2
2 2
CONMe2
Vc
Following an analogous procedure, we synthesized
symmetric diamide VIIIc (yield 78%) including two
perhydroazepine fragments. The above reactions gen-
erally take 2–7 days (TLC data), and the yields of the
target products range from 51 to 94%. The scope of the
proposed procedure is limited: we failed to obtain di-
amide VIIId having a secondary amide group from
amido acid IX; instead, we isolated previously report-
ed [18] imide X in 77% yield. When amide VII was
used as initial compound, 42% of diamide VIIId was
obtained (Scheme 3).
reaction of equimolar amounts of anhydride I and
p-bromoaniline in benzene at room temperature. The
structure of all newly synthesized compounds was con-
1
firmed by the IR and H NMR spectra. In the IR spec-
tra of diamides Va–Vd and VIIIa–VIIId, the carbonyl
–1
stretching vibration band appeared at 1670–1630 cm
(
amide I). Compound VIIId displayed additional ab-
–1
sorption bands at 1540 (δN–H, amide II) and 1278 cm
(
νC–N, amide III) due to the secondary amide group
[
3
21], as well as N–H stretching vibration band at
280 cm . Stretching and bending vibrations of the
–
1
Compounds IV, VI, and VII were described by us
previously [19, 20]. Amide IX was synthesized by
norbornene =C–H bond appeared at 3075–3020 and
735–715 cm , respectively [21, 22].
–
1
Scheme 2.
Et NH, DCC, CH Cl
2Et NH, 2DCC, CH Cl
2 2 2
2
2
2
8
6%
90%
COOH
CONEt2
CONEt2
COOH
COOH
II
CONEt2
VI
VIIIa
NH
NH
2
7
7%
94%
O
O
DCC, CH Cl2
2DCC, CH Cl
2
2
2
Et NH, DCC, CH Cl
Morpholine, DCC, CH Cl2
2
2
2
2
O
O
O
N
5
1%
87%
N
O
N
O
O
CONEt2
COOH
O
N
O
Vd
VII
VIIIb
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 7 2007

9
86
PAL’CHIKOV et al.
Scheme 3.
Morpholine
CH Cl2
2
O
DCC, CH Cl
2
2
O
CONHC H Br-4
CONHC H Br-4 H N
77%
6
4
6
4
2
COO–
NC H Br-4
6 4
COOH
O
IX
X
O
4-BrC H NH , DCC, CH Cl
2
6
4
2
2
O
N
N
O
O
4
2%
COOH
O
NHC
VIIId
6
H
4
Br-4
VII
1
The H NMR spectra of diamides Va–Vd and
VIIIa–VIIId contained signals in the δ region 5.73–
.23 ppm from the olefinic 5-H and 6-H protons; the
situ at 0 and 25°C, respectively, gave the correspond-
ing ammonium exo-2-hydroxy-5-oxo-4-oxatricyclo-
3
,7
6
[4.2.1.0 ]nonane-endo-9-carboxylates XI–XIII as the
only products (Scheme 4). In the reaction of peroxy-
acetic acid with trans-diamide IIIc, lactone XIV was
isolated instead of the expected salt [14] (Scheme 5).
We tried to synthesize amidolactone XV by oxidation
of diamide VIIIb under milder conditions, using a so-
lution of monoperoxyphthalic acid generated in situ in
ethyl acetate at room temperature; however, only 80%
of the initial compound was recovered from the reac-
tion mixture.
latter are nonequivalent in molecules of unsymmetrical
diamides Vb–Vd and VIIId (∆δ = 0.13–0.50 ppm).
Signals from protons in the bridgehead positions (1-H
and 4-H) were located at δ 2.93–3.12 ppm, and 2-H
and 3-H resonated at δ 3.31–3.51 ppm. Protons in the
methylene bridge (syn-7-H and anti-7-H) had fairly
similar chemical shifts (δ 1.18–1.38 ppm), and their
signals were split with a geminal coupling constant
2
J of 7.4–8.1 Hz. In the spectrum of amide VIIId we
also observed a downfield singlet at δ 9.73 ppm, be-
longing to the NH proton.
Salts XI–XIII were synthesized by us previously
19, 20] by epoxidation of amido acids obtained from
[
We also examined oxidation of diamides VIIIa–
VIIIc according to Prilezhaev. Treatment of these
compounds with peroxyformic or peroxyacetic acid in
endic anhydride (I). Scheme 6 illustrates a probable re-
action mechanism. Nucleophilic attack by the oxygen
atom of the carboxamide group on the nearest electro-
Scheme 4.
R'CO H (2 equiv)
HO
3
R'COOH
–
CONR2
CONR2
COO H NR
2 2
O
O
VIIIa–VIIIc
XI–XIII
VIIIa, XI, R = Et; VIIIb, XII, R
2
N = morpholino; VIIIc, XIII, R
2
N = perhydroazepin-1-yl; R′ = H, Me.
Scheme 5.
H+
O
O
O
O
HO
HO
NEt2
MeCO
H
3
NEt2
NEt2
–
Et NH
2
N
O
O
O
O
O
·
·
O
NEt2
O
NEt2
–OH
O
IIIc
XIV
XV
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 7 2007

ENDIC ACID DIAMIDES. SYNTHESIS AND REACTIVITY
987
Scheme 6.
H
O
HO
HO
R'CO H
H O
2
3
VIIIa–VIIIc
–
CONR2
NR2
CONR2
COO H NR
2 2
–
R NH
2
O
O
O
NR2
XVII
O
XVI
XI–XIII
philic carbon atom in protonated epoxy derivative XVI
gives intermediate XVII which undergoes hydrolysis
at the imino and amide groups to produce ammonium
salts XI–XIII.
a solution of N,N′-dicyclohexylcarbodiimide in a small
amount of methylene chloride was added. The mixture
was stirred at room temperature until the reaction was
complete (TLC), and the precipitate of N,N′-dicyclo-
hexylurea was filtered off, washed on a filter with
anhydrous methylene chloride, and dried, The filtrate
was evaporated under reduced pressure, the residue
was ground with diethyl ether (to remove residual
DCC), and the product was filtered off, washed, dried,
and recrystallized from propan-2-ol or acetone.
EXPERIMENTAL
The IR spectra were recorded in KBr on UR-20 and
Perkin–Elmer Paragon 500 FT-IR spectrometers. The
1
H NMR spectra were measured on Varian VXR spec-
trometers at 200 and 300 MHz from solutions in
N,N,N′,N′-Tetramethylbicyclo[2.2.1]hept-5-ene-
endo,endo-2,3-dicarboxamide (Va). Yield 4.44 g
DMSO-d using tetramethylsilane as internal refer-
6
ence. The progress of reactions and the purity of prod-
ucts were monitored by TLC on Silufol UV-254 plates
using diethyl ether (A) or propan-2-ol (B) as eluent;
spots were visualized by treatment with iodine vapor.
The elemental compositions were determined on
a Carlo Erba analyzer.
(
94%), mp 132–134°C, R 0.27 (B). IR spectrum, ν,
f
–
1
cm : 3025, 1635, 1475, 1415, 1270, 1160, 715.
1
H NMR spectrum (300 MHz), δ, ppm: 5.98 m (2H,
5
4
-H, 6-H), 3.47 m (2H, 2-H, 3-H), 2.98 m (2H, 1-H,
-H), 2.89 s (6H, CH ), 2.67 s (6H, CH ), 1.36 d (1H,
3
3
2
syn-7-H), 1.20 d (1H, anti-7-H, J = 8.1 Hz). Found,
endo-3-(p-Bromophenylcarbamoyl)bicyclo[2.2.1]-
hept-5-ene-endo-2-carboxylic acid (IX). p-Bromo-
aniline, 3.44 g (0.02 mol), was added under stirring to
a solution of 3.28 g (0.02 mol) of anhydride I in 25 ml
of benzene, and the mixture was stirred at room tem-
perature until the reaction was complete (TLC). The
precipitate was filtered off and subjected to additional
purification. Yield 6.59 g (98%), mp 152–154°C,
%
: C 66.03; H 8.51; N 11.79. C H N O . Calculated,
13 20 2 2
%
: C 66.10; H 8.47; N 11.86.
N,N-Diethyl-N′,N′-dimethylbicyclo[2.2.1]hept-5-
ene-endo,endo-2,3-dicarboxamide (Vb). Yield 4.44 g
84%), oily substance, R 0.18 (A). IR spectrum, ν,
(
f
–
1
1
cm : 3070, 1640, 1465, 1265, 1150, 730. H NMR
spectrum (300 MHz), δ, ppm: 6.16 m (1H, 5-H),
–
1
5
3
2
1
.78 m (1H, 6-H), 3.34 m (1H, 2-H), 3.32 m (1H, 3-H),
R 0.74 (A). IR spectrum, ν, cm : 3300, 3060, 1721,
1
f
1
.30 q (2H, CH ), 3.13 q (2H, CH ), 2.96 m (1H, 1-H),
672, 1531, 1320, 1275, 714. H NMR spectrum
2
2
.93 m (1H, 4-H), 2.80 s (3H, CH ), 2.64 s (3H, CH ),
(
300 MHz, DMSO-d ), δ, ppm: 11.66 br.s (1H,
3
3
6
2
.37 d (1H, syn-7-H), 1.19 d (1H, anti-7-H, J =
), 0.93 t (3H, CH ). Found, %:
. Calculated, %:
COOH), 9.96 s (1H, NH), 7.49 d (2H, H ), 7.42 d
arom
3
3
(
2
2H, Harom), 6.19 d.d (1H, 6-H, J = 5.6, J
.9 Hz), 6.04 d.d (1H, 5-H, J = 3.2 Hz), 3.32 d.d
1H, 2-H, J2 = 10.2 Hz), 3.22 d.d (1H, 3-H, J
J3 = 3.3 Hz), 3.06 m (1H, 1-H), 3.01 m (1H, 4-H),
.33 d (1H, syn-7-H), 1.27 d (1H, anti-7-H, J =
.4 Hz). Found, %: C 53.63; H 4.12; N 4.25.
=
7.5 Hz), 1.11 t (3H, CH
C 68.21; H 9.13; N 10.60. C15
3
3
5,6
6,1
3
H N O
24 2 2
4,5
3
3
(
=
C 68.18; H 9.09; N 10.61.
,3
1,2
3
,4
N,N-Dimethyl-endo-3-(morpholinocarbonyl)bi-
cyclo[2.2.1]hept-5-ene-endo-2-carboxamide (Vc).
2
1
8
Yield 5.00 g (90%), mp 177–180°C, R 0.30 (B). IR
f
–
1
C H BrNO . Calculated, %: C 53.57; H 4.17; N 4.17.
15
14
3
spectrum, ν, cm : 3070, 1645, 1465, 1440, 1275,
1240, 1120, 735. H NMR spectrum (300 MHz), δ,
1
Endic acid diamides (general procedure). Amido
acid IV, VI, or VII, 0.02 mol, was dissolved in 20 ml
of anhydrous methylene chloride, 0.02 mol of the cor-
responding amine was added (dimethylamine was used
as a freshly prepared 1.3 M solution in methylene
chloride), the mixture was stirred for 10–15 min, and
ppm: 6.08 m (1H, 5-H), 5.90 m (1H, 6-H), 3.55–3.42
(8H, CH
), 3.51 m (1H, 2-H), 3.46 m (1H, 3-H),
),
2
3.01 m (1H, 1-H), 2.97 m (1H, 4-H), 2.94 s (3H, CH
3
2.70 s (3H, CH ), 1.34 d (1H, syn-7-H), 1.20 d (1H,
3
2
anti-7-H, J = 8.1 Hz). Found, %: C 64.70; H 7.99;
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 7 2007

9
88
PAL’CHIKOV et al.
1
N 10.01. C H N O . Calculated, %: C 64.75; H 7.91;
1540, 1320, 1278, 1120, 735. H NMR spectrum
15
22
2
3
N 10.07.
(300 MHz), δ, ppm: 9.73 s (1H, NH), 7.47–7.35 (4H,
Harom), 6.14 m (1H, 5-H), 6.01 m (1H, 6-H), 3.52–3.42
N,N-Diethyl-endo-3-(morpholinocarbonyl)bi-
cyclo[2.2.1]hept-5-ene-endo-2-carboxamide (Vd).
(
8H, CH ), 3.38 m (1H, 2-H), 3.32 m (1H, 3-H),
2
3
7
.12 m (1H, 1-H), 2.97 m (1H, 4-H), 1.34 d (1H, syn-
-H), 1.21 d (1H, anti-7-H, J = 7.8 Hz). Found, %:
Yield 4.71 g (77%), mp 168–170°C, R 0.58 (B). IR
f
2
–
1
spectrum, ν, cm : 3075, 1650, 1465, 1445, 1280,
250, 1150, 735. H NMR spectrum (200 MHz), δ,
ppm: 6.23 d.d (1H, 5-H), 5.73 d.d (1H, 6-H, J = 5.3,
J4,5 = J = 2.7 Hz), 3.59–3.40 (8H, CH ), 3.34 m
1
C 56.32; H 5.25; N 6.98. C H BrN O . Calculated,
1
9
21
2
3
1
3
%: C 56.30; H 5.19; N 6.91.
5
,6
3
3
6,1
2
Symmetric diamides VIIIa and VIIIb were synthe-
(
(
(
(
1H, 2-H), 3.31 m (1H, 3-H), 3.26 q (2H, CH ), 3.14 q
sized by a similar procedure from endic acid II using
2 equiv of N,N′-dicyclohexylcarbodiimide and 2 equiv
of the corresponding amine; yield 5.26 g (90%)
(VIIIa), 6.02 g (94%) (VIIIb).
2
2H, CH ), 2.99 m (1H, 1-H), 2.93 m (1H, 4-H), 1.36 d
2
2
1H, syn-7-H), 1.20 d (1H, anti-7-H, J 8.0 Hz), 1.12 t
3H, CH ), 0.94 t (3H, CH ). Found, %: C 66.60;
3
3
H 8.52; N 9.19. C H N O . Calculated, %: C 66.67;
1
7
26
2
3
Oxidation of diamides VIIIa–VIIIc with peroxy-
formic or peroxyacetic acid in situ. Diamide VIIIa–
VIIIc, 2 mmol, was dissolved in 5–8 ml of 98%
formic or acetic acid, 0.23 ml (4 mmol) of 50% aque-
ous hydrogen peroxide was added dropwise under
stirring at 0°C, and the mixture was stirred at that
temperature until the reaction was complete (TLC).
Volatile substances were removed under reduced pres-
sure, the oily residue was treated with diethyl ether and
thoroughly ground in the cold, and the precipitate was
filtered off and dried. We thus isolated compounds
XI–XIII [19, 20].
H 8.50; N 9.15.
N,N,N′,N′-Tetraethylbicyclo[2.2.1]hept-5-ene-
endo,endo-2,3-dicarboxamide (VIIIa). Yield 5.02 g
(
86%), mp 133–135°C, R 0.22 (A), 0.67 (B). IR spec-
f
–
1
trum, ν, cm : 3058, 1642, 1630, 1462, 1426, 1278,
1
1
258, 1140, 718. H NMR spectrum (300 MHz), δ,
ppm: 5.98 m (2H, 5-H, 6-H), 3.38 m (2H, 2-H, 3-H),
3
4
7
.29 q (4H, CH ), 3.18 q (4H, CH ), 2.93 m (2H, 1-H,
-H), 1.38 d (1H, syn-7-H), 1.18 d (1H, anti-7-H, J =
.8 Hz), 1.08 t (6H, CH ), 0.92 t (6H, CH ). Found, %:
2 2
2
3
3
C 69.91; H 9.52; N 9.64. C H N O . Calculated, %:
C 69.86; H 9.59; N 9.59.
1
7
28
2
2
endo,endo-2,3-Bis(morpholinocarbonyl)bicyclo-
2.2.1]hept-5-ene (VIIIb). Yield 5.57 g (87%),
REFERENCES
[
–
1
1
2
3
. Hargreaves, M.K., Pritchard, J.G., and Dave, H.R.,
Chem. Rev., 1970, vol. 70, p. 439.
. US Patent no. 2462835, 1949; Chem. Abstr., 1949,
mp 219–220°C, R 0.27 (B). IR spectrum, ν, cm :
f
3
040, 1645, 1460, 1435, 1275, 1240, 1120, 735.
1
H NMR spectrum (300 MHz), δ, ppm: 6.01 m (2H,
vol. 43, p. 4421.
5
-H, 6-H), 3.52–3.42 (16H, CH ), 3.33 m (2H, 2-H,
2
. Kas’yan, L.I., Krishchik, O.V., Umrykhina, L.K., and
Kas’yan, A.O., Vіsn. Dnіpropetr. Univ., Khіm., 1998,
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3
-H), 2.97 m (2H, 1-H, 4-H), 1.34 d (1H, syn-7-H),
2
1.21 d (1H, anti-7-H, J = 8.1 Hz). Found, %: C 63.81;
H 7.55; N 8.69. C H N O . Calculated, %: C 63.75;
1
7
24
2
4
4
5
. Augustin, M. and Kuppe, K., Z. Chem., 1974, vol. 14,
p. 306; Ref. Zh., Khim., 1975, no. 2Zh303.
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tyi, S.I., Tarabara, I.N., and Pal’chikov, V.A., Vopr.
Khim. Khim. Tekhnol., 2004, no. 2, p. 35.
H 7.50; N 8.75.
endo,endo-2,3-Bis(perhydroazepin-1ylcarbonyl)-
bicyclo[2.2.1]hept-5-ene (VIIIc). Yield 5.37 g (78%),
mp 149–151°C, R 0.17 (A), 0.63 (B). IR spectrum, ν,
f
–1
cm : 3070, 1635, 1450, 1430, 1270, 1250, 1170, 730.
6
7
8
9
. JPN Patent no. 9319, 1964; Ref. Zh., Khim., 1968,
1
H NMR spectrum (300 MHz), δ, ppm: 5.98 m (2H,
no. 21N595P.
5
1
-H, 6-H); 3.41 m (2H, 2-H, 3-H); 3.29–3.16, 1.74–
. Gray, A.P. and Heitmeier, D.E., J. Org. Chem., 1969,
.59, 1.47, 1.14–0.98 (24H, CH ); 2.97 m (2H, 1-H,
2
vol. 34, p. 3253.
4
-H); 1.37 d (1H, syn-7-H); 1.18 d (1H, anti-7-H,
. Saigo, K., Okuda, Y., Wakabayashi, S., Hoshiko, T., and
Nohira, H., Chem. Lett., 1981, vol. 10, p. 857.
2
J = 7.4 Hz). Found, %: C 73.33; H 9.28; N 8.19.
C H N O . Calculated, %: C 73.26; H 9.30; N 8.14.
21
32
2
2
. Kas’yan, L.I., Krishchik, O.V., Pal’chikov, V.A., and
Tarabara, I.N., Vіsn. Dnіpropetr. Univ., Khіm., 2004,
no. 10, p. 10.
N-p-Bromophenyl-endo-3-(morpholinocarbonyl)-
bicyclo[2.2.1]hept-5-ene-endo-2-carboxamide
(
(
VIIId). Yield 3.40 g (42%), mp 182–185°C, R 0.21
B). IR spectrum, ν, cm : 3280, 3020, 1670, 1645,
10. Gallo, E.A. and Gellman, S.H., Tetrahedron Lett., 1992,
f
–
1
vol. 33, p. 7485.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 7 2007

ENDIC ACID DIAMIDES. SYNTHESIS AND REACTIVITY
989
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