Functionalization of highly electrophilic N-(2,2,2-Trichloroethylidene)- and N-(2,2-Dichloro-2-phenylethylidene) arenesulfonamides with dithiooxamide

Article abstract of DOI:10.1134/S1070428012040021

Depending on the reactant ratio, dithiooxamide (ethanedithioamide) reacted as N-nucleophile or N,N'-binucleophile with highly electrophilic aldimines, N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2- phenylethylidene) arenesulfonamides, to give the c

Full text of DOI:10.1134/S1070428012040021

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2012, Vol. 48, No. 4, pp. 481–484. © Pleiades Publishing, Ltd., 2012.
Original Russian Text © G.N. Rozentsveig, A.I. Fedotova, V.Yu. Serykh, K.A. Chernyshev, I. B. Rozentsveig, 2012, published in Zhurnal Organicheskoi
Khimii, 2012, Vol. 48, No. 4, pp. 483–486.
Functionalization of Highly Electrophilic
N-(2,2,2-Trichloroethylidene)- and N-(2,2-Dichloro-2-phenyl-
ethylidene)arenesulfonamides with Dithiooxamide
G. N. Rozentsveig, A. I. Fedotova, V. Yu. Serykh, K. A. Chernyshev, and I. B. Rozentsveig
Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: i_roz@irioch.irk.ru
Received December 25, 2011
Abstract—Depending on the reactant ratio, dithiooxamide (ethanedithioamide) reacted as N-nucleophile or
N,N′-binucleophile with highly electrophilic aldimines, N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-
phenylethylidene)arenesulfonamides, to give the corresponding mono- or bis-adducts, N-[2-polychloro-1-(aryl-
sulfonylamino)ethyl]ethanedithioamides or N,N′-bis[2-polychloro-1-(arylsulfonylamino)ethyl]ethanedithio-
amides, in good yield.
DOI: 10.1134/S1070428012040021
Reactions of highly electrophilic N-sulfonyl poly-
chloroaldehyde imines with oxygen-, nitrogen-, sulfur-,
and carbon-centered nucleophiles underlie prepara-
tively efficient approaches to a broad series of N-poly-
haloalkyl sulfonamides. The latter possess various
functional groups, including reactive NH group and
polyhalomethyl fragments, and are used in the syn-
thesis of difficultly accessible acyclic and heterocyclic
sulfonamides [1–7]. We previously showed [8] that
addition of thioamides to N-(polychloroethylidene)-
arenesulfonamides leads to the formation of polyfunc-
tional adducts capable of undergoing cyclization to
difficultly accessible 4-sulfonylaminothiazoles [6, 7].
In continuation of these studies, in the present work we
examined reactions of N-(2,2,2-trichloroethylidene)-
and N-(2,2-dichloro-2-phenylethylidene)arenesulfon-
amides I and II with dithiooxamide with a view to
develop methods for the preparation of functionalized
N-haloalkyl amides as substrates for subsequent
heterocyclization and biological screening.
Dithiooxamide derivatives attract interest as start-
ing compounds for the synthesis of a number of S,N-
heterocycles [9, 10]. In addition, dithiooxamide and its
derivatives are used as ligands to obtain metal com-
plexes [11–13] and catalysts in asymmetric syntheses
[11], as well as in the preparation of inorganic nano-
tubes [13]. Structural studies on dithiooxamide and
its derivatives performed by spectral and quantum-
chemical methods [14–16] are important from the
theoretical viewpoint.
Scheme 1.
CCl2X S
ArSO2
NH2
N
N
H
1 : 1
H
S
Cl
S
DMF, 100°C
IIIa–IIIc, IVa–IVc, 68–95%
NH2
N
Cl
X
+
H2N
Ar
CCl2X S
H
S
Ia–Ic, IIa–IIc
H
N
ArSO2
N
N
N
SO2Ar
2 : 1
H
H
S
CCl2X
Va–Vc, VIa, VIb, 70–85%
I, III, V, X = Cl; II, IV, VI, X = Ph; Ar = Ph (a), 4-MeC6H4 (b), 4-ClC6H4 (c).
481

ROZENTSVEIG et al.
482
Initial N-sulfonyl imines I and II are readily
intensities of all signals conformed to the assumed
structure.
available via previously developed procedure which is
based on radical addition of trichloroethylene and
phenylacetylene to N,N-dichloroarenesulfonamides
[1, 17, 18]. In reactions with imines I and II dithio-
oxamide acts as nitrogen-centered nucleophile which
adds at the activated C=N bond. The reactions
occurred most effectively on heating in dimethylform-
amide which ensured homogeneous process at a re-
quired temperature and the best yield of compounds
III–VI. However, heating of the reaction mixture
above 120°C resulted in reduced yield of adducts III–
VI because of tarring.
The reaction with equimolar amounts of the reac-
tants selectively involved only one NH2 group of
dithiooxamide with formation of the corresponding
monoadducts, N-[2-polychloro-1-(arylsulfonylamino)-
ethyl]ethanedithioamides IIIa–IIIc and IVa–IVc, in
good yield. When 2 equiv of imine I or II was used,
we obtained N,N′-bis[2-polychloro-1-(arylsulfonyl-
amino)ethyl]ethanedithioamides Va–Vc, VIa, and VIb
as a result of addition at both NH2 groups of dithio-
oxamide. Neither S- nor N,S-addition products were
formed.
The above reactions required a fairly long time (up
to 15 h), i.e., dithioxamide is less reactive toward
imines I and II as compared to thiourea and thioacet-
amide [8] which reacted with the same substrates at
a higher rate. Presumably, the reactivity of dithioox-
amide is reduced due to mutual electron-withdrawing
effect of two thioamide groups. N-(Trichloroethyli-
dene) derivatives I turned out to be more reactive than
N-(2,2-dichloro-2-phenylethylidene) analogs II, which
is consistent with stronger electron-acceptor effect of
trichloromethyl group compared to dichloro(phenyl)-
methyl. No appreciable effect of the substituent in the
benzene ring was observed.
To conclude, we have found conditions ensuring
selective addition of ethanedithioamide at the C=N
bond of N-(2,2,2-trichloroethylidene)- and N-(2,2-di-
chloro-2-phenylethylidene)arenesulfonamides. Newly
synthesized N-polychloroalkyl sulfonamides III–VI
possess pharmacophoric arenesulfonamide and ethane-
dithioamide fragments. They may be promising as
ligands and intermediate products for the synthesis of
thiazole derivatives, taking into account the presence
in their molecules of RSO2NH, NHC(S), and C–Cl
moieties which can be involved in subsequent hetero-
cyclization.
EXPERIMENTAL
1
The H and 13C NMR spectra were recorded on
a Bruker DPX-400 spectrometer at 400.61 and
100.13 MHz, respectively, using TMS as internal refer-
ence. The IR spectra were measured on a Bruker IFS-
25 spectrometer from samples pelleted with KBr.
N-[2,2,2-Trichloro-1-(phenylsulfonylamino)-
ethyl]ethanedithioamide (IIIa). A solution of 1.44 g
(0.005 mol) of compound Ia and 0.60 g (0.005 mol) of
ethanedithioamide in 5 ml of DMF was stirred for 12 h
at 90–100°C. The mixture was cooled and diluted with
150 ml of water, the precipitate was filtered off and
dissolved in 100 ml of acetone, the solution was
filtered, and the filtrate was poured into 100 ml of
water. The precipitate was filtered off, washed with
50 ml of diethyl ether on a filter, and dried under
reduced pressure. Yield 1.65 g (81%), mp 130–132°C.
IR spectrum, ν, cm–1: 3427, 3321, 3243, 3148 (NH),
1
1610, 1341, 1166 (SO2). H NMR spectrum
3
(DMSO-d6), δ, ppm: 6.47 d.d (1H, CH, J = 9.6,
9.8 Hz); 7.48 m, 7.59 m, and 7.79 m (5H, C6H5),
3
9.53 d (1H, SO2NH, J = 9.6 Hz), 9.59 br.s and
Compounds III–VI were isolated as orange
powders which were soluble in DMSO, DMF, and
aqueous alkali, poorly soluble in acetone, and insol-
uble in water. The structure of III–VI was unambigu-
ously proved by their IR and NMR spectra and ele-
mental analyses. Protons in the NH–CH–NH fragment
3
10.61 br.s (1H each, NH2), 10.57 d [1H, NHC(S), J =
9.8 Hz]. 13C NMR spectrum (DMSO-d6), δC, ppm:
74.24 (CH), 99.51 (CCl3); 126.78, 129.12, 133.07,
140.16 (C6H5); 188.01 (H2NC=S), 188.42 (NHC=S).
Found, %: C 29.41; H 2.39; Cl 26.01; N 10.14;
S 23.48. C10H10Cl3N3O2S3. Calculated, %: C 29.53;
H 2.48; Cl 26.15; N 10.33; S 23.65.
1
characteristically appeared in the H NMR spectra as
three groups of signals: a doublet of doublets at
δ 6.21–6.50 ppm (CH) and two downfield doublets
(NH) with a coupling constant of 9.2–9.8 Hz. The
spectra of monoadducts III and IV contained a broad-
ened singlet from the NH2 group, whereas no such
signal was present in the spectra of bis-adducts V and
VI. Signals from aromatic protons were also observed
Compounds IIIb and IIIc were synthesized in
a similar way.
N-[2,2,2-Trichloro-1-(4-chlorophenylsulfonyl-
amino)ethyl]ethanedithioamide (IIIb) was synthe-
sized from 1.61 g (0.005 mol) of Ib. Yield 1.69 g
(77%), mp 134–136°C. IR spectrum, ν, cm–1: 3367,
3294, 3214, 3140 (NH), 1658, 1349, 1168 (SO2).
1
in the H NMR spectra of III–VI, and the relative
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FUNCTIONALIZATION OF HIGHLY ELECTROPHILIC N-(2,2,2-TRICHLOROETHYLIDENE)-
483
3
1H NMR spectrum (DMSO-d6), δ, ppm: 6.46 d.d (1H,
spectrum (DMSO-d6), δ, ppm: 6.50 d.d (1H, CH, J =
3
CH, J = 9.6, 9.8 Hz), 7.44 and 7.72 (4H, C6H4,
9.6, 9.8 Hz), 7.42 m and 7.67 m (5H, C6H5), 7.48 and
3
3
AA′BB′), 9.58 d (1H, SO2NH, J = 9.6 Hz), 9.62 br.s
7.69 (4H, C6H4, AA′BB′), 9.21 d (1H, SO2NH, J =
and 10.65 br.s (1H each, NH2), 10.58 d [1H, NHC(S),
3J = 9.8 Hz]. 13C NMR spectrum (DMSO-d6), δC, ppm:
74.04 (CH), 99.00 (CCl3); 128.88, 129.17, 138.19,
138.50 (C6H4); 185.40 (H2NC=S), 186.77 (HNC=S).
Found, %: C 27.35; H 2.15; Cl 31.65; N 9.37; S 21.97.
C10H9Cl4N3O2S3. Calculated, %: C 27.22; H 2.06;
Cl 32.14; N 9.52; S 21.80.
9.8 Hz), 9.48 br.s and 10.61 br.s (1H each, NH2),
10.46 d (1H, NHC=S, 3J = 9.6 Hz). 13C NMR spectrum
(DMSO-d6), δC, ppm: 72.7 (CH), 93.6 (CCl2); 127.4,
128.3, 129.9, 139.1 (C6H5); 128.7, 128.9, 137.2, 137.7
(C6H4); 186.9 (H2NC=S), 187.6 (HNC=S). Found, %:
C 39.74; H 2.86; Cl 21.90; N 8.56; S 19.88.
C16H14Cl3N3O2S3. Calculated, %: C 39.80; H 2.92;
Cl 22.03; N 8.70; S 19.92.
N-[2,2,2-Trichloro-1-(4-methylphenylsulfonyl-
amino)ethyl]ethanedithioamide (IIIc) was synthe-
sized from 1.51 g (0.005 mol) of Ic. Yield 1.42 g
(68%), mp 140–142°C. IR spectrum, ν, cm–1: 3360,
3294, 3250, 3162 (NH), 2945, 2921 (C–Halk), 1595,
N-[2,2-Dichloro-1-(4-methylphenylsulfonyl-
amino)-2-phenylethyl]ethanedithioamide (IVc) was
synthesized from 1.71 g (0.005 mol) of IIc. Yield
2.03 g (88%), mp 143–145°C. IR spectrum, ν, cm–1:
1
1
1338, 1166 (SO2). H NMR spectrum (DMSO-d6), δ,
3242 (NH), 1596, 1328, 1163 (SO2). H NMR spec-
3
ppm: 2.23 s (3H, CH3), 6.46 d.d (1H, CH, J = 9.4,
trum (DMSO-d6), δ, ppm: 2.26 s (3H, CH3), 6.48 d.d
3
9.6 Hz), 7.18 and 7.56 (4H, C6H4, AA′BB′), 9.55 d (1H,
(1H, CH, J = 9.2, 9.6 Hz), 7.14 and 7.52 (4H, C6H4,
3
SO2NH, J = 9.4 Hz), 9.60 br.s and 10.64 br.s (1H
AA′BB′), 7.48 m and 7.67 m (5H, C6H5), 9.44 d (1H,
3
3
each, NH2), 10.59 d (1H, NHC=S, J = 9.6 Hz).
SO2NH, J = 9.2 Hz), 9.47 br.s and 10.60 br.s
3
13C NMR spectrum (DMSO-d6), δC, ppm: 21.1 (CH3),
74.3 (CH), 99.4 (CCl3); 126.2, 129.2, 135.8, 143.5
(C6H4); 187.7 (H2NC=S), 188.2 (HNC=S). Found, %:
C 31.47; H 2.71; Cl 25.43; N 9.67; S 22.98.
C11H12Cl3N3O2S3. Calculated, %: C 31.40; H 2.87;
Cl 25.28; N 9.99; S 22.86.
(1H each, NH2), 10.54 d (1H, NHC=S, J = 9.6 Hz).
13C NMR spectrum (DMSO-d6), δC, ppm: 21.5 (CH3),
72.6 (CH), 93.7 (CCl2); 126.8, 128.9, 136.1, 144.1
(C6H4); 127.4, 128.5, 129.8, 139.1 (C6H5); 187.0
(H2NC=S), 187.4 (HNC=S). Found, %: C 44.08; H 3.65;
Cl 15.17; N 8.94; S 20.68. C17H17Cl2N3O2S3. Calculat-
ed, %: C 44.15; H 3.71; Cl 15.33; N 9.09; S 20.8.
N-[2,2-Dichloro-2-phenyl-1-(phenylsulfonyl-
amino)ethyl]ethanedithioamide (IVa). A solution of
1.64 g (0.005 mol) of imine IIa and 0.60 g (0.005 mol)
of ethanedithioamide in 5 ml of DMF was stirred for
15 h at 100°C, and the mixture was then treated as
described above for IIIa. Yield 1.74 g (78%), mp 100–
102°C. IR spectrum, ν, cm–1: 3285, 3123 (NH), 1649,
Compounds Va– Vc were synthesized as described
above for IIIa–IIIc using 2 equiv of imines Ia–Ic.
N,N′-Bis[2,2,2-trichloro-1-(phenylsulfonyl-
amino)ethyl]ethanedithioamide (Va) was synthesized
from 1.44 g (0.005 mol) of Ia and 0.30 g (0.0025 mol)
of ethanedithioamide. Yield 1.32 g (76%), mp 128–
130°C. IR spectrum, ν, cm–1: 3358, 3261 (NH), 1598,
1
1342, 1169 (SO2). H NMR spectrum (DMSO-d6), δ,
3
1
ppm: 6.47 d.d (1H, CH, J = 9.4, 9.7 Hz); 7.47 m,
1306, 1161 (SO2). H NMR spectrum (DMSO-d6), δ,
3
7.59 m, 7.60 m, and 7.79 m (10H, C6H5); 9.54 d (1H,
ppm: 6.36 d.d (2H, CH, J = 9.4, 9.6 Hz); 7.48 m,
3
SO2NH, J = 9.7 Hz), 9.57 br.s and 10.08 br.s (1H
7.58 m, and 7.77 m (10H, C6H5); 9.34 d (2H, SO2NH,
3
3
3J = 9.4 Hz), 10.12 d (2H, NHC=S, J = 9.6 Hz).
each, NH2), 10.56 d (1H, NHC=S, J = 9.4 Hz).
13C NMR spectrum (DMSO-d6), δC, ppm: 72.5 (CH),
93.8 (CCl2); 125.1, 127.4, 128.1, 128.6, 130.0, 132.1,
138.9, 139.2 (C6H5); 186.9 (H2NC=S), 187.6 (HNC=S).
Found, %: C 42.69; H 3.22; Cl 15.73; N 9.21; S 21.38.
C16H15Cl2N3O2S3. Calculated, %: C 42.86; H 3.37;
Cl 15.81; N 9.37; S 21.45.
13C NMR spectrum (DMSO-d6), δC, ppm: 74.2 (CH),
99.4 (CCl3); 125.2, 128.7, 132.6, 139.4 (C6H5); 184.9
(C=S). Found, %: C 31.06; H 2.19; Cl 30.53; N 8.03;
S 18.33. C18H16Cl6N4O4S4. Calculated, %: C 31.18;
H 2.33; Cl 30.68; N 8.08; S 18.50.
N,N′-Bis[2,2,2-trichloro-1-(4-chlorophenylsul-
fonylamino)ethyl]ethanedithioamide (Vb) was syn-
thesized from 1.61 g (0.005 mol) of Ib and 0.30 g
(0.0025 mol) of ethanedithioamide. Yield 1.53 g
(80%), mp 118–120°C. IR spectrum, ν, cm–1: 3228,
Compounds IVb and IVc were synthesized in
a similar way.
N-[2,2-Dichloro-1-(4-chlorophenylsulfonyl-
amino)-2-phenylethyl]ethanedithioamide (IVb) was
synthesized from 1.82 g (0.005 mol) of IIb. Yield
2.30 g (95%), mp 149–152°C. IR spectrum, ν, cm–1:
1
3130 (NH), 1657, 1338, 1166 (SO2). H NMR spec-
3
trum (DMSO-d6), δ, ppm: 6.31 d.d (2H, CH, J = 9.0,
1
3245 (NH), 1583, 1571, 1345, 1169 (SO2). H NMR
9.5 Hz), 7.44 and 7.71 (8H, C6H4, AA′BB′), 9.57 d (2H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 4 2012

ROZENTSVEIG et al.
484
3
3
SO2NH, J = 9.0 Hz), 10.08 d (2H, NHC=S, J =
9.5 Hz). 13C NMR spectrum (DMSO-d6), δC, ppm:
74.0 (CH), 98.9 (CCl3); 128.7. 129.2, 138.2, 138.5
(C6H4); 185.31 (C=S). Found, %: C 28.30; H 1.72;
Cl 37.10; N 7.21; S 16.76. C18H14Cl8N4O4S4. Calculat-
ed, %: C 28.37; H 1.85; Cl 37.21; N 7.35; S 16.83.
(C6H4); 184.7 (C=S). Found, %: C 42.47; H 2.74;
Cl 25.03; N 6.51; S 15.05. C30H24Cl6N4O4S4. Calculat-
ed, %: C 42.62; H 2.86; Cl 25.16; N 6.63; S 15.17.
REFERENCES
1. Levkovskaya, G.G., Drozdova, T.I., Rozentsveig, I.B.,
N,N′-Bis[2,2,2-trichloro-1-(4-methylphenylsul-
fonylamino)ethyl]ethanedithioamide (Vc) was syn-
thesized from 1.51 g (0.005 mol) of Ic and 0.30 g
(0.0025 mol) of ethanedithioamide. Yield 1.26 g
(70%), mp 146–148°C. IR spectrum, ν, cm–1: 3259,
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1
3085 (NH), 1655, 1333, 1165 (SO2). H NMR spec-
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3
(2H, CH, J = 9.4, 9.5 Hz), 7.16 and 7.58 (8H, C6H4,
3
AA′BB′), 9.43 d (2H, SO2NH, J = 9.5 Hz), 10.10 d
3
(2H, NHC=S, J = 9.4 Hz). 13C NMR spectrum
(DMSO-d6), δC, ppm: 21.1 (CH3), 74.1 (CH), 99.3
(CCl3); 126.7, 129.4, 136.9, 143.4 (C6H4); 185.1
(C=S). Found, %: C 33.23; H 2.73; Cl 29.35; N 7.67;
S 17.68. C20H20Cl6N4O4S4. Calculated, %: C 33.30;
H 2.79; Cl 29.49; N 7.77; S 17.78.
Compounds VIa and VIb were synthesized as
described above for IVa using 2 equiv of imine
IIa or IIb.
N,N′-Bis[2,2-dichloro-2-phenyl-1-(phenylsul-
fonylamino)ethyl]ethanedithioamide (VIa) was syn-
thesized from 1.64 g (0.005 mol) of IIa and 0.30 g
(0.0025 mol) of ethanedithioamide. Yield 1.51 g
(78%), mp 93–95°C. IR spectrum, ν, cm–1: 3320, 3095
1
(NH), 1595, 1335, 1170 (SO2). H NMR spectrum
3
(DMSO-d6), δ, ppm: 6.45 d.d (2H, CH, J = 9.4,
9.8 Hz); 7.46 m, 7.47 m, 7.68 m, and 7.78 m (20H,
3
C6H5), 9.15 d (2H, SO2NH, J = 9.4 Hz), 10.06 d (2H,
NHC=S, 3J = 9.8 Hz). 13C NMR spectrum (DMSO-d6),
δC, ppm: 72.5 (CH), 93.3 (CCl2); 125.4, 128.0, 132.4,
139.1 (SO2C6H5); 127.2, 128.4, 130.4, 139.5 (C6H5);
185.3 (C=S). Found, %: C 46.48; H 3.31; Cl 18.39;
N 7.35; S 16.71. C30H26Cl4N4O4S4. Calculated, %:
C 46.40; H 3.37; Cl 18.26; N 7.21; S 16.51.
14. Roy, P. and Srivastava, S.K., Cryst. Growth Des., 2006,
vol. 6, p. 1921.
N,N′-Bis[2,2-dichloro-1-(4-chlorophenylsulfonyl-
amino)-2-phenylethyl]ethanedithioamide (VIb) was
synthesized from 1.82 g (0.005 mol) of IIb and 0.30 g
(0.0025 mol) of ethanedithioamide. Yield 1.80 g
(85%), mp 160–162°C. IR spectrum, ν, cm–1: 3310,
15. Lapinski, L., Rostkowska, H., Khvorostov, A.,
Yaman, M., Fausto, R., and Nowak, M.J., J. Phys.
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1
3112 (NH), 1577, 1345, 1169 (SO2). H NMR spec-
3
trum (DMSO-d6), δ, ppm: 6.48 d.d (2H, CH, J = 9.3,
9.8 Hz), 7.44 and 7.62 (8H, C6H4, AA′BB′), 7.49 m and
7.66 m (10H, C6H5), 9.11 d (2H, SO2NH, 3J = 9.3 Hz),
10.08 d (2H, NHC=S, 3J = 9.8 Hz). 13C NMR spectrum
(DMSO-d6), δC, ppm: 72.6 (CH), 93.4 (CCl2); 127.4,
128.4, 130.0, 138.9 (C6H5); 128.5, 128.9, 136.9, 137.8
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 4 2012