Three-Component synthesis and characterization of nicotinamide derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment

Article abstract of DOI:10.1080/00397911.2018.1515959

The synthesis of nicotinamide derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment through the base-promoted three-component reaction of an aromatic aldehyde, an acetoacetamide and malononitrile dimer in the presence of an oxidant is reported. The HOMO-LUMO energy levels were estimated by cyclic voltammetry and UV-Vis measurements. The influence of aryl and carbomoyl substituents on the optical and electrochemical properties was also investigated.

Full text of DOI:10.1080/00397911.2018.1515959

Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic
Chemistry
ISSN: 0039-7911 (Print) 1532-2432 (Online) Journal homepage: http://www.tandfonline.com/loi/lsyc20
Three-Component synthesis and characterization
of nicotinamide derivatives containing a buta-1,3-
diene-1,1,3-tricarbonitrile fragment
Ivan N. Bardasov, Anastasiya U. Alekseeva, Sergey S. Chunikhin & Oleg V.
Ershov
To cite this article: Ivan N. Bardasov, Anastasiya U. Alekseeva, Sergey S. Chunikhin & Oleg
V. Ershov (2018): Three-Component synthesis and characterization of nicotinamide derivatives
containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment, Synthetic Communications, DOI:
10.1080/00397911.2018.1515959
To link to this article: https://doi.org/10.1080/00397911.2018.1515959
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SYNTHETIC COMMUNICATIONS
https://doi.org/10.1080/00397911.2018.1515959
Three-Component synthesis and characterization of
nicotinamide derivatives containing a buta-1,3-diene-1,1,3-
tricarbonitrile fragment
Ivan N. Bardasov , Anastasiya U. Alekseeva , Sergey S. Chunikhin , and
Oleg V. Ershov
Ulyanov Chuvash State University, Moskovsky pr. 15, Cheboksary, 428015, Russia
ABSTRACT
ARTICLE HISTORY
The synthesis of nicotinamide derivatives containing a buta-1,3-
diene-1,1,3-tricarbonitrile fragment through the base-promoted
three-component reaction of an aromatic aldehyde, an acetoaceta-
mide and malononitrile dimer in the presence of an oxidant is
reported. The HOMO-LUMO energy levels were estimated by cyclic
voltammetry and UV-Vis measurements. The influence of aryl and
carbomoyl substituents on the optical and electrochemical properties
was also investigated.
Received 17 July 2018
KEYWORDS
Cyclic voltammetry;
malononitrile dimer;
multicomponent reaction;
optical properties; TCPy
GRAPHICAL ABSTRACT
Introduction
Nicotinamide derivatives widely occur in various natural products, functional materials,
[
1–15]
and pharmaceutical agents.
Nicotinamide, also known as niacinamide, is a form of
3
[1]
vitamin B and it is essential for the human health. Various nicotinamide derivatives
anti-HIV, and anti-diabetogenic properties. Several nicotina-
mides were used for treating acquired inflammatory,
[
2–6]
[7]
[8]
possess antitumor,
[
9,10]
[11–13]
heart
and
[
14,15]
skin
diseases.
At the same time, the spectral-luminescent properties of nicotinamides and their
complexes have not been studied practically. Although the presence of an amide group
in the beta position of substituted heterocyclic compounds favored the appearance of
[
16–19]
optical properties.
A convenient approach to the synthesis of highly functionalized nicotinamides is the
[
20–22]
use of multicomponent reactions (MCR).
Herein, we report a three-component
synthesis of nicotinamide derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile
CONTACT Ivan N. Bardasov
bardasov.chem@mail.ru
Ulyanov Chuvash State University, Moskovsky pr. 15,
Cheboksary 428015, Russia.
Supplemental data for this article can be accessed on the publisher’s website.
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.
ß 2018 Taylor & Francis Group, LLC

2
I. N. BARDASOV ET AL.
Scheme 1. Synthesis of 4-aryl-5-cyano-6-(dicyanomethylene)-2-methyl-1,6-dihydropyridine-3-carboxa-
mides 1a–i.
(
BDTC) fragment. The importance of this fragment is that it acts as a powerful acceptor
[
23–27]
in push-pool chromophores and compounds with practically useful properties.
Results and discussion
The synthesis of 4-aryl-5-cyano-6-(dicyanomethylene)-2-methyl-1,6-dihydropyridine-3-
carboxamides 1 (TCPy) is based on the three-component reaction between an acetoace-
tamide, an aromatic aldehyde and malononitrile dimer in the presence of sodium nitrite
working as a base as well as an oxidant (Scheme 1).
Various organic bases (piperidine, DABCO, ammonium acetate, sodium ethoxide and
potassium tert-butoxide) were tested and they led to the isolation of the mixture of
compounds 1 and 2. Prolonged heating at reflux with air bubbling also did not ensure
a complete reaction. The isolation of compounds 2 with a subsequent oxidation step
significantly decreased the yield of compounds 1. It was found that the use of sodium
nitrite as a catalyst led to the formation of compounds 1 with good yields of up to 84%.
[
28]
Apparently, sodium nitrite works as the basic catalyst as well as the oxidant.
The reaction includes the tandem Knoevenagel condensation–Michael addition steps,
which lead to the formation of intermediate ff (Scheme 1). Subsequent cyclization of
the amino group to the carbonyl group led to the formation of hexahydropyridine
derivatives B. Elimination of water forms 3-cyano-2-(dicyanomethylene)-1,2,3,4-tetra-
hydropyridines 2 and the further oxidation results in the pyridines 1 with
60–84% yield.
TCPy 1 are yellow or orange crystalline powders and were found to be fluorescent
both in the solution and the solid state. Using compound 1 b as a model the solvato-
chromic properties were investigated (Table 1). It was observed that the maxima of
emission and absorption bands were almost constant in most of the solvents. The only
exception is the “blue shift” of the fluorescence maximum in acetic acid. The most
intensive emission was observed in acetonitrile and DMSO solutions.
Furthermore, the spectral-luminescent properties of compounds 1 with various aryl
and carbomoyl substituents were studied using acetonitrile as the solvent (Fig. 1,

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3
Table 1. Solvatochromic properties of compound 1b.
abs
abs
e (mol ꢁ Lꢂ1ꢁcmꢂ1
flu
Solvent
k
max
(nm)
A
max
)
k
max (nm)
CH CN
3
326, 398
327, 414
328
0.3183, 0.0327
0.4403, 0.0766
0.4488
31965, 3284
40846, 7106
65407
513
413
509
516
507
AcOH
DMSO
AcOEt
328, 429
0.7455, 0.1248
70102, 11735
1
,4-Dioxane
325
0.0813
7508
Figure 1. Absorption spectra of compounds 1a-i in acetonitrile.
Table 2. Absorption and fluorescent properties of compounds 1.
max
max
e (mol ꢁ Lꢂ1ꢁcmꢂ1
max
1
2
max
flu
1
Compound
k
abs
(nm)
A
abs
)
k1flu
(nm)
k
(nm)
1
1
1
1
1
1
1
1
1
1
a
b
c
d
e
f
g
h
i
325, 389
326, 398
325
0.4379, 0.0491
0.3183, 0.0327
0.2143
39894, 4473
31965, 3284
20430
519
528
513
509
–
518
516
517
523
521
511
536
545
522
535
525
518
516
325
0.4935
48731
328, 389
327, 396
325, 382
327, 386
329, 386
0.4688, 0.0721
0.4111, 0.0636
0.1823, 0.0157
0.4759, 0.0487
0.4255, 0.0483
44733, 6880
42178, 6525
15991, 1377
47969, 4909
42663, 4843
1
max
2
max
k
flu
– fluorescence maximum in acetonitrile, excited at 325 nm; k flu
– solid-state emission maximum of com-
pounds 1, excited at 365 nm.
Table 1). Two peaks characterize the absorption spectra: an intense band at 325–329 nm
ꢀ
and a broad band with low intensity at 382–398 nm, presumably corresponding to p–p
and n–p electronic transitions, respectively.
ꢀ
A fluorescence study showed that the most intense fluorescence is observed for com-
pounds 1b,c,e,f with halo- and methoxy-groups. In contrast, for the nitro-substituted
compound 1d the fluorescence was practically not observed. The substituents in the car-
boxamide group of compounds 1h,i had literally no influence on the spectral properties.
The solid-state emission of compounds 1 is in the range of 511–545 nm (Table 2).

4
I. N. BARDASOV ET AL.
Table 3. Electrochemical characteristics of compounds 1, obtained by using cyclic voltammetry and electronic
spectroscopy.
HOMO (eV)
LUMO (eV)
g
E (eV)
onset
onset
Compound
E
ox
vs. Ag/AgCl (V)
found
calc.
found
calc.
found
calc.
k
abs
(nm)
1
1
1
1
1
1
1
1
1
a
b
c
d
e
f
g
h
i
0.713
0.688
0.690
0.750
0.732
0.738
0.712
0.692
0.738
ꢂ5.06
ꢂ5.04
ꢂ5.04
ꢂ5.10
ꢂ5.08
ꢂ5.09
ꢂ5.06
ꢂ5.04
ꢂ5.09
ꢂ6.29
ꢂ6.19
ꢂ6.16
ꢂ6.74
ꢂ6.36
ꢂ6.35
ꢂ6.23
ꢂ6.12
ꢂ6.25
ꢂ2.32
ꢂ2.27
ꢂ2.18
ꢂ2.42
ꢂ2.31
ꢂ2.33
ꢂ2.32
ꢂ2.31
ꢂ2.30
ꢂ3.11
ꢂ2.99
ꢂ2.91
ꢂ4.31
ꢂ3.19
ꢂ3.15
ꢂ3.04
ꢂ3.02
ꢂ3.11
2.74
2.77
2.86
2.68
2.77
2.76
2.74
2.73
2.79
3.18
3.2
3.25
2.43
3.17
3.2
3.19
3.1
3.14
452
447
433
463
448
449
453
453
444
The HOMO energy levels of compound 1 were estimated from the onset oxidation
onset
potential (Eox
) (Table 3). Cyclic voltammetry (CV) was performed in acetonitrile
solution containing 0.1 M tetrabutylammonium hexafluorophosphate (NBu PF ) as
4
6
supporting electrolyte. All potentials have been calibrated with ferrocene/ferrocenium
þ
(
Fc/Fc ) couple as the internal standard and are reported versus saturated silver
chloride electrode (Ag/AgCl). The CV of the compounds 1 shows a reversible oxida-
tion process with the onset points of oxidation in the 0.692–0.750 V region. The
width of the band gap (E ) was refined using electronic spectra of compound 1. The
g
energy of the LUMO was found from the values of HOMO and E because of the
g
irreversibility of the reduction process. It was found that all the compounds synthe-
sized had a small band gap (E ) of 2.68–2.86 eV, and their LUMO energies were in
g
the range from ꢂ2.42 to ꢂ2.18 eV, which is higher than the edge of the conduction
band of titanium dioxide (ꢂ4.4 eV). This indicates the possibility of an efficient elec-
tron transfer from the HOMO of a dye to the conduction band of the
semiconductor.
Figure 2 shows the computational calculations to expect the HOMO/LUMO energy
potentials of compound 1a. The computational theoretical calculation was carried out
using TDDFT(B3LYP)/6-31 þ G(d,p). It showed that electron density of the highest
occupied molecular orbital (HOMO) is localized on the dicyanomethylene moiety and
the lowest unoccupied molecular orbital (LUMO) involved pyridine and phenyl ring
(Fig. 2). Table 3 shows the HOMO/LUMO energy levels for the compounds 1, where
the potential energy values for the computationally calculated levels and the determined
levels are shown. For each compounds, the potential energy levels showed the similar
characteristic patterns from the values of computational calculation and electrochemical
measurement.
It was found that all the compounds synthesized have a small band gap (E ) of
g
2
.68–2.86 eV, and their LUMO energies are in the range from ꢂ2.18 to ꢂ2.42 eV, which
is higher than the edge of the conduction band of titanium dioxide (ꢂ4.4 eV). This
indicates the possibility of an efficient electron transfer from the HOMO of a dye to the
conduction band of the semiconductor. Moreover, the oxidation potentials of the test
compounds were higher than the standard redox potential of the couple triiodide/iodide
in acetonitrile, which demonstrates the possibility of dye regeneration by the electrolyte
solution containing this redox couple.

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SYNTHETIC COMMUNICATIONS
5
Figure 2. HOMO–1, HOMO, LUMO and LUMO þ1 for compound 1a, computed with TDDFT(B3LYP)/
-31 þ G(d,p).
6
Conclusions
Thus, several pyridine derivatives 1 containing the buta-1,3-diene-1,1,3-tricarbonitrile
(BDTC) fragment have been synthesized by the one-pot reaction between an aromatic
aldehyde, an acetoacetamide and malononitrile dimer in the presence of sodium nitrite
working as a base as well as an oxidant. Compounds 1 are yellow or orange crystalline
powders and were found to be fluorescent, both in the solution and the solid state.
Also, HOMO, LUMO levels and energy band gap of synthesized compounds were esti-
mated by the combination of cyclic voltammetry and UV-Vis measurements.
Experimental
The progress of the reactions as well as purity of compounds was monitored by TLC
with F254 silica-gel precoated sheets (Sorbfil, Russia) using ethyl acetate as eluent (spots
were visualized under UV light, by treatment with iodine vapor, or by heating). The
melting points were measured on an OptiMelt MPA100 (Stanford Research Systems,
USA) melting point apparatus. IR spectra were recorded on an FSM-1202 spectrometer
with Fourier transform (Infraspek, Russia) from samples dispersed in mineral oil. The
NMR spectra were recorded on Bruker DRX-500 spectrometers (Bruker Corporation,
Germany) using DMSO-d as solvent and TMS as internal standard, chemical shifts are
6
expressed in ppm. Elemental analysis was performed on a Carlo–Erba model EA1108
(Isomass Scientific Inc., Canada) and the values are ±0.4% of the theoretical ones. Mass
spectra were recorded on a Finnigan MAT INCOS-50 (EI, 70 eV) (GenTech Scientific,
Inc., USA). The UV spectra were recorded on an SF-2000 spectrophotometer (OKB
Spectr, Russia). Fluorescence spectra were recorded on a FluoratVR -02-Panorama spec-
trofluorimeter (Lumex, Russia). Solid-state emission was registered in powders at room
temperature on the Cary Eclipse fluorescence spectrophotometer (Agilent, USA). The
electrochemical measurements were carried out using a Keithley 2450-EC Graphical
Potentiostat (Tektronix, USA) and a voltammetric three-electrode VC-2 cell (working
electrode – platinum, reference electrode – silver chloride, auxiliary electrode
–
platinum).

6
I. N. BARDASOV ET AL.
General procedure for the synthesis of a series of 4-aryl-5-cyano-6-
dicyanomethylene)-2-methyl-1,6-dihydropyridine-3-carboxamides 1
(
A mixture of aromatic aldehydes (1 mmol), acetoacetamide (1 mmol), malononitrile
ꢃ
dimer (1 mmol) and sodium nitrite (1.1 mmol) in EtOH (5 mL) was stirred at 70 C for
6
h. After reaction completion (TLC), the solution was neutralized with 1% HCl to
pH ¼ 4. The precipitate was triturated with H O (10 mL), filtered and washed with H O
2
2
(10 mL), and then recrystallized from a mixture of 1,4-dioxane: i-PrOH.
5
-Cyano-6-(dicyanomethylene)-4-(4-methoxyphenyl)-2-methyl-1,6-dihydropyridine-3-
carboxamide 1b
ꢃ
1
mp 269-270 C (dec.); H NMR (500.13 MHz, DMSO-d ): d 2.42 (3H, s, CH ), 3.80 (3H,
6
3
s, OCH ), 4.08 (1H, br s, NH), 7.01 (2H, d, J ¼ 8.8 Hz, C H ), 7.32 (2H, d, J ¼ 8.7 Hz,
3
6
4
1
3
C H ), 7.37 (1H, NH ), 7.59 (1H, NH ). C NMR (125.76 MHz, DMSO-d ): d 19.28,
6
4
2
2
6
4
1
0.57, 55.15, 96.84, 113.57, 114.21, 118.21, 124.59, 126.64, 129.91, 152.49, 154.50, 156.69,
ꢂ1
60.27, 165.96. IR (mineral oil, cm ): 3388-3107 (NH , NH), 2226, 2199 (CN), 1659
2
þ
(C=O), 1603 (C ¼ C). MS (EI, 70 eV): m/z (%) 331 [M] (15). Anal. Calcd for
C H N O : C, 65.25; H, 3.95; N, 21.14. Found: C, 65.41; H, 4.11; N, 20.98.
1
8
13 5 2
Funding
The research was performed under the financial support of the Russian Science Foundation
grant no. 17-13-01237.
(
ORCID
Ivan N. Bardasov
http://orcid.org/0000-0002-5843-3381
Anastasiya U. Alekseeva
Sergey S. Chunikhin
http://orcid.org/0000-0001-5607-6969
http://orcid.org/0000-0002-9130-5349
Oleg V. Ershov
http://orcid.org/0000-0002-0938-4659
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2
[
[
[
[
[
a
2
3
^
^
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