Synthesis and some reactions of new N-[aryl(benzyl, cyclohexyl, propyl)sulfonyl]-4-azatricyclo[5.2.1.02,6]dec-8-enes

Article abstract of DOI:10.1023/B:RUJO.0000013138.30581.5a

A synthesis was accomplished of 4-azatricyclo[5.2.1.0^2,6]dec-8- ene by aminolysis of bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboxylic acid anhydride followed by transformation of amidoacid into imide that was subsequently reduced by lithium aluminum hydride. The reaction of the key tricyclic amine with sulfonyl chlorides afforded N-[aryl(benzyl, cyclohexyl, propyl)sulfonyl]-4-azatricyclo[5.2.1.0^2,6]dec-8-enes.The sulfonamides were subjected to epoxidation with perphthalic acid. By reaction of sulfonamides with p-nitrophenyl azide triazolines were obtained. The structure of compounds synthesized was confirmed by IR, ¹H and ¹³C NMR spectra.

Full text of DOI:10.1023/B:RUJO.0000013138.30581.5a

Russian Journal of Organic Chemistry, Vol. 39, No. 11, 2003, pp. 1629 1635. Translated from Zhurnal Organicheskoi Khimii, Vol. 39, No. 11, 2003,
pp. 1698 1704.
,
,
Original Russian Text Copyright
2003 by L. Kas yan, Tarabara, A. Kas yan, Yarovoi.
Synthesis and Some Reactions of New N-[Aryl(Benzyl,
Cyclohexyl, Propyl)sulfonyl]-4-azatricyclo[5.2.1.02,6]dec-8-enes
L. I. Kas,yan1, I. N. Tarabara1, A. O. Kas,yan2, and
M. Yu. Yarovoi1
1Dnepropetrovsk National University, Dnepropetrovsk, 49050 Ukraine
2Rheinische-Westfaelische Technische Hochschule, Aahen, Germany
Received May 15, 2002
Abstract A synthesis was accomplished of 4-azatricyclo[5.2.1.02,6]dec-8-ene by aminolysis of bicyclo-
[2.2.1]hept-2-ene-endo,endo-5,6-dicarboxylic acid anhydride followed by transformation of amidoacid into
imide that was subsequently reduced by lithium aluminum hydride. The reaction of the key tricyclic amine
with sulfonyl chlorides afforded N-[aryl(benzyl, cyclohexyl, propyl)sulfonyl]-4-azatricyclo[5.2.1.02,6]dec-
8-enes.The sulfonamides were subjected to epoxidation with perphthalic acid. By reaction of sulfonamides
with p-nitrophenyl azide triazolines were obtained. The structure of compounds synthesized was confirmed
by IR, 1H and 13C NMR spectra.
Already about 50 years have passed since the first
publications on the synthesis of 4-azatricyclo-
[5.2.1.02,6]dec-8-ene (I). However among its deriv-
atives mainly alkylation products and salts were
investigated; the latter showed considerable biological
activity (hypotensive, tranquilizing, and ganglio-
plegic) [1]. A number of sulfonylureas was prepared
from the key amine I that showed promise in diabetes
treatment[2, 3]. Among the amine derivatives were
also found substances active against gram-positive
and gram-negative bacteria [4], and also morphine
antagonists [5].
chloride, sodium hydroxide) [10]. In keeping with
the previously obtained data on the dependence on the
structure of the neurotropic activity of sulfonamides
from the other cage-like amines [8, 11] we applied
predominantly aromatic sulfonyl chlorides IIa k.
The only described sulfonamide, N-phenylsulfon-
yl-4-azatricyclo[5.2.1.02,6]dec-8-ene, is insufficiently
investigated, and the range of its biological activity is
not outlined [6, 7]. Incidentally, the related aryl-
sulfonamides, derivatives of 5-aminomethylbicyclo-
[2.2.1]hept-2-enes, possess a considerable neurotropic
(analgetic, anticonvulsant, tranquilizing) and also
antiphlogistic activity [8]. In that connection the goal
of the present research consisted in preparation of
sulfonamides from 4-azatricyclo[5.2.1.02,6]dec-8-ene
and investigation of their reactions at the strained
double bond [9].
Ar = C6H4F-p (IIa), C6H4Cl-p (IIb), C6H4Br-p
(IIc), C6H4NO2-p (IId), C6H4NO2-m (IIe),
C6H3(NO2)2-o,p (IIf), C6H3OCH3-o), NO2-m
(IIg), C6H3CH3-o), NO2-p (IIh), C6d3NO2-o),
CH3-p (IIi), C6H2(i-Pr)3-o,o ,p (IIj), C6H4OCH3-p
(IIk).
Amine (I) was prepared along the previously
described protocol from the bicyclo[2.2.1]hept-2-ene-
endo,endo-5,6-dicarboxylic acid anhydride.
The reaction of amine I with sulfonyl chlorides
was carried out in a two-phase system (ether water)
at equimolar ratio of reagents (amine, sulfonyl
From amine I and toluene-3,4-disulfonyl di-
chloride sulfonamide IIl was obtained.
1070-4280/03/3911-1629$25.00 2003 MAIK Nauka/Interperiodica

1630
KAS,YAN et al.
Table 1. Yields, melting points, IR spectra, and elemental analyses of compounds IIa l, IIIa c
Found,%
Calculated,%
Compd. Yield,
mp,
C
1
IR spectrum, cm
Formula
H16FNO2S
no.
%
C
H
N
C
H
N
IIa
80
104 105
3066, 3050, 1591, 1494,
1346, 1324, 1170, 1153,
713
61.43 5.46 4.78
IIb
IIc
81
80
101 102
103 104
C15H16ClNO2S
C15H16BrNO2S 50.85 4.52 3.95
58.16 5.17 4.52
3070, 1569, 1469, 1340,
1168, 1143, 1011, 793,
748
IId
93
178 179
3065, 1527, 1463, 1348, 56.38 4.94
1167, 738
8.85 C15H16N2O4S
C15H16N2O4S
56.25 5.00 8.75
IIe
IIf
85
79
115 116
88 90
56.25 5.00 8.75
49.32 4.11 11.51
1563, 1478, 1380, 1359, 49.41 4.21 11.59 C15H15N3O6S
1183, 1074, 730
IIg
IIh
78
82
155 156
107 108
3085, 1530, 1492, 1352, 54.98 5.22
1340, 1172, 1157, 1076,
723
3092, 1535, 1488, 1357, 57.57 5.49
1334, 1170, 1148, 1089,
758
8.09 C16H18N2O5S
54.86 5.14 8.00
57.49 5.39 8.38
8.47 C16H18N2O4S
IIi
IIj
77
74
111 112
157 158
57.54 5.47
3078, 1610, 1481, 1370, 71.74 8.84
1335, 1170, 1079, 721
8.50 C16H18N2O4S
3.57 C24H35NO2S
57.49 5.39 8.38
71.82 8.73 3.49
IIk
IIl
79
83
67 68
184 186
C16H19NO3S
5.69 C25H30N2O4S2
62.95 6.23 4.59
61.73 6.17 5.76
3060, 1483, 1356, 1179, 61.68 6.26
1153, 1088, 722
IIIa
IIIb
IIIc
76
57
69
133 135
90 91
3069, 1598, 1491, 1330,
1150, 1060, 705
3083, 1478, 1325, 1155, 64.16 8.09
1142, 1095, 720
C16H19NO2S
5.05 C15H23NO2S
C12H19NO2S
66.44 6.57 4.84
64.06 8.18 4.98
59.75 7.88 5.81
Oilysubstance 3065, 1325, 1158, 1057,
723
For the sake of comparison we carried out also
reactions with benzyl-, cyclohexyl-, and propylsul-
fonyl chlorides which furnished compounds IIIa c.
The characteristics of sulfonamides obtained and
the data of their IR spectra are compiled in Table 1.
All compounds synthesized contain a strained double
bond appearing in the IR spectra as absorption bands
in the regions 1575 1550, 3065 3040 and 735
1
700 cm ( C=C, = C H, = C H respectively)
[9]. The unusual position of the first band is due to
the strain in the double bond leading to decrease in
the factor of the kinematic interaction of C=C and
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 11 2003

SYNTHESIS AND SOME REACTIONS
Table 2. 1H NMR spectra , ppm, coupling constants, Hz
1631
Compd. H8, H9
no.
H1, H7
H2, H6
H3A, H3B
H5A, H5B
H10S, H10A
H arom
2
2
I
6.20
5.93
5.95
5.98
5.94
5.97
6.08
6.17
6.12
5.99
6.34
2.82
2.72
2.72
2.75
2.79
2.79
2.82
2.84
2.68
2.65
2.88
2.70
2.76
2.82
2.80
2.79
2.80
2.85
2.86
2.84
2.80
2.88
2.68, 2.57, J 11.7 2.68, 2.57
1.46, 1.42, J 7.8
2
IIa
IIb
IIc
IId
IIe
IIg
IIh
IIj
3.07, 2.78
3.05, 2.83
3.07, 2.82
3.10, 2.85
3.13, 2.82
3.29, 2.97
3.28, 3.00
3.19, 2.92
3.03, 2.82
3.25, 2.96
3.07, 2.78
3.05, 2.83
3.07, 2.82
3.10, 2.85
3.13, 2.82
3.27, 3.95
3.28, 3.00
3.19, 2.92
2.97, 2.82
3.25, 2.96
1.46, 1.31, J 8.5
7.70, 7.13
7.68, 7.56
7.70, 7.55
8.30, 7.86
8.45 7.88
8.49 7.38
8.46 7.62
7.07
1.45, 1.35
1.48, 1.35
2
1.48, 1.32, J 8.5
1.47, 1.34
1.50, 1.36
1.55, 1.45
1.57, 1.47
1.50, 1.38
1.50, 1.42
IIk
IIIb
7.55, 6.98
Table 3. 13C NMR spectra of N-substituted 4-azatricyclo[5.2.1.02,6]dec-8-enes and their epoxy derivatives, , ppm.
Compd.
no.
C8, C9
C1, C7
C2, C6
C3, C5
C10
C arom
IIa
IId
IIg
IVa
IVc
IVd
IVf
IVg
IVh
135.3
135.8
135.8
49.6
49.6
49.4
49.7
49.3
49.4
45.9
45.9
46.2
40.8
40.8
40.8
40.5
40.7
40.9
46.3
46.4
46.5
44.1
44.1
44.1
44.2
44.7
44.8
50.5
50.6
50.5
48.2
48.3
48.3
48.1
48.1
48.2
52.6
52.6
52.5
29.6
29.6
29.6
29.9
20.8
29.8
166.5, 63.9, 30.4, 16.4
150.2, 142.6, 128.8, 124.3
161.6, 140.7, 128.9, 129.7, 127.4, 112.5
166.7, 164.1, 130.7, 116.6
140.4, 134.1, 132.5, 129.4
150.4, 141.2, 129.1, 124.5
153.4, 151.6, 136.2, 124.1
130.7, 129.3, 128.9
C C bonds that is proportional to the cosine of the
angle between them. This band is of low intensity
because of the high degree of symmetry in the frag-
ment. Both the first and the second of the mentioned
bands are overlapped by the absorption bands of the
benzene ring. The characteristic absorption band of
the norbornene double bond is observed in the region
Molecules of all compounds are in a symmetrical
or nearly symmetrical conformation where the
chemical shifts are equal in the pairs of protons H8
and H9, H1 and H7, H2 and H6, H3 and H5. In the
molecule of amine I and its derivatives the protons
in the methylene groups at C3 and C5 carbons (H3A
and H3B, H5A and H5B) are nonequivalent. The
bridging protons H10s and H10a appear in an AB-
system pattern, and their nonequivalence in the sul-
fonamide molecules is considerably more pro-
nounced than in amine I. The comparison with the
spectrum of amine I showed that the introduction
of an electron-withdrawing sulfonyl group and
electron-withdrawing substituents into the benzene
ring first of all affected the proton signals in the
neighboring methylene groups at C3 and C5 carbons,
and also signals of protons attached to C2 and
C6 carbons further on along the carbon carbon
chain.
1
730 700 cm in contrast to the other unsaturated
systems. In the spectra of sulfonamides the bands of
N H groups are lacking, and are present the absorp-
tion bands of sulfonyl group 1350 1320 and 1170
1
1140 cm ) and of substituents in the benzene ring:
1
nitro group (1560 1520 and 1375 1335 cm ) and
1
methoxy group (2850 cm ) [12].
To confirm the structure of compounds we
1
measured the H and 13C NMR spectra. In Table 2
are listed the parameters of proton spectra of com-
pounds IIa k, IIIb, and for comparison also that of
amine I.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 11 2003

1632
Table 4. Yields, melting points, IR spectra, and elemental analyses of epoxy derivatives IVa h
KAS,YAN et al.
Compd.
no.
Found,%
H
Calculated,%
Yield,
%
mp,
(2-propanol)
C
1
IR spectrum, cm
Formula
C
N
C
H
N
IVa
71
172.5 173.5 3065, 3034, 1588, 1492, 58.19 5.08 4.55 C15H16FNO3S
1346, 1152, 853
58.25 5.18 4.53
IVb
IVc
87
72
162 163
157 158
4.27 C15H16ClNO3S
55.30 4.92 4.30
3050, 3037, 1573, 1345, 48.77 4.42 3.85 C15H16BrNO3S 48.65 4.32 3.78
1328, 1167, 1025, 852
IVd
85
216 218
3066, 3026, 1528, 1349, 53.52 4.70 8.28 C15H16N2O5S
1302, 1172, 1152, 853
53.57 4.76 8.33
IVe
IVf
73
74
176 177
190 191
8.29 C15H16N2O5S
3.42 C24H35NO3S
53.57 4.76 8.33
69.06 8.39 3.36
3040, 1603, 1363, 1329,
1164, 1037, 855
3032, 1329, 1168, 1144,
1040, 848
IVg
IVh
95
71
164 165
159 160
4.57 C16H19NO3S
62.95 6.23 4.59
60.61 7.74 4.71
3045, 1318, 1135, 1049, 60.63 7.61 4.77 C15H23NO3S
855
Parameters of 13C NMR spectra of sulfonamides
IIa, d, g are listed in Table 3; the assignment was
performed by Rabenstein and Nakashima procedure.
The olefin carbons give rise to signals at 135.8 ppm;
as in the proton spectra, all twin nuclei have
signals with equal chemical shifts; the most downfield
signals correspond to bridging carbons (52.5
52.6 ppm) and to C3 and C5 (50.5 ppm).
The obtained sulfonamides containing a strained
double bond [9] were subjected to reactions resulting
in this bond functionalization, with peracids and aryl
azides. As epoxidizing agent we chose the perphthalic
acid in statu nascendi prepared from phthalic an-
hydride and 30% water solution of hydrogen per-
oxide. The reaction was carried out in ethyl acetate
in the presence of carbamide used to adjust the
proton-donor and proton-acceptor quality of the
medium [13]. The reaction progress was monitored
by TLC.
The characteristics of the epoxides obtained are
given in Table 4. All compounds prepared except
derivative IVi are crystalline. The IR spectra contain
absorption bands in the region 855 848 and 3045
1
3020 cm
( C O and C H in epoxynorbornanes
[10, 14]). No absorption was observed in the range
1
3400 3200 cm ( OH, NH), and appeared bands
characteristic of SO2 group (1350 1320 and 1175
1
1135 cm ) and of bonds in the benzene ring and its
substituents, in particular, of nitro group (1560 1520
1
and 1340 1305 cm ) [12].
The structure of epoxides was unambiguously con-
1
firmed by their H and 13C NMR spectra (Tables 3,
5, figure). The signals were assigned with the help of
two-dimensional spectra COSY and HECTOR. The
1H NMR spectra of epoxides IVa, c, d, f h lack
signals at 6 ppm, and at 3.14 3.38 ppm appear
signals of the protons of the epoxy ring sensitive to
a certain extent to the character of the solvent. The
shift of the signal belonging to one of the bridging
hydrogens (H10A) to 0.7 0.8 ppm confirms theexo-
orientation of the epoxy ring [15].
In the 13C NMR spectra (Table 3) appear the
signals of carbon atoms from the epoxy ring (C8, C9)
in the region 49.3 49.7 ppm. In keeping with [16] the
signals of the bridging carbons (C10) are shifted
upfield (29.6 29.9 ppm) compared to the unsaturated
compounds. This shift is an additional proof of the
exo-orientation of the epoxy ring. In the 13C NMR
spectra are also observed the resonances of carbon
R = C6H4F-p (IVa), C6H4Cl-p (IVb), C6H4Br-p
(IVc), C6H4NO2 p (IVd), C6H4NO2-m (IVe),
C6H2(i-Pr)3-o,o p (IVf), CH2C6H5 (IVg), C6H11-cyclo
(IVh), C3H7 (IVi).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 11 2003

SYNTHESIS AND SOME REACTIONS
1633
1H NMR spectrum of N-benzylsulfonyl-exo-8,9-epoxy-4-azatricyclo-[5.2.1.02,6]decane.
atoms belonging to the substituents (substituted benz-
ene rings and a cyclohexyl moiety).
The sulfonamides synthesized were brought into
reaction with equimolar amount of p-nitrophenyl
azide at reflux in chloroform (TLC monitoring).
Reactions of compound I with azides were not
studied before in contrast to the first member of the
series, norbornene [17]. Due to the high strain in the
double bond the latter readily reacted with various
azides, and depending on the type of azide the reac-
tions afforded substituted triazolines, aziridines, or
products of their subsequent transformations. Among
these substances biologically active compounds were
revealed [18]. The reaction mechanism of norbornene
and its derivatives involved formation of a five-
membered activated complex, and these processes
could be classed among [3+2]cycloadditions. Unlike
norbornene the disubstituted norbornenes were
seldom brought into reactions with azides [18, 19].
The characteristics of triazolines Va e are listed in
Table 6. In the IR spectra of the compounds alongside
the absorption bands originating from the structure
of the initial tricyclic alkenes appeared new bands
1
in the regions 1520 1500 and 1350 1320 cm
belonging to nitro groups [12], and also medium
1
bands at 1595 cm presumably corresponding to
stretching vibrations of unsymmetrically substituted
N=N band of the triazoline moiety [20]. The struc-
ture of compounds Va, c e was supported by the
1H NMR spectra (Table 5) containing doublets in the
region 4.90 4.70 and 4.80 4.05 ppm with a vicinal
coupling constant 9 Hz corresponding to protons H8,
H9 of the triazoline moiety [21]. The shift of one of
the bridging protons (H10A) signal to 0.95 0.85 ppm
evidences exo-orientation of the triazoline moiety.
EXPERIMENTAL
IR spectra were recorded on spectrometer Specord
1
IR75 from samples pelletized with KBr. H NMR
spectra were registered on spectrometers Varian
VXR-300 and Inova-400 at operating frequencies 300
and 400 MHz respectively from solutions in deutero-
Ar = C6H4F-p (Va), C6H5Br-p (Vb), C6H4NO2-p
(Vc), C6H2(i-Pr)3-o,o ,p (Vd), CH2C6H5F (Ve).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 11 2003

1634
Table 5. H NMR spectra of compounds IVa, c, d, f h, Va, c e, , ppm, coupling constants, Hz
KAS,YAN et al.
1
Compd. no.
IVa
H8, H9
3.25
3.25
3.21
3.14
3.18
3.38
H1, H7
2.52
2.52
2.50
2.50
2.46
2.62
2.46
2.32
2.68
2.46
H2, H6
2.52
2.52
2.59
2.66
2.53
2.72
2.58
2.60
2.80
2.66
H3A, H3B
H3A, H3B
H10S, H10A
H arom
7.72, 7.15
7.71, 7.56
8.44, 8.00
7.09
3.43, 2.64 3.41, 2.62 1.40, 0.70,
2J 10.2
3.44, 2.63 3.42, 2.60 1.40, 0.70,
2J 10.1
IVc
IVd
IVf
3.39, 2.78 3.39, 2.76 1.21, 0.74,
2J 9.6
3.27, 2.89 3.25, 2.89 1.40, 0.76,
2J 10.1
3.36, 2.83 3.34, 2.80 1.37, 0.69,
IVg
7.30
2J 9.9
IVh
Va
3.59, 3.23 3.59, 3.23 1.49, 0.82,
2J 9.8
4.90, 4.04,
3J8,9 9.0
3.76, 2.77, 3.56, 2.75 1.46, 0.93,
8.20 7.50
8.40 8.00
2J3,5 10.3
2J 9.9
Vc
4.92, 4.05,
3.80, 2.98 3.63, 2.98 1.44, 0.94,
3J8,9 9.0
2J 10.0
Vd
4.70, 3.97,
3J8,9 8.7
3.64, 3.02, 3.45, 2.99 1.32, 0.94,
8.10, 7.39, 7.19
8.18, 7.42, 7.24
2J3,5 10.1
2J 11.0
Ve
4.72, 3.77,
3.61, 3.04, 3.49, 2.97 1.27, 0.84,
3J8,9 8.8
2J3,5 10.5 2J 10.8
Table 6. Yields, melting points, IR spectra, and elemental analyses of triazolines Va e
Compd. Yield,
Found,
N, %
Calculated,
N, %
1
no.
%
mp,
C
IR spectrum, cm
Formula
Va
Vb
Vc
79
78
77
235 237 (decomp.) 1595, 1505, 1354, 1320, 1176, 1085, 838 15.36 C21H20FN5O4S
15.32
13.51
17.36
234 236 (decomp.)
13.45 C21H20BrN5O4S
17.48 C21H20N6O6S
240 242 (decomp.) 1584, 1520, 1500, 1348, 1318, 1180,
1089, 850
Vd
Ve
76
85
207 209 (decomp.) 1595, 1501, 1375, 1324, 1165, 1077, 844 12.46 C30H39N5O4S
193 195 (decomp.) 1596, 1501, 1378, 1335, 1172, 1147, 844 15.34 C22H23N5O4S
12.39
15.45
chloroform, internal reference HMDS. 13C NMR
spectra were measured on spectrometer Inova-400 at
operating frequency 100.6 MHz. Some spectra were
registered by COSY and HECTOR procedures. The
reaction progress was monitored and the purity of
compounds synthesized was checked by TLC on
Silufol UV-254 plates, eluent ether, development in
iodine vapor. Elemental analysis was carried out on
Karlo Erba analyzer.
4-Azatricyclo[5.2.1.02,6]dec-8-ene (I) was prepared
by procedures [3, 6]; the characteristics of compound
obtained were in agreement with the published data.
N-[Aryl(benzyl, cyclohexyl, propyl)sulfonyl]-4-
azatricyclo[5.2.1.02,6]dec-8-enes (IIa k, IIIa c). To
a stirred mixture of 0.3 g (2.2 mmol) of amine I and
0.4 ml (2.2 mmol) of 20% water solution of sodium
hydroxide in 15 ml of ether was added dropwise a
solution of 2.2 mmol of an appropriate aryl(cyclo-
hexyl, benzyl, propyl)sulfonyl chloride in 10 ml of
ether. The reaction mixture was stirred at room
temperature till completion of the reaction (TLC
monitoring). The solvent was removed, the residue
was dissolved in 20 ml of chloroform water mixture
(1: 1), the organic layer was separated, dried with
calcined magnesium sulfate, the solvent was removed,
and the residue was recrystallized from 2-propanol.
The physical properties and spectral parameters of
compounds IIa l, IIIa c are given in Tables 1 3.
N-[Aryl(benzyl, cyclohexyl, propyl)sulfonyl]-
exo-8, 9-epoxy-4-azatricyclo[5.2.1.02,6]decanes
(IVa i). To a mixture of 0.6 mmol of an appropriate
sulfonamide, 0.18 g (1.2 mmol) of phthalic anhydride,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 11 2003

SYNTHESIS AND SOME REACTIONS
1635
and 0.02 g (0.3 mmol) of urea in 15 ml of ethyl
acetate was added at room temperature under stirring
0.1 ml (1.2 mmol) of 35% water solution of hydro-
gen peroxide. The stirring was continued till comple-
tion of the reaction (TLC monitoring). On neutraliz-
ing the reaction mixture with saturated solution of
sodium hydrogen carbonate the organic layer was
separated, dried with calcined magnesium sulfate, the
solvent was removed, and the residue was recrystal-
lized from 2-propanol. The physical properties and
spectral parameters of compounds IVa i are given in
Tables 4, 5.
vol. 67, p. 299; Onishchenko, A.S., Dienovyi sintez
(Dienic Synthesis), Moscow: Izd. Akad. Nauk SSSR,
1963.
10. Kas,yan, L.I., Gorb, L.G., and Klebanov, B.M.,
Zh. Org. Khim., 1995, vol. 31, p. 678; Kasyan, L.I.,
Sereda, S.V., Potekhin, K.A., and Kasyan, A.O.,
Heteroatom Chem., 1997, vol. 8, p. 177.
11. Zlenko, H., Kasyan, L., Mamchur, V., Kasyan, A.,
Podpletnyaya, H., Tarabara, I., and Krishchik, O.,
Fundam. and Clinical Pharm., 1999, vol. 13, p. 377;
Zlenko, E.T., Kas,yan, L.I., Mamchur, V.I.,
Demchenko, E.M., Kas,yan, A.O., and Taraba-
ra, I.N., Abstracts of Papers, Rossiiskaya nauchno-
prakt. konf. Patologicheskaya bol, (Russian Sci.
Conf. on Pathological Pain), Novosibirsk, 1999,
p. 212.
Products of reaction between sulfonamides and
aryl azides Va e. A mixture of 1 mmol of an ap-
propriate sulfonamide and 0.16 g (1 mmol) of p-nitro-
phenyl azide was heated to reflux in 10 ml of chloro-
form till the completion of reaction (TLC monitor-
ing). The separated precipitate was filtered off and
recrystallized from aqueous acetone. The physical
properties and spectral parameters of compounds
Va e are presented in Tables 5, 6.
12. Nakanisi, K., Infrakrasnye spektry organicheskikh
soedinenii (IR Spectrua 0f Organic Compounds),
Moscow: Mir, 1965.
13. Dryuk, V.G., Kartsev, V.G., and Voitsekhov-
skaya, M.A., Oksirany
sintez i biologicheskaya
aktivnost, (Oxiranes: Synthesis and Biological
Activity Moscow: Bogorodskii pechatnik, 1999.
14. Kas,yan, L.I., Zh. Org. Khim., 1999, vol. 35, p. 661;
Kas,yan, L.I., Seferova, M.F., and Okovityi, S.I.,
Alitsiklicheskie epoksidnye soedineniya. Metody
sinteza (Alicyclic Epoxide Compounds. Methods of
Synthesis), Dnepropetrovsk: Dnepropetrovsk. Gos.
Univ., 1996.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 11 2003