Novel N,S- and S,S-substituted dienes synthesized from mercapto triazole and some amine derivatives

Article abstract of DOI:10.1080/10426500701196499

2-Nitrodiene 1 reacted with 3-mercapto-1,2,4-triazole and cyclohexyl thiol to yield compounds 3 and 4, respectively. Compounds 7a-d were obtained by reactions of 6a-d with 2. The novel N,S-substituted dienes 9a-c were obtained by treatment of compound 6b

Full text of DOI:10.1080/10426500701196499

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Novel N,S- and S,S-Substituted
Dienes Synthesized from
Mercapto Triazole and Some
Amine Derivatives
Cemil Ibis a & Gökşin Aydinli a
a Faculty of Engineering, Department of Chemistry ,
Istanbul University , Avcilar, Istanbul, Turkey
Published online: 07 Jun 2007.
To cite this article: Cemil Ibis & Gökşin Aydinli (2007) Novel N,S- and S,S-
Substituted Dienes Synthesized from Mercapto Triazole and Some Amine Derivatives,
Phosphorus, Sulfur, and Silicon and the Related Elements, 182:7, 1427-1436, DOI:
10.1080/10426500701196499
To link to this article: http://dx.doi.org/10.1080/10426500701196499
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Phosphorus, Sulfur, and Silicon, 182:1427–1436, 2007
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701196499
Novel N, S- and S, S-Substituted Dienes Synthesized
from Mercapto Triazole and Some Amine Derivatives
Cemil Ibis
¨
Goks¸in Aydınlı
Istanbul University, Faculty of Engineering, Department of Chemistry,
Avcılar, Istanbul, Turkey
2-Nitrodiene 1 reacted with 3-mercapto-1,2,4-triazole and cyclohexyl thiol to yield
compounds 3 and4, respectively. Compounds 7a–d were obtained by reactions of
6a–d with 2. The novel N,S-substituted dienes 9a–c were obtained by treatment
of compound 6b with the piperazine derivatives 8a–c. Compound 6b was reacted
with 10 to give compound 11 as a new morpholine derivative. Compound 6b gave
a new monobutadienyl homopiperazine 13 when reacted with homopiperazine in
methylene chloride. Compound 4 was structurally characterized by single-crystal
X-ray diffraction.
Keywords Mono(thio)substituted nitrodiene; 2-nitrohalodiene; 3-mercapto-1,2,4-
triazole; morpholine; piperazine; N, S-substituted nitrodiene
INTRODUCTION
The synthesis of unsaturated thio-substituted halogenated organic
compounds from the reaction of various halogenated alkenes and di-
enes with a number of thiols were published.1−8It is known that
N, S−substituted butadienes were prepared from the reaction of
mono(thio)substituted compounds with amines (primary amines, piper-
azine, morpholine, piperidine, etc).9−16 There are many studies about
the reactions of some N-nucleophiles, such as benzotriazol, 3,5-
dimethylpyrazole, and indol with nitrodienes.17−19 Triazoles, and in
particular the 1,2,4-triazole ring, have been incorporated into a wide
variety of therapeutically interesting drug candidates, including anti-
inflammatory, sedatives, antianxiety, and antimicrobial agents.20−28
Some piperazine and piperidine compounds have also been subject to
Received July 27, 2005; accepted December 4, 2006.
We thank the Research Fund of the University of Istanbul for financial support of this
work.
Address correspondence to Cemil Ibis, Istanbul Universitesi, Muhendislik Fakultesi,
Kimaya Bolumu, Avcilar, Istanbul 34320, Turkey. E-mail: ibiscml@istanbul.edu.tr
1427

1428
C. Ibis and G. Aydınlı
medicinal applications and gen transfer studies due to their interesting
biological activity and chemical effects.29−31
In this article, we synthesized and characterized new N, S-and S, S-
substituted nitrobutadienes. Reaction of mono(thio)substituted diene
compounds with some amines and triazoles provided the corresponding
N, S-substituted halodiene derivatives.
RESULTS AND DISCUSSION
The position adjacent to =C(NO2)- is the most favorable for nucleophilic
attack in the halonitrovinyl moiety. Polychlorinated nitrodienes are
highly electrophilic compounds. The quantum-chemical analysis shows
that halonitrodienes must be active in processes of nucleophilic vinylic
substitution.32−38
Reaction of 1 with the thiols 2 and 5d resulted in the formation of the
new butadienes 3 and 4. The S, S-disubstituted nitrobutadiene 4 was
obtained as a by-product in the synthesis of 6d using the standard work
up procedure (see Experimental Section). The mono(thio)substituted
dienes 6a–d29,13,39,7 react with 3-mercapto-1,2,4-triazole to give the new
derivatives 7a–d. Compound 6b reacts with the piperazines 8a–c to
give the N, S-substituted butadienes 9a–c. Treatment of 6b with the
amines 10 and 12 results in the formation of the substitution products
11 and 13, respectively (Scheme 1).
The structures of the new compounds were established by their spec-
troscopic data. In the IR spectra the >NH groups of the triazole rings40
showed characteristic bands in the range of 3100-3300 cm−1. In the
case of compounds 11 and 13, characteristic NH bands at 3400 and
3450 cm−1 were observed. The presence of the OH-group in compound
9c is revealed by a characteristic band at 3350 cm−1
.
The stereochemistry of the butadiene 4 was confirmed by the result
of a single crystal X-ray structure determination. Experimental details
for data collection and structure refinement are summarized in Table I.
An ORTEP diagram of the molecular structure of 4 in the crystal with
atom numbering scheme is shown in Figure 1. Selected bond lengths
and angles can be found in Table II. Physical properties and spectro-
scopic data of the synthesized compounds are listed in Table III and
Table IV.
The C-C bond lengths of the butadiene chain in 4 are 1.332(8),
˚
1.482(9), and 1.343(6) A for C(2)-C(1), C(3)-C(2), and C(4)-C(3), respec-
tively. The bond angles C(1)-C(2)-C(3) and C(2)-C(3)-C(4) are 123.3(6)◦
and 126.0(4)◦, respectively. The diene system is not planar. The torsion
angle C(4)-C(3)-C(2)-C(1) is 106.3(7)◦.

N, S- and S, S-Substituted Chlorobutadienes
1429
SCHEME 1
EXPERIMENTAL
Melting points were determined on a Buchi B-540 capillary apparatus
and were uncorrected. Elemental analyses were carried out on a Carlo
Erba 1110 analyzer. Infrared spectra were recorded on a Shimadzu

1430
C. Ibis and G. Aydınlı
TABLE I Crystallographic Data and Structure
Refinement for Compound 4
Sum formula
fw (g.mol−1
(C16H22NO2Cl3S2 )
430.83
)
Crystal dimensions (mm)
Crystal system
Space group
0.60 × 0.40 × 0.20
monoclinic
P21/n
Lattice parameters
˚
a (A)
12.0862(12)
11.1625(8)
16.337(1)
90
110.840(4)
90
2059.9(3)
4
1.338
˚
b (A)
˚
c (A)
α (◦)
β (◦)
γ (◦)
3
˚
Vol [A ]
Z
Dcalc(g.cm−3
)
μ [cm−1
F(000)
]
6.49
864.00
Index ranges
−14 ≤ h ≤ 14
−13 ≤ k ≤ 13
−19 ≤ l ≤ 19
66140
Reflections collected
Independent reflections
Data/restraints/parameters
Goodness-of-fit on F2
3579[Rint= 0.059]
1717/0/239
0.752
Final R indices [I>3 σ (I)]
Largest diff. peak and hole
R = 0.074, wR = 0.015
−3
˚
0.40 and −0.41 e. A
R = ꢀ ꢀFo| – |Fcꢀ/ꢀ |Fo|, Rw = [ꢀ w (|Fo| – |Fc|)2/ꢀw Fo2]1/2
1
FTIR-8101 spectrometer in KBr discs. H and 13C NMR spectra were
measured on VarianUNITY INOVA spectrometer. Mass spectra were ob-
tained using Finnigan LCQ Advantage Max. LC/MS. Thin-layer chro-
matography was performed on 0.5 mm × 20 cm × 20 cm E. Merck sil-
ica gel plates (60 F-254). Column chromatography was conducted over
Silica gel (63–200 μm), available from E. Merck. All chemicals were
reagent grade and used without further purification. Moisture was ex-
cluded from the glass apparatus using CaCl2 drying tubes.
Preparation of Compounds 4 and 6d. General Procedure
To 2 g of 1,1,3,4,4-pentachloro-2-nitro-1,3-butadiene 1 was added an
equimolar amount of the thiol 5d and the mixture was vigorously stirred
without solvent at room temperature until completion of the reaction.
Stirring of the mixture was continued for 36 h. Then, chloroform was

N, S- and S, S-Substituted Chlorobutadienes
1431
FIGURE 1 ORTEP view of the molecular structure of 4 in the crystal; dis-
placement ellipsoids are drawn at the 30% probability level.
added to the reaction mixture. The organic layer was separated, washed
with water several times, and dried over anhydrous CaCl2 or MgSO4.
After removal of the solvent, a mixture containing the compounds 4
and 6d was obtained. The pure compounds 4 and 6d were seperated by
column chromatography over silica gel using petroleum ether as eluent.
Preparation of Compounds 3 and 7a–d, General Procedure
To a solution of 0.5 g of 1 or 6a–d in 10 mL of ethanol was added an
equimolar amount of 2 in 20 mL of ethanol and the reaction mixture
was vigorously stirred at room temperature until completion of the re-
action. Stirring of the reaction mixture was continued for 4 h. Then,
chloroform was added to the reaction mixture. The organic layer was
separated and washed with water several times and dried over anhy-
drous CaCl2 or MgSO4. After removal of the solvent, the products were
either crystallized or purified by column chromatography over silica gel.
Preparation of Compounds 9a–c, 11 and 13, General Procedure
To a solution of 0.2 g of 6b in 10 mL of dichloromethane was added an
equimolar amount of the respective amine in 20 mL of dichloromethane

1432
C. Ibis and G. Aydınlı
◦
˚
TABLE II Selected Bond Lengths [A] and Angles [ ] for
Compound 4
Cl(3)
Cl(2)
S(2)
C(2)
C(1)
C(11)
C(5)
N(1)
C(3)
C(2)
C(6)
C(13)
C(16)
C(11)
C(8)
C(8)
1.723(7)
1.711(6)
1.831(6)
1.827(6)
1.230(7)
1.343(6)
1.332(8)
1.490(1)
1.510(1)
1.570(1)
1.470(1)
1.520(1)
1.480(1)
Cl(1)
S(2)
S(1)
O(1)
N(1)
C(3)
C(1)
C(4)
C(4)
N(1)
C(3)
C(2)
C(10)
C(11)
C(9)
C(14)
C(6)
C(13)
1.699(7)
1.739(6)
1.776(5)
1.214(9)
1.454(6)
1.482(9)
1.540(7)
1.520(1)
1.540(1)
1.490(1)
1.520(1)
1.490(1)
S(1)
O(2)
C(4)
C(1)
C(5)
C(12)
C(15)
C(16)
C(7)
C(9)
C(4)
C(3)
O(1)
C(3)
C(2)
N(1)
C(2)
Cl(3)
C(3)
C(5)
C(12)
C(10)
C(15)
C(7)
C(14)
S(2)
N(1)
N(1)
C(4)
C(3)
C(3)
C(1)
C(2)
C(2)
C(11) 106.1(3) C(4)
S(1)
N(1)
C(4)
C(4)
C(3)
C(1)
C(1)
C(2)
C(5)
100.4(2)
117.4(5)
124.0(4)
120.7(3)
126.0(4)
122.1(5)
115.3(3)
121.1(5)
110.6(5)
112.2(4)
109.3(6)
O(1)
O(2)
S(1)
N(1)
C(4)
Cl(2)
C(3)
C(1)
S(1)
119.3(4) C(3)
123.3(5) C(3)
115.3(4) S(2)
113.5(4) C(2)
120.3(5) C(2)
122.6(6) Cl(1)
115.5(4) Cl(3)
O(2)
S(2)
S(1)
C(4)
Cl(1)
Cl(2)
C(1)
C(6)
S(1)
123.3(6) C(10) C(5)
106.4(4) C(6) C(5)
C(10) C(5)
C(11) C(12) C(13) 110.3(6) C(9)
C(10) C(5)
C(16) C(15) C(14) 109.2(9) C(11) C(16) C(15) 111.4(6)
C(6)
S(2)
C(7)
C(8)
111.7(9) C(13) C(14) C(15) 113.5(7)
C(11) C(16) 113.4(4)
C(11) C(12) 105.7(5) S(2)
C(12) C(11) C(16) 112.4(6) C(8)
C(5) C(6) C(7) 111.5(6) C(7)
C(12) C(13) C(14) 110.8(6)
C(9)
C(8)
C(10) 111.5(6)
C(9) 111.9(7)
and the reaction mixture was vigorously stirred at room temperature
until completion of the reaction. Stirring of the reaction mixture was
continued for 4 h. Then, chloroform was added to the reaction mixture.
The organic layer was separated, washed with water several times, and
dried over anhydrous CaCl2 or MgSO4. After removal of the solvent, the
products were either crystallized or purified by column chromatography
over silica gel.
X-Ray Diffraction
Suitable single crystals of 4 were obtained by slow evaporation of a chlo-
roform solution. A single crystal of 4 was mounted on an Rigaku R-Axis
Rapid-S diffractometer equipped with a graphite monochromatized

1433

1434
C. Ibis and G. Aydınlı
TABLE IV 1H and 13C NMR Data of the New Compounds
1H/13C-NMR δ (ppm)
3
4
1H (DMSO-d6)
1H (CDCl3)
8.57 (s, 2H, CH), 8.67 (s, 2H, NH)
1.18–2.01 (m, 20H, CH2), 3.24–3.47 (m, 2H, SCH)
25.5, 25.6, 26.3, 33.8, 49.5, 51.3, 123.2, 128.0, 142.9, 157.1
0.71–0.97 (m, 3H, CH3), 1.12–1.80 (m, 12H, (CH2)6), 2.51–3.03
(m, 2H, SCH2), 8.74 (s, 1H, CH), 8.80 (s, 1H, NH)
0.73–0.98 (m, 3H, CH3), 0.98–2.09 (m, 16H, (CH2)8), 2.50–2.68
(m, 2H, SCH2), 8.55 (s, 1H, CH), 9.53 (s, 1H, NH)
0.84–1.24 (m, 3H, CH3), 1.26–1.60 (m, 28H, (CH2)14), 2.92–3.32
(m, 2H, SCH2), 8.75 (s, 1H, CH), 8.81 (s, 1H, NH)
1.20–2.50 (m, 11H, C6H11), 8.77 (s, 1H, CH), 8.83 (s, 1H, NH)
0.82–0.90 (m, 3H, CH3), 1.24–1.67 (m, 16H, (CH2)8), 1.69–1.78
(m, 3H, OCH3), 2.91–3.05 (m, 2H, SCH2), 3.26–3.91 (m, 8H,
NCH2), 6.89–7.24 (m, 4H, arom–H)
9.6, 18.1, 24.2, 24.5, 24.7, 24.9, 25.0, 25.3, 25.5, 27.3, 31.0, 31.6,
33.0, 45.9, 48.8, 51.1, 107.3, 113.6, 116.7, 120.1, 122.4, 147.8
0.81 (t, J = 6.8 Hz, 3H, CH3), 1.19–1.73 (m, 16H, (CH2)8), 2.91
(t, J = 7.3 Hz, 2H, SCH2), 3.17–3.75 (m, 8H, NCH2)
6.85–7.19 (m, 4H, arom-H)
13C (CDCl3)
1H (DMSO-d6)
7a
7b
7c
1H (DMSO-d6)
1H (DMSO-d6)
7d 1H (DMSO-d6)
9a
1H (CDCl3)
13C (CDCl3)
1H (CDCl3)
9b
13C (CDCl3)
1H (CDCl3)
14.3, 22.9, 28.9, 29.5, 29.6, 29.7, 30.0, 32.1, 35.8, 39.5, 44.0,
47.8, 50.6, 53.6, 116.7, 119.6, 119.8, 124.4, 125.0, 127.1,
138.8, 155.0, 157.0, 169.7
0.86 (t, J = 6.8 Hz, 3H, CH3), 1.24–1.68 (m, 16H, (CH2)8), 2.95
(t, J = 7.3 Hz, 2H, SCH2), 3.17–3.78 (m, 8H, NCH2), 6.76
(d, J = 8.8 Hz, 2H, arom-H), 6.85 (d, J = 8.8 Hz, 2H, arom-H)
14.3, 22.9, 28.9, 29.3, 29.5, 29.6, 29.7, 30.0, 32.1, 35.8, 51.3,
53.5, 116.4, 118.5, 119.6, 123.8, 125.0, 127.0
0.85 (t, J = 6.8 Hz, 3H, CH3), 1.24–1.67 (m, 20H, (CH2)8 and
NCH2), 2.62–2.67 (m, 2H, SCH2), 2.89–4.07 (m, 8H,
morpholine-CH2)
0.81–1.08 (m, 3H, CH3), 1.12–1.76 (m, 16H, (CH2)8), 2.42–2.74
(m, 2H, SCH2), 2.81–4.27 (m, 10H, CH2)
9c
13C (CDCl3)
1H (CDCl3)
11
13
1H (CDCl3)
13C (CDCl3)
14.3, 22.9, 24.7, 28.2, 29.6, 32.1, 36.6, 39.5, 46.2, 50.8, 54.8,
66.9, 70.5, 118.7, 125.4, 126.7, 162.2, 171.9
˚
MoKα radiation source (λ = 0.71073 A). The structure was solved by
SIR 92 41 and refined with CRYSTALS.42 The positions of the H atoms
˚
bonded to C atoms were calculated (C H distance 0.96 A), and refined
using a riding model. The H atom displacement parameters were re-
stricted to be 1.2Ueq of the parent atom. All calculations were performed
using the Crystal Structure Analysis software package.43 An ORTEP-
III view of the molecular structure of 4 is given in Figure 1.44 Crystallo-
graphic data (excluding structure factors) for the structure reported in

N, S- and S, S-Substituted Chlorobutadienes
1435
this article have been deposited with the Cambridge Crystallographic
Data Centre as supplementary publication No. CCDC 278799.45
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