Green and Sustainable Chemistry, 2011, 1, 31-35
doi:10.4236/gsc.2011.12006 Published Online May 2011 (http://www.SciRP.org/journal/gsc)
Synthesis of Novel Bis-Enaminones by KHSO4-Assisted
Facile Michael Addition-Elimination Reaction of
3-(Dimethylamino)-1-phenylprop-2-en-1-ones with
Diamines in Water#
Asem Satyapati Devi1, Philippe Helissey2, Jai Narain Vishwakarma1*
1Organic Research Lab., Department of Chemistry, St. Anthony’s College, Shillong, India
2Laboratoire de Chimie Thérapeutique, Faculte des Sciences Pharmaceutiques et Biologiques,
Université Paris Descartes, Paris, France
Received March 30, 2011; revised April 30, 2011; accepted May 12, 2011
Abstract
3-(Dimethylamino)-1-phenylprop-2-en-1-ones (formylated acetophenones) 1 reacted with aliphatic diamines
in water assisted by KHSO4 to give bis-enaminones 2a-h in good yields. Compound 1 also reacted with
o-phenylenediamine under similar conditions to produce bis-enaminones 3 instead of benzodiazepines 4 in
excellent yields.
Keywords: Enaminone, Bis-Enaminone, Formylated Acetophenone, Michael Addition-Elimination,
Formylation, Dimethylformamide-Dimethylacetal
1. Introduction
Formylated products obtained by reacting active proton
compounds with dimethylformamide-dimethylacetal
(DMF-DMA) have proved to be very useful intermedi-
ates in the formation and modification of heterocyclic
compounds [1]. Keeping in view the synthetic potential
of 3-(dimethylamino)-1-phenylprop-2-en-1-ones (for-
mylated acetophenones) [2-12], we recently reported an
efficient method for the formylation of active proton
compounds [13]. We subsequently developed a facile
synthetic strategy for the synthesis of enaminones by
reacting formylated acetophenones with primary amines
[14]. These enaminones were then transformed into tet-
rahydropyrimidines [15] and bis-tetrahydropyrimidines
[16].
In view of the environmental concerns, carrying out
organic reactions in water has attracted considerable at-
tention [17-29]. We have, from our laboratory, recently
reported [30] a facile general reaction of formylated ace-
tophenones with primary amines in water.
In connection with our synthetic studies on enami-
nones, we required bis-enaminones derived from aceto-
phenones. Our literature survey at this stage revealed that
bis-enaminones derived from acetophenones have re-
ceived very little attention [31] and hence examination of
their biological properties and synthetic potential has
remained unexplored. Prompted by the above facts, we
herein report a facile general strategy for the reaction of
formylated acetophenones with primary diamines as-
sisted by KHSO4 in water that lead to the formation of
novel bis-enaminones in excellent yields.
2. Results and Discussion
Thus, when formylated acetophenone 1a was reacted
with ethylenediamine in water in the presence of KHSO4,
bis-enaminone 2a was obtained in 88% yields. The
structure of 2a was established as 1,2-bis-[3-oxo-3-
phenylpropenylamino]ethane on the basis of spectral and
analytical data. Thus, the IR spectra of 2a showed peaks
at 1581, 1638, 3249, 3388 cm–1 due carbonyl and NH
groups. In the NMR spectra of 2a, the NCH2 protons
resonated as multiplets at 3.44 - 3.46 ppm. The α-vinylic
proton appeared as a doublet at 5.73 ppm (J = 7.2 Hz),
while the β-vinylic proton gave a double-doublet at 6.88
ppm (J = 7.2, 12.4 Hz) due to its coupling with α-vinylic
as well as NH protons. On D2O shake, the signal at 5.73
#This paper is dedicated to Rev Fr Dr. I Warpakma, SDB on his 50th
birth anniversary.

32 A. S. DEVI ET AL.
ppm remained unchanged whereas the signal at 6.88 was
reduced to a doublet (J = 7.2 Hz). The aromatic protons
appeared in their usual range. The NH proton resonated
at 10.35 ppm indicating its hydrogen bonded state. The
low coupling constant of the vinylic protons and the ap-
pearance of the NH signal at low fields confirm the
Z-configuration of the enaminones.
The reaction of 1a with 1,4-diaminobutane gave the
expected products 2b in 84% yield under identical condi-
tions. Other formylated acetophenones 1b-e behaved
identically with aliphatic diamines forming the envisaged
products in good yields (Scheme 1). The structures of
bis-enaminones 2b-h were also established with the help
of spectral and analytical data and in all cases the
enaminone moieties were found to exist exclusively in
Z-form.
Subsequently, we planned to examine the reactions of
o-phenylenediamine with 1a envisaging the formation of
benzodiazepines of the type 4 (Scheme 2). However,
when the reaction was carried out, the product isolated in
94% yield was found to be bis-enaminone 3a, the struc-
ture of which was well established with the help of spec-
tral and analytical data. Thus, the 1H NMR spectra of 3a
showed a doublet at 6.14 ppm (J = 7.8 Hz) for the vinylic
proton at C-α whereas the vinylic proton at C-β, which is
expected to appear as double-doublet was obscured by
the aromatic proton signals between 7.39 - 7.52 ppm.
Other aromatic protons resonated in their usual range.
The N-H protons in this case appeared as doublet at
12.21 ppm indicating that these are hydrogen bonded
with the carbonyl group. This appearance of N-H proton
at 12.21 ppm and the low coupling constant of vinylic
proton at C-α confirm Z-configuration of the enaminone
moieties. 1b-e also behaved identically with o-phenylene
diamine under similar conditions giving bis-enaminones
3b-e. In none of these cases, product 4 was formed even
with varying stoichiometry of 1 and o-phenylene diamine.
Scheme 2
3. Experimental Section
Melting points were recorded by open capillary method
and are uncorrected. The IR spectra were recorded on a
Perkin-Elmer 983 spectrometer. 1H NMR and 13C NMR
spectra were recorded on Bruker ACF-300 spectrometer.
The chemical shifts (δ ppm) and the coupling constants
(Hz) are reported in the standard fashion with reference
to TMS as internal reference. FAB-mass spectra (MS)
were measured on JEOL 3SX 102/DA-6000 mass spec-
trometer using argon as the carrier and m-nitro-benzy-
lalcohol as the matrix. Elemental analyses were per-
formed on a Vario-EL III instrument. Formylated aceto-
phenones 1a-e were synthesized by our previously re-
ported procedure [13].
3.1. Reaction of 3-Dimethylamino-1-Arylpro-
penone 1 with Aliphatic Diamines
General Procedure. To a mixture of 1 (2 mmol) and
aliphatic diamine (1 mmol) in 5 ml water was added
KHSO4 (2 mmol) in one lot and the resulting mixture
was stirred at 50˚C - 60˚C for 1-2 hours. After the com-
pletion of the reaction (tlc), the reaction mixture was
cooled and the precipitated product was collected by
filtration. The product 2 thus obtained was found to be
practically pure, which however was chromatographed
(silica gel, ethyl acetate).
1,2-Bis-[3-oxo-3-phenylpropenylamino]ethane (2a).
Pale yellow solid in 88% yield, mp 140˚C - 141˚C (lit.
[31] 142˚C); IR (KBr): 1581, 1638, 3249, 3388 cm–1;

A. S. DEVI ET AL.
33
1HNMR (CDCl3): δ 3.44 - 3.46 (m, 4H), 5.73 (d, 2H, J =
7.2 Hz), 6.88 (dd, 2H, J = 7.2, 12.4 Hz), 7.39 - 7.46 (m,
6H), 7.85 - 7.87 (m, 4H), 10.35 (br m, 2H); 13CNMR
(CDCl3): δ 50.2, 91.2, 127.1, 128.3, 131.1, 139.4, 154.4,
190.5. MS: m/z 321 (MH+).
1,4-Bis-[3-oxo-3-phenylpropenylamino]butane (2b).
Pale yellow solid in 84% yield, mp 121˚C - 122˚C; IR
(KBr): 1582, 1633, 3268 cm–1; 1HNMR (CDCl3): δ 1.53 -
1.71 (m, 4H), 3.31 - 3.33 (m, 4H), 5.71 (d, 2H, J = 7.6
Hz), 6.94 (dd, 2H, J = 7.6, 12.8 Hz), 7.39 - 7.45 (m, 6H),
7.86 - 7.87 (m, 4H), 10.38 (br m, 2H); 13CNMR (CDCl3):
δ 28.2, 48.8, 90.3, 127.0, 128.2, 130.9, 139.6, 154.2,
190.0. MS: m/z 349 (MH+).
Anal. Calcd for C22H24N2O2: C, 75.83; H, 6.94; N,
8.04. Found: C, 76.01; H, 6.88; N, 8.09%.
1,2-Bis-[3-oxo-3-(4-methylphenyl)propenylamino]et
hane (2c). Pale yellow solid in 85% yield, mp 192˚C -
193˚C; IR (KBr): 1579, 1641, 3278 cm–1; 1HNMR
(CDCl3): δ 2.39 (s, 6H), 3.43 - 3.49 (m, 4H), 5.71 (d, 2H,
J = 7.6 Hz), 6.85 (dd, 2H, J = 7.6, 12.4 Hz), 7.21 (d, 4H,
J = 8 Hz), 7.76 (d, 4H, J = 8 Hz), 10.31 (br m, 2H).
13CNMR (CDCl3): δ 21.4, 50.2, 91.1, 127.2, 128.9, 136.8,
141.5, 154.1, 190.3. MS: m/z 349 (MH+).
Anal. Calcd for C22H24N2O2: C, 75.83; H, 6.94; N,
8.04. Found: C, 75.70; H, 6.89; N, 8.10%.
1,4-Bis-[3-oxo-3-(4-methylphenyl)propenylamino]b
utane (2d). Pale yellow solid in 91% yield, mp 163˚C -
164˚C; IR (KBr): 1579, 1608, 1636, 3285, 3435 cm–1;
1HNMR (CDCl3): δ 1.63 - 1.70 (m, 4H), 2.38 (s, 6H),
3.30 - 3.31 (m, 4H), 5.69 (d, 2H, J = 7.2 Hz), 6.91 (dd,
2H, J = 7.2, 12.8 Hz), 7.21 (d, 4H, J = 8 Hz), 7.77 (d, 4H,
J = 8 Hz), 10.33 (br, s, 2H); 13CNMR (CDCl3): δ 21.4,
28.2, 48.8, 90.2, 127.1, 128.9, 137.0, 141.3, 153.9, 189.9;
MS: m/z 377 (MH+), 378 (MH+ + 1).
Anal. Calcd for C24H28N2O2: C, 76.56; H, 7.50; N,
7.44. Found: C, 76.72; H, 7.43; N, 7.61%.
1,2-Bis-[3-oxo-3-(4-chlorophenyl)propenylamino]et
hane (2e). Pale yellow solid in 89% yield, mp 200˚C -
201˚C; IR (KBr): 1578, 1629, 3257, 3395 cm–1; 1HNMR
(CDCl3): δ 3.45 - 3.47 (m, 4H), 5.68 (d, 2H, J = 7.6 Hz),
6.89 (dd, 2H, J = 7.6, 12.4 Hz), 7.38 (d, 4H, J = 8.4 Hz),
7.79 (d, 4H, J = 8.4 Hz), 10.35 (br, s, 2H); 13CNMR
(CDCl3): δ 49.9, 90.6, 128.3, 128.4, 132.1, 137.3, 154.7,
186.5. MS: m/z 389 (MH+).
Anal. Calcd for C20H18Cl2N2O2: C, 61.71; H, 4.66; N,
7.20. Found: C, 61.52; H, 4.61; N, 7.11%.
1,4-Bis-[3-oxo-3-(4-chlorophenyl)propenylamino]b
utane (2f). Pale yellow solid in 93% yield, mp 176˚C
-177˚C; IR (KBr): 1578, 1634, 3289, 3428 cm–1; 1HNMR
(CDCl3): δ 1.71 (br, s, 4H), 3.32 - 3.33 (m, 4H), 5.66 (d,
2H, J = 7.2 Hz), 6.95 (dd, 2H, J = 7.6, 12.8 Hz), 7.37 (d,
4H, J = 8.4 Hz), 7.79 (d, 4H, J = 8.4 Hz), 10.37 - 10.40
(br, m, 2H); 13CNMR (CDCl3): δ 28.1, 48.9, 90.7, 128.4,
128.4, 137.0, 138.0, 154.5, 188.5; MS: m/z 419 (MH+),
417 (MH+).
Anal. Calcd for C22H22 Cl2N2O2: C, 63.32; H, 5.31; N,
6.71. Found: C, 63.11; H, 5.37; N, 6.65%.
1,2-Bis-[3-oxo-3-(4-methoxyphenyl)propenylamino]
ethane (2g). Pale yellow solid in 88% yield, mp 184˚C
-185˚C; IR (KBr): 1582, 1601, 1645, 3293, 3433 cm–1;
1HNMR (CDCl3): δ 3.41 - 3.43 (m, 4H), 3.85 (s, 6H),
5.68 (d, 2H, J =7.6 Hz), 6.84 (dd, 2H, J = 7.6, 12.4 Hz),
6.90 (d, 4H, J = 8.4 Hz), 7.85 (d, 4H, J = 8.4 Hz), 10.21
(br, s, 2H); MS: m/z 381 (MH+).
Anal. Calcd for C22H24N2O4: C, 69.46; H, 6.36; N,
7.36. Found: C, 69.31; H, 6.43; N, 7.28%.
1,4-Bis-[3-oxo-3-(4-methoxyphenyl)propenylamino]
butane (2h). Pale yellow solid in 94% yield, mp 161˚C -
162˚C; IR (KBr): 1582, 1600, 1636, 3292, 3433 cm–1;
1HNMR (CDCl3): δ 1.69 (br, s, 4H), 3.29 - 3.30 (br, m,
4H), 3.85 (s, 6H), 5.66 (d, 2H, J = 7.2 Hz), 6.87 - 6.92
(m, 6H), 7.85 (d, 4H, J = 8.8 Hz), 10.26 - 10.29 (br m,
2H); 13CNMR (CDCl3): δ 28.2, 48.8, 55.3, 89.8, 113.4,
128.9, 132.4, 153.7, 161.9, 189.2; MS: m/z 409 (MH+).
Anal. Calcd for C24H28N2O4: C, 70.57; H, 6.91; N,
6.86. Found: C, 70.80; H, 6.95; N, 6.81%.
3.2. Reaction of 3-Dimethylamino-1-Arylpro-
penone 1 with 1,2-Diaminobenzene
General Procedure. To a mixture of 1 (2 mmol) and
aromatic diamine (1 mmol) in 5 ml water was added
KHSO4 (2 mmol) in one lot and the resulting mixture
was stirred at 50˚C - 60˚C for 1.5 - 4 hours. After the
completion of the reaction (tlc), the reaction mixture was
cooled and the precipitated product was collected by
filtration. The product 3 thus obtained was found to be
practically pure, which however was chromatographed
(silica gel, ethyl acetate).
1,2-Bis-[3-oxo-3-phenylpropenylamino]benzene
(3a). Yellow solid, 94% yield, mp 300˚C; IR (KBr):
1597, 1625, 1639, 3422 cm–1; 1HNMR (CDCl3): δ 6.14
(d, 2H, J = 7.8 Hz), 7.14 -7.22 (m, 4H), 7.39 - 7.52 (m,
8H), 7.95 - 7.98 (m, 4H), 12.20 (d, 2H, J = 11.4 Hz);
13CNMR (CDCl3): δ 95.5, 119.0, 125.1, 127.5, 128.3,
131.5, 132.1, 139.1, 146.3, 191.2; MS: m/z 369 (MH+).
Anal. Calcd for C24H20N2O2: C, 78.24; H, 5.47; N,
7.60. Found: C, 78.02; H, 5.42; N, 7.66%.
1,2-Bis-[3-oxo-3-(4-methylphenyl)propenylamino]b
enzene (3b). Yellow solid, 88% yield, mp ›300˚C; IR
(KBr): 1609, 1634, 3432 cm–1; 1HNMR (CDCl3): δ 2.40
(s, 6H), 6.12 (d, 2H, J = 7.8 Hz), 7.12 - 7.25 (m, 8H),
7.39 (dd, 2H, J = 7.8, 11.4 Hz), 7.87 (d, 4H, J = 8.1 Hz),
12.16 (d, 2H, J = 11.4 Hz); 13CNMR (CDCl3): δ 21.5,
95.4, 118.8, 125.0, 127.6, 129.0, 132.1, 136.5, 142.0,
146.0, 191.0; MS: m/z 397 (MH+).

34 A. S. DEVI ET AL.
Anal. Calcd for C26H24N2O2: C, 78.76; H, 6.10; N,
7.07. Found: C, 78.97; H, 6.05; N, 7.12%.
1,2-Bis-[3-oxo-3-(4-chlorophenyl)propenylamino]be
nzene (3c). Yellow solid, 93% yield, mp ›300˚C; IR
(KBr): 1627, 3421 cm–1; 1HNMR (CDCl3): δ 6.06 (d, 2H,
J = 8.1 Hz), 7.12 - 7.19 (m, 4H), 7.36 -7.43 (m, 6H), 7.85
- 7.88 (m, 4H), 12.17 (d, 2H, J = 11.4 Hz); 13CNMR
(CDCl3): δ 95.1, 118.9, 125.4, 128.6, 128.9, 131.9, 137.4,
137.8, 146.7, 189.8; MS: m/z 439 (MH+), 437 (MH+).
Anal. Calcd for C24H18Cl2N2O2: C, 65.91; H, 4.15; N,
6.41. Found: C, 65.70; H, 4.09; N, 6.47%.
1,2-Bis-[3-oxo-3-(4-methoxyphenyl)propenylamino]
benzene (3d). Yellow solid in 84% yield, mp ›300˚C; IR
(KBr): 1601, 1624, 1636, 3430 cm–1; 1HNMR (CDCl3): δ
3.83 (s, 6H), 6.07 (d, 2H, J = 7.8 Hz), 6.89 (d, 4H, J =
8.7 Hz), 7.08 - 7.16 (m, 4H), 7.34 (dd, 2H, J = 7.8, 11.4
Hz), 7.92 (d, 4H, J = 8.7 Hz), 12.09 (d, 2H, J = 11.4 Hz);
13CNMR (CDCl3): δ 55.3, 95.2, 113.5, 118.7, 124.9,
129.6, 131.9, 132.1, 145.7, 162.4, 190.2; MS: m/z 429
(MH+).
Anal. Calcd for C26H24N2O4: C, 72.88; H, 5.65; N,
6.54. Found: C, 72.69; H, 5.70; N, 6.48%.
1,2-Bis-[3-oxo-3-(4-nitropheny l)propenylamino]ben
zene (3e). Red solid in 95% yield, mp 90˚C; IR (KBr):
1618, 1719, 3079, 3423 cm–1; 1HNMR (CDCl3): δ 6.03
(d, 2H, J = 7.5 Hz), 6.80-6.88 (m, 2H), 6.98-7.10 (m, 2H),
7.54 (dd, 2H, J = 7.5, 12.3 Hz), 8.04 (d, 4H, J = 9 Hz),
8.27 (d, 4H, J =9 Hz), 12.23 - 12.32 (m, 2H); 13CNMR
(CDCl3): δ 93.2, 117.0, 119.6, 123.1, 125.5, 127.6, 131.1,
136.7, 148.1, 187.4; MS: m/z 457 (M+–1), 458 (M+).
Anal. Calcd for C24H18N4O6: C, 62.88; H, 3.96; N,
12.22. Found: C, 63.10; H, 3.91; N, 12.15%.
4. Conclusions
In conclusion, we have developed facile environment-
friendly strategy for the synthesis of hitherto unknown
bis-enaminones from 3-(dimethylamino)-1-phenylprop-
2-en-1-ones. Mild reaction conditions, easy work-up,
excellent yields and water being used as solvent make
this protocol very useful.
5. Acknowledgements
The authors wish to thank the Principal, Rev. Fr. Ioannis
Warpakma, SDB for the facilities and Rev. Fr. Stephen
Mavely, SDB and Rev. Fr. Joseph Nellanatt, SDB for
their encouragement during the course of this investiga-
tion. The financial support from UGC-New Delhi is
gratefully acknowledged. ASD thanks the UGC for pro-
ject fellowship. Thanks are also due to the Heads of
RSIC-CDRI (Lucknow) and RSIC-NEHU (Shillong) for
recording spectra.
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