Reactions of N,N-(dialkyl)arylthioacetamides with dialkyl acetylenedicarboxylates

Article abstract of DOI:10.1023/A:1015868201847

2-(Alkoxycarbonylmethylidene)-4-aryl-5-(dialkylamino)thiophen-3(2H)-ones were synthesized by condensation of N,N-(dialkyl)arylthioacetamides with dialkyl acetylenedicarboxylates. Intermediate substituted vinylic sulfides were isolated. When heated or in t

Full text of DOI:10.1023/A:1015868201847

Russian Chemical Bulletin, International Edition, Vol. 51, No. 4, pp. 653—658, April, 2002
653
Reactions of N,Nꢀ(dialkyl)arylthioacetamides
with dialkyl acetylenedicarboxylates
a
aꢀ
b
b
M. F. Kosterina, Yu. Yu. Morzherin, A. V. Tkachev, T. V. Rybalova,
b
a
Yu. V. Gatilov, and V. A. Bakulev
aUral State Technical University,
1
9 ul. Mira, 620002 Yekaterinburg, Russian Federation.
Eꢀmail: morjerine@htf.ustu.ru
b
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry,
Siberian Branch of the Russian Academy of Sciences,
9
prosp. Akad. Lavrent´eva, 630090 Novosibirsk, Russian Federation.
Eꢀmail: atkachev@nioch.nsc.ru
2
ꢀ(Alkoxycarbonylmethylidene)ꢀ4ꢀarylꢀ5ꢀ(dialkylamino)thiophenꢀ3(2H)ꢀones were synꢀ
thesized by condensation of N,Nꢀ(dialkyl)arylthioacetamides with dialkyl acetyleneꢀ
dicarboxylates. Intermediate substituted vinylic sulfides were isolated. When heated or in the
presence of an acid or a base, they undergo cyclization into thiophenes.
Key words: thiophene, N,Nꢀ(dialkyl)arylthioacetamides, dialkyl acetylenedicarboxylates,
condensation.
The reactions of thioureas, thiosemicarbazides, and
Scheme 1
thioamides with acetylenedicarboxylic acid derivatives are
convenient methods for the synthesis of nitrogenꢀ and
1
—9
1—5
sulfurꢀcontaining heterocycles
such as thiazoles,
6
,7
8
9
thiazines, imidazoles, thiadiazines, and pyrimidines.
However, only nonsubstituted or Nꢀmonosubstituted deꢀ
rivatives of thioureas, thiosemicarbazides, and thioamides
were involved in this reaction. The goal of the present
study is to investigate the reactions of N,Nꢀ(dialkyl)arylꢀ
thioacetamides with dialkyl acetylenedicarboxylates.
Results and Discussion
The reactions of 2ꢀarylthioacetamides 1a—i with
acetylene derivatives yielded only substituted 2ꢀmethylꢀ
idenethiophenꢀ3ꢀones 2a—j (Scheme 1), which were
1
13
identified using IR and H and C NMR spectroscopy
and mass spectrometry (Tables 1—3).
13C NMR data enable one to exclude the formation
of possible products 3. Thus, a signal from the C(4) atom
shows a splitting only for the orthoꢀhydrogen atoms of
the phenyl group, and JC(3)—H(6) = 4.6 Hz, which indiꢀ
cates the (Z)ꢀconfiguration of the exocyclic double bond,
JC(8)—H(6) being equal to 1.9 Hz. The structure of comꢀ
pound 2j was confirmed by Xꢀray diffraction data
for a single crystal obtained by crystallization from
ethanol.
Comꢀ
pound
1, 2
2
R´
Comꢀ
pound
1f, 2f
1, 2
2
R´
Et
X
O
O
O
O
O
R
X
O
R
OEt
H
1
1
1
a, 2a
b, 2b
c, 2c
OMe Me
Cl
Br
H
Me
Me
Me
Et
1g, 2g CH2
1h, 2h CH2 OMe Me
1i, 2i CH2
2j CH2
Me
1d, 2d
1e, 2e
Cl
H
Me
Et
Me
fragments are planar with an accuracy of ±0.016(2) Å,
and the whole molecule, except for the phenyl and pipeꢀ
ridine groups, is planar with an accuracy of ±0.228(6) Å.
Two crystallographically independent molecules of
compound 2j are very close in geometry. Their thiophene
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 604—608, April, 2002.
066ꢀ5285/02/5104ꢀ653 $27.00 © 2002 Plenum Publishing Corporation
1

654
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 4, April, 2002
Kosterina et al.
Table 1. Characteristics of the starting thioacetamides 1 and 4
Comꢀ
pound
M.p./°C
Yield (%)
Found
Calculated
Molecular formula
MS,
[M]
(
%)
S
+
N
1
1
1
1
1
1
1
1
1
4
4
4
a
b
c
d
e
f
70
85
69
48
52
38
75
47
65
36
57
69
38
55
—
13.08
2.76
12.81
2.54
10.89
0.68
14.86
4.49
13.85
3.63
12.28
2.08
15.08
4.62
12.98
2.86
13.01
2.63
C H17NO2S
251
255
1
3
1
—
—
—
—
—
—
—
—
C12H ClNOS
14
1
70
C H14BrNOS
301, 299
221
1
2
1
100
105
80
C H15NOS
12
1
C H17NOS
235
1
3
1
C H NO S
265
1
4
19
2
1
g
h
i
80
C H17NS
219
1
3
1
70
C H NOS
249
1
4
19
1
60
C H ClNS
253
1
3
16
1
a
b
c
95
16.55
6.46
16.41
6.65
18.32
8.16
18.69
18.84
18.95
19.06
21.12
20.79
C H N OS
170
7
10
2
1
65
C H N S
168
8
12
2
1
100
C H N S
154
7
10
2
1
Table 2. Characteristics of compounds 2, 5, and 6
Comꢀ
pound
M.p./°C
Yield (%)
Found
Calculated
Molecular formula
MS,
[M]
(
%)
S
+
N
2
2
2
2
2
2
2
2
2
2
5
a
b
c
d
e
f
160
215
220
150
220
145
140
155
185
141
165
45
51
62
42
54
47
56
52
48
53
57
4.12
.88
3.98
.83
3.74
.41
4.43
.23
3.63
.90
3.62
.60
4.10
.25
4.25
.90
4.13
.00
3.90
.08
10.15
.99
8.97
8.86
9.08
8.76
8.11
7.81
9.39
9.68
9.35
8.92
8.14
8.23
9.89
9.73
8.77
8.92
10.05
9.17
8.89
9.33
11.26
11.44
C H NO S
361
365
410
331
359
389
329
359
349
343
280
1
8
19
5
3
C H16ClNO4S
1
7
3
C H BrNO S
1
7
16
4
3
C H17NO4S
1
7
4
C H NO S
1
9
21
4
3
C20H23NO5S
C H N0 S
3
g
h
i
1
8
19
4
4
C H N0 S
1
9
21
4
3
C H16ClNO3S
1
7
4
j
C H NO S
19 21 3
4
a
C12H N O S
12 2 4
9
(
to be continued)

Reactions of N,Nꢀ(dialkyl)arylthioacetamides
Table 2 (continued)
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 4, April, 2002
655
Comꢀ
pound
M.p./°C
Yield (%)
Found
Calculated
Molecular formula
MS,
[M]
(
%)
S
+
N
5
5
5
6
6
b
c
d
a
d
180
240
238
115
96
60
53
85
62
65
10.21
0.06
10.52
0.60
10.25
11.29
11.52
11.82
12.13
11.78
11.52
10.52
10.25
11.22
10.82
C H N O S
278
264
278
312
296
1
3
14
2
3
1
C H N O S
1
2
12
2
3
1
C H N O S
1
3
14
2
3
1
0.06
9.43
C H N O S
1
3
16
2
5
8
.97
9.73
.45
C H N O S
1
3
16
2
4
9
1
Table 3. H NMR spectra of the compounds synthesized
Comꢀ
pound
1H NMR (DMSOꢀd6)
δ (J/Hz)
2
2
2
2
2
2
a
b
c
d
e
f
7.16 (d, 2 H, ArH, J = 6.8); 6.93 (d, 2 H, ArH, J = 6.8); 6.63 (s, 1 H, CH); 3.77 (s, 3 H, OMe);
.76 (s, 3 H, OMe), 3.60—3.64 (m, 4 H, 2 CH ); 3.44—3.48 (m, 4 H, 2 CH )
3
2
2
7.42 (d, 2 H, ArH, J = 6.7); 7.29 (d, 2 H, ArH, J = 6.7); 6.66 (s, 1 H, CH); 3.78 (s, 3 H, OMe);
.60—3.64 (m, 4 H, 2 CH ); 3.44—3.48 (m, 4 H, 2 CH )
3
2
2
7.52—7.56 (m, 2 H, ArH); 7.21—7.24 (m, 2 H, ArH); 6.65 (s, 1 H, CH); 3.77 (s, 3 H, OMe);
.60—3.66 (m, 4 H, 2 CH ); 3.41—3.46 (m, 4 H, 2 CH )
3
2
2
7.30—7.32 (m, 5 H, C H ); 6.65 (s, 1 H, CH); 3.79 (s, 3 H, OMe); 3.60—3.65 (m, 4 H, 2 CH );
6
5
2
3
.40—3.45 (m, 4 H, 2 CH2)
7.10—7.16 (m, 4 H, ArH); 6.61 (s, 1 H, CH); 4.24 (q, 2 H, CH , J = 7.1); 3.58—3.62 (m, 4 H, 2 CH );
2
2
3
.42—3.46 (m, 4 H, 2 CH ); 2.30 (s, 3 H, Me); 1.28 (t, 3 H, Me, J = 7.1)
2
7.10 (d, 2 H, ArH, J = 7.8); 6.84 (d, 2 H, ArH, J = 7.8); 6.63 (s, 1 H, CH); 4.25 (q, 2 H, CH , J = 7.0);
2
4
1
.01 (q, 2 H, CH , J = 7.0); 3.60—3.64 (m, 4 H, 2 CH ); 3.28—3.33 (m, 4 H, 2 CH );
.38 (t, 3 H, Me, J = 7.0); 1.26 (t, 3 H, Me, J = 7.0)
2
2
2
2
2
2
2
g
h
i
7.30—7.40 (m, 5 H, C H ); 6.63 (s, 1 H, CH); 3.76 (s, 3 H, OMe); 3.40—3.44 (m, 4 H, N(CH ) );
6
5
2
2
1
.50—1.60 (m, 6 H, (CH ) )
2 3
7.16 (d, 2 H, ArH, J = 8.9); 6.93 (d, 2 H, Ar, J = 8.9); 6.61 (s, 1 H, CH); 3.77 (s, 3 H, OMe);
.76 (3 H, s, OMe); 3.43 (br.s, 4 H, N(CH ) ); 1.56 (br.s, 6 H, N(CH ) )
3
2
5
2 5
7.42 (d, 2 H, ArH, J = 7.9); 7.28 (d, 2 H, ArH, J = 7.9); 6.62 (s, 1 H, CH); 3.77 (s, 3 H, OMe);
.40—3.44 (m, 4 H, N(CH ) ); 1.55—1.60 (m, 4 H, (CH ) )
3
2
2
2 3
j*
7.28—7.33 (m, 2 H, C H ); 6.20—6.30 (m, 3 H, C H ); 6.84 (s, 1 H, CH); 4.25 (t, 2 H, OCH , J = 7.0);
6 5 6 5 2
3
.73 (t, 4 H, 2 NCH ); 1.53 (tt, 4 H, 2 CH ); 1.59 (tt, 2 H, CH ); 1.30 (q, 3 H, Me, J = 7.0)
2 2 2
5
5
a
b
6.70 (s, 1 H, CH); 3.80—3.84 (m, 4 H, O(CH ) ); 3.75 (s, 3 H, OMe); 1.30—1.35 (s, 4 H, N(CH ) )
2
2
2
2
6.69 (s, 1 H, CH); 4.16—4.20 (m, 2 H, CH ); 3.80 (s, 3 H, OMe); 3.70—3.76 (m, 2 H, CH );
2
2
1
.75—1.81 (m, 6 H, (CH ) )
2 3
5
5
6
6
c
6.68 (s, 1 H, CH); 4.00—4.10 (m, 2 H, CH ); 3.80 (s, 3 H, OMe); 3.75—3.79 (m, 2 H, CH );
2
2
2
.00—2.15 (4 H, m, (CH ) )
2 2
d
6.67 (s, 1 H, CH); 4.20 (q, 2 H, OCH , J = 7.1); 4.00—4.10 (m, 2 H, CH ); 3.75—3.79 (m, 2 H, CH );
2 2 2
2
.00—2.15 (m, 4 H, (CH ) ); 1.28 (q, 3 H, Me, J = 7.1)
2 2
a
6.72 (s, 1 H, CH); 4.85 (s, 1 H, CH); 3.70 (s, 3 H, OMe); 3.74 (s, 3 H, OMe);
.50—3.58 (m, 4 H, O(CH ) ); 3.15—3.19 (m, 4 H, N(CH ) )
3
2
2
2 2
d*
Major product (90%): 6.72 (s, 1 H, CH); 4.36 (s, 1 H, CH); 4.21 (q, 2 H, OCH Me, J = 7.1);
2
4
1
.20 (q, 2 H, OCH Me, J = 7.1); 3.56—3.66 (m, 4 H, 2 CH ); 3.24 (m, 4 H, 2 CH );
.30 (t, 3 H, Me, J = 7.1); 1.28 (t, 3 H, Me, J = 7.1)
2
2
2
Minor product (10%): 6.56 (s, 1 H, CH); 4.32 (s, 1 H, CH); 4.21 (q, 2 H, OCH Me, J = 7.1);
2
4
1
.20 (q, 2 H, OCH Me, J = 7.1); 3.56—3.66 (m, 4 H, 2 CH ); 3.24 (m, 4 H, 2 CH );
.30 (t, 3 H, Me, J = 7.1); 1.28 (t, 3 H, Me, J = 7.1)
2
2
2
*
In CDCl3.

656
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 4, April, 2002
Kosterina et al.
It should be noted that the bond lengths in the
C(5)=C(4)—C(3)=O(7) fragment are equalized (the avꢀ
erage bond lengths for two molecules are 1.389, 1.431,
and 1.226 Å, respectively) and that the S(1)—C(2)
and S(1)—C(5) bonds are not equivalent (average
bond lengths 1.736 and 1.796 Å). The above structural
features were confirmed by MP2/6ꢀ31G* quantumꢀ
chemical calculations for (5ꢀaminoꢀ3ꢀoxoꢀ2Hꢀthioꢀ
phenꢀ2ꢀylidene)acetic acid as a model compound;
bond equalization in the C(5)=C(4)—C(3)=O(7) fragꢀ
ment was noted earlier for structurally close comꢀ
pounds.1
Scheme 2
0,11
Unlike compounds 1a—i, cyanothioacetamides 4a—c
react with dialkyl acetylenedicarboxylates to give not only
thiophenes 5a—d, but also vinylic sulfides 6a,d resulting
from the addition of thioamides to acetylene derivatives
(
Scheme 2).
Sulfide 6d contains an impurity (∼10%), which is
R´ = Me (a—c), CH Me (d)
2
probably a stereoisomer about one of the double bonds.
When heated in ethanol, compounds 6a,d undergo cyꢀ
clization into thiophenes 5a,d. This reaction is also posꢀ
sible at room temperature in the presence of a catalytic
amount of triethylamine or HCl. The structures of all
X = O (a), CH2 (b)
n = 1 (a, b), 0 (c, d)
Hence, N,Nꢀ(dialkyl)arylꢀ and ꢀcyanothioacetamides
react with dialkyl acetylenedicarboxylates to give substiꢀ
tuted 5ꢀmethylidenethiophenꢀ4ꢀones. At the first stage,
acetylene derivatives add to the sulfur atom to form subꢀ
stituted vinylic sulfides, which undergo cyclization into
thiophenones in the presence of an acid or a base or on
heating.
1
the compounds obtained were confirmed by IR, H and
1
3
C NMR, and MS data. As in the case of aryl deꢀ
1
3
rivatives 2a—j, the C NMR spectra of compounds
a—d show the coupling constant JC(3)—H(6) = 4.6 Hz,
5
which indicates (Z)ꢀconfiguration of the exocyclic
double bond.
Table 4. 13C NMR spectra (CDCl ) of the compounds synthesized
3
Comꢀ
pound
δ (J/Hz)
2
2
5
6
d
184.84 (d, C(3), J = 4.5); 169.32 (d, C(5), J = 3.2); 167.15 (qd, C(8), J = 3.9, J = 1.7); 146.11 (d, C(2), J = 2.2);
1
1
33.81 (s, Ph); 129.89 (dd, Ph, J = 168.5, J = 4.5); 128.40 (dd, Ph, J = 169.8, J = 4.8); 127.24 (d, Ph, J = 171.2);
14.69 (d, C(6), J = 172.0); 108.39 (d, C(4), J = 3.9); 66.38 (tt, OCH , J = 148.0, J = 4.5); 52.19 (t, OMe,
2
J = 147.4); 50.94 (tt, NCH , J = 148.0, J = 4.5)
2
j
184.46 (d, C(3), J = 4.6); 169.42 (d, C(5), J = 4.0); 166.84 (td, C(8), J = 2.9, J = 1.9); 146.18 (d, C(2), J = 2.2);
1
1
2
34.58 (s, Ph); 129.79 (dd, Ph, J = 169.2, J = 4.5); 128.17 (dd, Ph, J = 168.5, J = 4.5); 126.78 (d, Ph, J = 170.1);
14.18 (d, C(6), J = 171.3); 107.65 (d, C(4), J = 3.6); 61.03 (tq, OCH Me, J = 147.8, J = 4.6); 52.22 (tt, NCH );
2
2
5.83 (tt, CH ); 23.56 (t, CH , J = 147.5); 14.01 (qt, OCH CH , J = 127.2, J = 2.4)
2
2
2
3
d
d
183.54 (d, C(3), J = 5.0); 165.90 (d, C(5), J = 2.4); 172.04 (t, C(8), J = 3.5); 143.48 (d, C(2), J = 2.2);
1
5
1
16.19 (d, C(6), J = 172.2); 115.20 (s, CN); 79.16 (s, C(4)); 61.51 (tq, OCH Me, J = 148.1, J = 4.5);
2
3.68 (t, NCH ); 51.85 (t, NCH ); 26.13 (t, CH ); 25.83 (t, CH ); 23.11 (t, CH );
2
2
2
2
2
3.80 (qt, OCH CH J = 127.4, J = 2.6)
2
3
Major product (90%): 164.31 (dt, C(1), J = 3.2, J = 3.2); 163.34 (dt, C(4), J = 6.0, J = 3.0);
1
7
6
1
60.44 (br.s, C(5), W1/2 = 6); 142.96 (s, C(3)); 125.54 (d, C(2), J = 169.6); 118.06 (s, C(7));
5.82 (d, C(6), J = 169.4); 65.70 (tm, C(9), J = 144.4); 62.62 (tq, OCH CH , J = 148.5, J = 4.5);
2
3
1.29 (tq, OCH Me J = 148.6, J = 4.5); 49.63 (tm, C(8), J = 138.4); 13.94 (qt, OCH CH , J = 127.4, J = 2.6);
2
2
3
3.85 (qt, OCH CH , J = 127.4, J = 2.6)
2
3
Minor product (10%): 164.35 (C(1)); 163.52 (C(4)); 161.76 (C(5)); 143.61 (C(3)); 125.51 (C(2));
1
5
17.94 (s, C(7)); 71.28 (d, C(6), J = 177.4); 66.34 (tm, C(9), J = 145.2); 62.90 (OCH CH ); 61.37 (OCH Me);
2 3 2
1.01 (t, C(8), J = 145.2); 13.98 (CH ); 13.82 (CH )
3
3

Reactions of N,Nꢀ(dialkyl)arylthioacetamides
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 4, April, 2002
657
Experimental
Table 5. Selected bond lengths (d) in structure 2j
1H and 13C NMR spectra were recorded at 30 °C on
Bruker 250 (250.13 MHz for H) and Bruker DRXꢀ500 instruꢀ
Bond
d/Å
1
2
j (Xꢀray diffraction
Model
compound**
ments (500.13 and 125.13 MHz, respectively). IR spectra were
recorded on a IRꢀ75 spectrometer (in pellets with KBr). The
course of the reactions was monitored and the purity of the
products was checked by TLC on Silufol UVꢀ254 plates in
ethyl acetate—hexane (1 : 1), chloroform—ethanol (9 : 1), and
chloroform. Melting points are given noncorrected. Solvents
were purified and dried according to the standard procedures;
THF was preꢀdried over NaOH, distilled over Na, and kept
over 4A molecular sieves. The physicochemical characteristics
of the compounds obtained are given in Tables 1—3.
Synthesis of arylthioacetamides 1a—i (general procedure).
A mixture of the corresponding acetophenone (0.027 mol),
sulfur (1.3 g, 0.041 mol), and a cyclic amine (0.41 mol) was
refluxed for 20 h. The resulting dark brown mixture was cooled
and diluted with 100 mL of cold water. Trituration by a glass
rod gave a crystalline precipitate. Thioacetamide 1a—i was filꢀ
tered off and recrystallized from ethanol.
analysis)*
A
B
S(1)—C(5)
S(1)—C(2)
C(4)=C(5)
C(3)—C(4)
C(3)=O(7)
C(5)—N(19)
C(2)—C(3)
1.799(4)
1.736(4)
1.397(6)
1.425(6)
1.225(5)
1.323(6)
1.509(6)
1.793(4)
1.736(4)
1.380(6)
1.437(6)
1.227(5)
1.339(6)
1.504(6)
1.786
1.747
1.364
1.440
1.234
1.352
1.521
*
*
Two crystallographically independent molecules A and B.
* Calculated by the PM3/6ꢀ31G* method.
Synthesis of thiophenes (general procedure). Dimethyl
acetylenedicarboxylate (0.1 mol) was added to a solution of
N,Nꢀdialkylthioacetamide 1 or 4 (0.1 mol) in 10 mL of anꢀ
hydrous EtOH. The reaction mixture was refluxed for 2 h and
concentrated, and the precipitate that formed was triturated
with EtOH and filtered off. The product was recrystallized
from a chloroform—hexane mixture.
Synthesis of cyanothioacetamides 4a—c (general procedure).
Finely divided P S (1.0 g) was added to a stirred suspension of
2
5
the corresponding cyanoacetamide (2.0 g) in 100 mL of THF.
The reaction mixture was heated at 50 °C for 30 min, cooled,
and concentrated at a reduced pressure. Water (100 mL) was
added, and the cyanothioacetamide obtained was recrystallized
with coal and dried over P O .
Xꢀray diffraction analysis of compound 2j was carried out on
a Bruker P4 diffractometer (MoꢀKα radiation, graphite monoꢀ
chromator, θ/2θ scan mode, 2θ < 50°). Bright red crystals are
monoclinic: a = 11.175(2) Å, b = 11.512(2) Å, c = 28.101(5) Å,
2
5
3
C(22)
β = 95.726(8)°, V = 3597.2(10) Å , space group Cc,
C19H21NO S, Z = 8, molecular mass 343.43, d =
C(15)
3
–3
calc
C(23)
–1
1
.268 g cm , µ = 0.196 mm . The intensities of 3350 indeꢀ
pendent reflections were measured for a crystal 0.1×1.2×1.4 mm
in size; corrections for crystal habit absorption were applied
C(21)
C(20)
C(14)
C(13)
C(24)
N(19)
C(16)
C(17)
(
transmission 0.84—0.97). The structure was solved by the diꢀ
rect method using the SHELXSꢀ97 program and refined by the
leastꢀsquares method in the anisotropicꢀisotropic approximaꢀ
C(4)
C(5)
S(1)
C(18)
tion using the SHELXLꢀ97 program to wR = 0.1303; S = 1.026
2
for all reflections (R = 0.0456 for 2974 F > 4σ). Hydrogen
atoms were located geometrically and refined isotropically with
the fixed carbon atoms which they are bonded to. Strucꢀ
ture 2j is displayed in Fig. 1. Selected bond lengths are given in
Table 5.
O(7)
C(3)
C(6)
C(2)
O(10)
This work was financially supported by the Russian
Foundation for Basic Research (Project Nos. 99ꢀ07ꢀ90133
and 01ꢀ03ꢀ96431). The authors are grateful to the
RFBR for access to the Cambridge Crystallographic
Database.
C(8)
O(9)
C(11)
References
C(12)
1
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Fig. 1. Structure of one of the two crystallographically indeꢀ
pendent molecules of compound 2j (according to the Xꢀray
diffraction data).
2. V. S. Berseneva, Yu. Yu. Morzherin, W. Dehaen, I. Luyten,
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4
5
6
7
8
Received September 3, 2001;
in revised form December 21, 2001