Noncatalytic C-amidoalkylation of acetylacetone and chromium acetylacetonate with N-sulfonyl polychloroacetaldehyde imines

Article abstract of DOI:10.1134/S1070428014010011

N-(2,2,2-Trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene) arenesulfonamides reacted with acetylacetone and chromium(III) acetylacetonate in the absence of a catalyst to give previously unknown β-aminoketone derivatives, N-(3-acetyl-1-polychloro-4-oxopentan-2-yl)arenesulfonamides.

Full text of DOI:10.1134/S1070428014010011

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2014, Vol. 50, No. 1, pp. 1–5. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © I.B. Rozentsveig, G.N. Chernysheva, G.G. Levkovskaya, A.I. Fedotova, E.V. Tret’yakov, G.V. Romanenko, 2014, published in
Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 9–13.
Noncatalytic C-Amidoalkylation of Acetylacetone and Chromium
Acetylacetonate with N-Sulfonyl Polychloroacetaldehyde Imines
I. B. Rozentsveiga, G. N. Chernyshevaa, G. G. Levkovskayaa, A. I. Fedotovaa,
E. V. Tret’yakovb, and G. V. Romanenkob
a Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: i_roz@irioch.irk.ru
b International Tomography Center, Siberian Branch, Russian Academy of Sciences,
Institutskaya ul. 3A, Novosibirsk, 630090 Russia
Received July 31, 2013
Abstract—N-(2,2,2-Trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides reacted
with acetylacetone and chromium(III) acetylacetonate in the absence of a catalyst to give previously unknown
β-aminoketone derivatives, N-(3-acetyl-1-polychloro-4-oxopentan-2-yl)arenesulfonamides.
DOI: 10.1134/S1070428014010011
Halogen-substituted aldehyde and ketone imines
are important representatives of Schiff bases. The pres-
ence in their molecules of two highly electrophilic
centers, electron-deficient carbon atom of the azo-
methine fragment and halomethyl carbon atom, makes
such imines very reactive toward nucleophiles, as well
as toward aromatic and heteroaromatic compounds,
which opens efficient synthetic routes to various func-
tionalized acyclic and heterocyclic derivatives [1–11].
N-Sulfonyl imines I and II are highly electrophilic
activated halogenated aldimines which have become
accessible due to development of methods for their
preparation by radical reactions of N,N-dichloroarene-
sulfonamides with trichloroethylene and phenylacety-
lene [1, 19–21] (Scheme 1). The best yields of adducts
IIIa, IIIb, IVa, and IVb were achieved by heating the
reactants in dimethylformamide for 10 h at 100°C. The
reaction required no any catalytic system, though such
systems are commonly used [12–17] to accomplish
analogous transformations in the series of Schiff bases
derived from aromatic, aliphatic, or functionalized
aldehydes. The yields of IIIa, IIIb, IVa, and IVb in
other solvents or under solvent-free conditions, as well
Research works on the reactivity of imines derived
from polyhalocarbonyl compounds remain topical. It is
known [12–17] that reactions of Schiff bases with
1,3-dicarbonyl compounds acting as carbon-centered
nucleophiles provide highly efficient methods for the
preparation of practically useful aminocarbonyl com-
pounds which exhibit biological activity and attract
interest as subjects for stereochemical and theoretical
studies [18]. However, such reactions of 1,3-dicar-
bonyl compounds with N-sulfonyl imines of polyhalo-
carbonyl compounds have not been reported.
Scheme 1.
ClCH=CCl2
Cl
ArSO2NCl2
+ or
N
Cl
ArSO2
X
HC
Ph
Ia, Ib, IIa, IIb
Cl
H
N
In the present work we examined reactions of
N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-
phenylethylidene)arenesulfonamides I and II with
acetylacetone and chromium(III) acetylacetonate with
a view to develop synthetic approaches to new
N-substituted halogen derivatives of aminocarbonyl
compounds.
Cl
X
Ia, Ib, IIa, IIb
DMF, 10 h, 100°C
ArSO2
Me
Me
Me
Me
O
O
O
O
IIIa, IIIb, IVa, IVb
I, III, X = Cl; II, IV, X = Ph; Ar = 4-ClC6H4 (a), 4-MeC6H4 (b).
1

ROZENTSVEIG et al.
2
Scheme 2.
4-ClC6H4SO2NH
CCl3
Me
Me
Me
Me
O
O
O
O
O
O
Ia, CCl4
4–6 h, 60°C
Concd. aq. HCl
30 h, 90°C
CCl3
O
Me
O
Me
O
O
Me
O
Me
Cr
Cr
4-ClC6H4SO2NH
Me
O
O
Me
Me
Me
Me
V
VI
as in the reactions carried out at room temperature,
were considerably lower.
mixed-ligand complex V (Scheme 2). Unlike acetyl-
acetone, the reaction of Ia with chromium(III) acetyl-
acetonate occurred under milder conditions (CCl4,
60°C) and was complete in 4–6 h.
The structure of sulfonamides IIIa, IIIb, IVa, and
1
13
IVb was unambiguously proved by H and C NMR
1
The structure of complex V was unambiguously
determined by X-ray analysis (see figure and table).
Crystals of compound V are made up of centrosym-
metric dimers formed via intermolecular hydrogen
bonds N–H · · · O=S with an N · · · O distance of
2.961(3) Å. Insofar as the coordination environment of
the chromium atom includes different acetylacetonate
ligands, the octahedral coordination entity is slightly
distorted, and the Cr–O distances range from 1.932(2)
to 1.963(2) Å.
and IR spectra and elemental analyses. Their H NMR
spectra contained signals from aromatic protons and
those typical of the NHCHCH fragment, namely
a doublet of doublets at δ 5.02–5.34 ppm from the
NCH proton, a doublet at δ 4.36–4.37 ppm (3J = 2.4–
2.7 Hz) from the CH group located between the car-
bonyl groups, and a downfield doublet at δ 6.9–8.2 ppm
(3J = 9.1–9.2 Hz) from the NH proton. The methyl and
carbonyl groups in the acetylacetone fragment are
magnetically nonequivalent, and two sets of the corre-
1
13
sponding signals are observed in the H and C NMR
spectra in CDCl3 and DMSO-d6. The presence in the
1H NMR spectra of a doublet signal from the CH
proton with a coupling constant corresponding to spin–
spin interaction through three bonds indicates that
compounds IIIa, IIIb, IVa, and IVb in organic
solvents have diketone structure.
Compound V displayed in the IR spectrum absorp-
tion bands belonging to stretching vibrations of the NH
and SO2 groups, as well as carbonyl stretching vibra-
tion bands whose frequencies differed from those
characteristic of the initial acetylacetonate. Signals in
the NMR spectra of V were appreciably broadened due
to the presence of paramagnetic chromium atom.
Like acetylacetone, metal acetylacetonates can also
be involved in reactions with activated halogenated
acetaldehyde imines. As an example, Schiff base Ia
reacted with chromium(III) acetylacetonate to give
The structure of V was also confirmed by chemical
transformations. The hydrolysis with aqueous HCl
induced decomposition of the complex and cleavage of
the β-dicarbonyl fragment with quantitative formation
C11
C12
Cl25
C10
O14
Cl24
O8
Cr
C23
C19
Cl26
N27
O21
O7
C18
C22
O1
C3
C5
O15
C17
C4
S28 O30
C31
O29
Structure of complex V (dimer) according to the X-ray diffraction data.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 1 2014

NONCATALYTIC C-AMIDOALKYLATION OF ACETYLACETONE
3
Some interatomic distances and bond angles in the crystalline structure of compound V (dimer) according to the X-ray
diffraction data
Distance
d, Å
Angle
ω, deg
Angle
ω, deg
Cr–O15
Cr–O14
Cr–O21
Cr–O7
1.9297(19)
1.947(2)
1.9526(19)
1.9548(19)
1.959(2)
1.962(2)
1.269(4)
1.390(4)
1.383(5)
1.280(4)
1.263(4)
1.392(5)
1.387(5)
1.273(4)
1.271(3)
1.418(4)
1.428(4)
1.523(4)
1.274(3)
1.467(3)
1.551(5)
1.732(4)
1.752(4)
1.763(3)
1.616(3)
1.420(2)
1.430(2)
1.761(3)
O15CrO14
O15CrO21
O14CrO21
O15CrO7
O14CrO7
O21CrO7
O15CrO1
O14CrO1
O21CrO1
O7CrO1
088.59(9)
086.16(8)
088.00(9)
178.81(9)
090.74(9)
092.84(8)
090.00(9)
178.30(9)
090.95(9)
090.65(9)
089.96(8)
090.12(9)
175.73(9)
091.02(8)
090.84(9)
127.5(2)
124.8(3)
124.8(3)
125.1(3)
127.1(2)
126.0(2)
124.3(3)
125.1(3)
124.0(3)
126.2(2)
130.34(17)
123.7(2)
119.8(3)
C17C18C22
C19C18C22
O21C19C18
C18C19C20
C19O21Cr
N27C22C18
N27C22C23
C18C22C23
C22C23Cl24
C22C23Cl26
Cl24C23Cl26
C22C23Cl25
Cl24C23Cl25
Cl26C23Cl25
C22N27S28
O30S28O29
O30S28N27
O29S28N27
O30S28C31
O29S28C31
N27S28C31
123.3(2)
116.4(2)
124.4(3)
122.7(3)
Cr–O1
128.94(18)
117.8(2)
Cr–O8
O1–C3
108.5(2)
C3–C4
116.3(3)
C4–C5
114.5(2)
C5–O7
111.7(3)
O8–C10
C10–C11
C11–C12
C12–O14
O15–C17
C17–C18
C18–C19
C18–C22
C19–O21
C22–N27
C22–C23
C23–Cl24
C23–Cl26
C23–Cl25
N27–S28
S28–O30
S28–O29
S28–C31
O15CrO8
O14CrO8
O21CrO8
O7CrO8
099.6(2)
109.7(2)
112.6(2)
108.22(19)
121.15(19)
120.17(13)
107.14(13)
106.24(13)
107.88(15)
107.54(14)
107.25(14)
O1CrO8
C3O1Cr
O1C3C4
C5C4C3
O7C5C4
C5O7Cr
C10O8Cr
O8C10C11
C12C11C10
O14C12C11
C12O14Cr
C17O15Cr
O15C17C18
C17C18C19
of a previously unknown β-amino ketone, 4-chloro-N-
their precursors and important reagents whose syn-
thetic value is increased due to the presence of a poly-
chloromethyl fragment. We also found that coordina-
tion of acetylacetone to transition metals facilitates its
reaction with chlorinated N-sulfonyl imines. Taking
into account that diketone functionalized in such a way
can be isolated as individual compound, this technique
may be regarded as a methodical approach to activa-
tion of β-dicarbonyl compounds toward aldehyde and
ketone imines.
[3-oxo-1-(trichloromethyl)butyl]benzenesulfonamide
1
(VI) (Scheme 2). The H NMR spectrum of VI con-
tained signals from protons in the para-substituted
benzene ring, a singlet from the methyl group, and
multiplet signals typical of the NHCHCH2 fragment.
These findings in combination with the IR data
(absorption bands due to SO2 and NH groups) and
elemental analysis provide reliable proof of the
assumed structure.
To conclude, we were the first to reveal that
N-sulfonyl imines derived from trichloroacetaldehyde
and dichloro(phenyl)acetaldehyde are capable of react-
ing with acetylacetone to produce previously unknown
β-amino ketone derivatives. The products attract
interest as potentially biologically active substances or
EXPERIMENTAL
The H and 13C NMR spectra were recorded on
a Bruker DPX-400 spectrometer at 400.61 and
100.13 MHz, respectively, using tetramethylsilane as
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 1 2014

ROZENTSVEIG et al.
4
internal reference. The IR spectra were taken in KBr
on a Bruker IFS-25 instrument. Imines Ia, Ib, IIa, and
IIb were synthesized according to the procedures
described in [19–21].
13C NMR spectrum (CDCl3), δC, ppm: 29.33 (CH3),
32.53 (CH3), 64.27 [C(O)CHC(O)], 67.45 (NCH),
95.36 (CCl2); 127.45, 128.31, 128.51, 129.00, 138.65,
138.83, 139.39, 144.12 (Carom); 200.03 (C=O), 205.12
(C=O). Found, %: C 49.22; H 3.97; Cl 22.85; N 3.15;
S 7.01. C19H18Cl3NO4S. Calculated, %: C 49.31;
H 3.92; Cl 22.98; N 3.03; S 6.93.
N-(3-Acetyl-1,1,1-trichloro-4-oxopentan-2-yl)-
4-chlorobenzenesulfonamide (IIIa). A mixture of
3.21 g (0.01 mol) of imine Ia, 1.00 g (0.01 mol) of
acetylacetone, and 5 mL of DMF was stirred for 10 h
at 100°C. The mixture was cooled to room temperature
and diluted with 50 mL of water, and the precipitate
was filtered off, dried, and purified by reprecipitation
from acetone into water. Yield 3.45 g (82%), mp 115–
117°C. IR spectrum, ν, cm–1: 3280 (NH); 1705 (C=O);
1343, 1164 (SO2). 1H NMR spectrum (CDCl3), δ, ppm:
2.28 s (3H, CH3), 2.30 s (3H, CH3), 4.50 d [1H,
N-(3-Acetyl-1,1-dichloro-4-oxo-1-phenylpentan-
2-yl)-4-methylbenzenesulfonamide (IVb) was syn-
thesized from 3.42 g (0.01 mol) of imine IIb. Yield
3.71 g (84%), mp 103–105°C. IR spectrum, ν, cm–1:
1
3232 (NH); 1702 (C=O); 1333, 1156 (SO2). H NMR
spectrum (DMSO-d6), δ, ppm: 1.81 s (3H, CH3),
2.16 (3H, CH3), 2.33 s (3H, CH3), 4.37 d [1H,
3
3
C(O)CHC(O), J = 7.1 Hz], 5.34 d.d (1H, NCH, J =
3
3
C(O)CHC(O), J = 3.0 Hz], 5.02 d.d (1H, NCH, J =
7.1, 10.0 Hz); 7.20 m, 7.28 m, 7.48 m, and 7.56 m (9H,
3
H
arom); 8.22 d (1H, NH, 3J = 10.0 Hz). 13C NMR spec-
3.0, 9.1 Hz), 7.17 d (1H, NH, J = 9.1 Hz), 7.43 and
7.79 (4H, AA′BB′, C6H4). 13C NMR spectrum (CDCl3),
δC, ppm: 29.47 and 32.95 (CH3), 63.46 [C(O)CHS(O)],
68.71 (NCH), 101.42 (CCl3); 128.60, 128.72, 129.95,
139.40 (C6H4); 199.00 (C=O), 205.10 (C=O). Found,
%: C 37.02; H 3.06; Cl 33.48; N 3.25; S 7.50.
C13H13Cl4NO4S. Calculated, %: C 37.08; H 3.11;
Cl 33.67; N 3.33; S 7.61.
trum (DMSO-d6), δC, ppm: 20.74 (CH3), 29.06 (CH3),
31.02 (CH3), 64.05 [C(O)CHC(O)], 67.34 (NCH),
96.13 (CCl2); 125.86, 127.32, 128.02, 128.71, 129.49,
138.23, 139.12, 141.78 (Carom); 199.19 (C=O), 200.72
(C=O). Found, %: C 54.22; H 4.67; Cl 15.95; N 3.05;
S 7.18. C20H21Cl2NO4S. Calculated, %: C 54.30;
H 4.79; Cl 16.03; N 3.17; S 7.25.
Compounds IIIb, IVa, and IVb were synthesized in
a similar way.
{3-[1-(4-Chlorobenzenesulfonamido)-2,2,2-tri-
chloroethyl]pentane-2,4-dionato}bis(acetylaceto-
nato)chromium(III) (V). A mixture of 3.21 g
(0.01 mol) of imine Ia and 3.49 g (0.01 mol) of
chromium(III) acetylacetonate in 25 mL of carbon
tetrachloride was stirred for 6 h at 60°C in a stream of
argon. The precipitate was filtered off and recrystal-
lized from carbon tetrachloride–acetone (4:1). Yield
5.18 g (77%), mp 143–145°C. IR spectrum, ν, cm–1:
3227 (NH); 1588 (C=O); 1526 (C=C); 1348, 1149
(SO2). Found, %: C 41.36; H 4.23; Cl 21.22; N 2.21;
S 4.54. C23H32Cl4CrNO8S. Calculated, %: C 41.03;
H 4.34; Cl 21.06; N 2.08; S 4.76.
N-(3-Acetyl-1,1,1-trichloro-4-oxopentan-2-yl)-
4-methylbenzenesulfonamide (IIIb) was synthesized
from 3.01 g (0.01 mol) of imine Ib. Yield 3.12 g
(78%), mp 97–99°C. IR spectrum, ν, cm–1: 3342 (NH);
1
1730 (C=O); 1328, 1163 (SO2). H NMR spectrum
(CDCl3), δ, ppm: 2.23 s (3H, CH3), 2.24 s (3H, CH3),
3
2.38 s (3H, CH3), 4.47 d [1H, C(O)CHC(O), J =
3
2.6 Hz], 5.02 d.d (1H, NCH, J = 2.6, 9.1 Hz), 7.05 d
3
(1H, NH, J = 9.1 Hz), 7.24 and 7.70 (4H, AA′BB′,
C6H4). 13C NMR spectrum (CDCl3), δC, ppm:
21.56 (CH3), 29.44 (CH3), 32.76 (CH3), 63.66
[C(O)CHC(O)], 68.61 (NCH), 101.62 (CCl3); 127.13,
129.45, 137.98, 143.76 (C6H4); 199.33 (C=O), 205.07
(C=O). Found, %: C 41.84; H 3.96; Cl 26.47; N 3.41;
S 7.87. C14H16Cl3NO4S. Calculated, %: C 41.96;
H 4.02; Cl 26.54; N 3.50; S 8.00.
4-Chloro-N-(1,1,1-trichloro-4-oxopentan-2-yl)-
benzenesulfonamide (VI). A mixture of 6.73 g
(0.01 mol) of compound V and 25 mL of concentrated
aqueous HCl was stirred for 30 h at 90°C. The precip-
itate was filtered off, washed with water, and dried
under reduced pressure. Yield 3.71 g (98%), mp 204–
206°C. IR spectrum, ν, cm–1: 3243 (NH); 1583 (C=O);
N-(3-Acetyl-1,1-dichloro-4-oxo-1-phenylpentan-
2-yl)-4-chlorobenzenesulfonamide (IVa) was synthe-
sized from 3.63 g (0.01 mol) of imine IIa. Yield 3.70 g
(80%), mp 140–142°C. IR spectrum, ν, cm–1: 3218
1
1350, 1164 (SO2). H NMR spectrum (DMSO-d6), δ,
ppm: 1.87 s (3H, CH3), 2.72 and 3.12 (2H, CH2, ABX,
2
3
3J = 6.6, 3.0, J = 18.1 Hz), 4.57 m (1H, CH, J =
1
(NH); 1703 (C=O); 1339, 1168 (SO2). H NMR spec-
6.6, 3.0, 8.9 Hz), 7.64 and 7.76 (4H, AA′BB′, C6H4),
trum (CDCl3), δ, ppm: 2.19 s (3H, CH3), 2.27 s (3H,
3
8.85 d (1H, NH, J = 8.9 Hz). 13C NMR spectrum
CH3), 4.36 d [1H, C(O)CHC(O), 3J = 2.4 Hz], 5.17 d.d
3
3
(1H, NCH, J = 2.4, 9.2 Hz), 6.87 d (1H, NH, J =
(DMSO-d6), δC, ppm: 29.50 (CH3), 45.14 (CH2), 63.49
9.2 Hz); 7.33 m, 7.57 m, and 7.67 m (9H, Harom).
(NCH), 102.68 (CCl3); 128.22, 129.02, 137.26, 140.30
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 1 2014

NONCATALYTIC C-AMIDOALKYLATION OF ACETYLACETONE
5
3. De Kimpe, N., Verhé, R., De Buyck, L., and
Schamp, N., Org. Prep. Proced. Int., 1980, vol. 12,
p. 49.
(C6H4); 202.94 (C=O). Found, %: C 34.78; H 2.99;
Cl 37.63; N 3.84; S 8.75. C11H11Cl4NO3S. Calculated,
%: C 34.85; H 2.92; Cl 37.41; N 3.69; S 8.46.
4. Mangelinckx, S., Giubellina, N., and De Kimpe, N.,
X-Ray diffraction study of compound V. Reflec-
tion intensities from a single crystal of complex V
were measured on a Bruker Smart Apex CCD dif-
fractometer at 240 K (MoKα radiation, λ 0.71073 Å).
Absorption by the crystal was taken into account using
SADABS program. The structure was solved by the
direct method and was refined by the full-matrix least-
squares method in anisotropic approximation for all
non-hydrogen atoms. The positions of hydrogen atoms
were calculated geometrically and were refined
according to the riding model. Difference syntheses of
electron density revealed peaks corresponding to
a solvent molecule, but we failed to localize it reliably;
therefore, it was excluded from the refinement in the
final step (SQUEEZE function in PLATON program
[22]). All calculations were performed using Bruker
SHELXTL Version 6.14. Crystallographic parameters
of compound V: triclinic crystal system, space group
P-1; a = 7.6101(4), b = 11.6074(7), c = 18.7245(11) Å;
α = 101.136(3), β = 101.675(3), γ = 97.682(3)°; V =
1563.4(2) Å3; Z = 2; dcalc = 1.424 g/cm3; μ =
0.816 mm–1; 1.14 < θ < 28.29°. Total of 25921 reflec-
tion intensities were measured, 7650 of which were
independent (Rint = 0.0674) and 7909 reflections were
characterized by I > 2σ(I); 361 refined parameters;
goodness of fit 0.827; final divergence factors R1 =
0.0497, wR2 = 0.1135 for reflections with I > 2σ(I),
R1 = 0.1155, wR2 = 0.1266 for all reflections (Ihkl);
maximum and minimum residual electron density
0.818/–0.483 e Å–3.
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This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 12-03-31 762), by the Siberian Branch of the
Russian Academy of Sciences (project no. 21), and by
the Belarusian Republican Foundation for Fundamen-
tal Research (project no. Kh12SO-012). The main
results were obtained using the facilities of the Baikal
Joint Analytical Center, Siberian Branch, Russian
Academy of Sciences.
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p. 5797.
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