General solvent-free ionic liquid catalyzed C-N/C-C coupled cyclization to diverse dihydropyrimidinones and new organic materials: Langmuir-Blodgett film study

Article abstract of DOI:10.1039/c5ra01618e

An ionic liquid catalyzed dual C-N/C-C coupled cyclization of a three component assembly is demonstrated to access 3,4-dihydropyrimidin-2(1H)-one (DHPM) analogues under solvent-free green conditions. Innovative new organic materials are introduced with pu

Full text of DOI:10.1039/c5ra01618e

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General solvent-free ionic liquid catalyzed C–N/
C–C coupled cyclization to diverse
Cite this: RSC Adv., 2015, 5, 24681
dihydropyrimidinones and new organic materials:
Langmuir–Blodgett film study†
Received 27th January 2015
Accepted 27th February 2015
a
a
b
a
a
Swapan Majumdar,* Jhinuk De, Ajitesh Pal, Indra Ghosh, Ranendu K. Nath,
DOI: 10.1039/c5ra01618e
c
d
d
Sandip Chowdhury, Dipanwita Roy and Dilip K. Maiti*
www.rsc.org/advances
8
c
An ionic liquid catalyzed dual C–N/C–C coupled cyclization of a three syntheses into the nonhazardous multi-component strategy
7–10
component assembly is demonstrated to access 3,4-dihydropyr- towards green synthesis
of functional molecules through
imidin-2(1H)-one (DHPM) analogues under solvent-free green development of solvent-free non-metallic processes such as
conditions. Innovative new organic materials are introduced with pure using ionic liquid (IL) as a green solvent cum catalyst, which
and mixed DHPM using LB high surface pressure, AFM and photo- found scant application. Recent medicinal research found
8a
9,10
10
physical studies.
DHPMs as active pharmaceutical agents for epilepsy (A, Fig. 1),
antihypertensive calcium ion channel blocker (B), prostatic
hyperplasia (C), cancer (D), fungal, viral, bacterial, inamma-
Organic compounds possessing aggregation properties have
attracted the attention of research, fabrication, production and
business communities as futuristic materials for next genera-
tion electronic devices. Organic molecules are quite innovative
components for designing materials for high-tech devices of
ultimate sensitivity because of their structural diversity leading
to much improved semiconducting, conducting, non-
conducting, photoluminescence, storage and display perfor-
mances relative to silicon, copper and other traditional ingre-
6,11,12
tory and cardiovascular diseases.
The syntheses of valuable
11
DHPMs were achieved by Biginelli and Biginelli-type coupling
of aldehyde, urea/thiourea and b-dicarbonyl compounds using
mineral acids, Lewis acid catalysts, nanoparticles, IL, solvent-
12
free and/or catalyst-free conditions.
Hitherto, all these methodologies come up with drawbacks
using volatile organic solvents, excess quantity of IL, exhaustive
usage of energy sources (e.g. high temperature), prolong reac-
tion time, tedious catalyst preparation and isolation, formation
of inevitable side products, and/or insufficient yield. With these
1–5
dients. They are also lighter, more exible, non-magnetic,
biodegradable and inexpensive with respect to their inorganic
counterparts. Benzimidazoles, imidazoles, porphyrins, and
other N-heterocycles are utilized as the main building blocks for
difficulties in mind we developed a general solvent-free C–N/C–
13
C
coupled fundamental annulation process
to DHPM
analogues (Scheme 1) using protic ionic liquid as a catalyst. The
preliminary results on LB study, aggregation property and
surface morphology of the rst ever DHPM-based materials are
reported.
2
organic electronics. Introducing an ubiquitous framework
6
dihydropyrimidinone (DHPM) -bearing several nanoscale
2b
gluing interactions (E, Fig. 1) into the active research area is
desirable to achieve new organic materials for fabricating
innovative devices. With the current global awareness of
developing environment friendly green industrial technolo-
We decided to begin with an easily affordable protic IL
catalyst such as imidazolium triuoroacetate derivatives for
developing a solvent-free green cyclization strategy of a three
7
gies, it is urgent to divert our attention from multistep organic
1
component assembly comprising benzaldehyde (R ¼ Ph, 1a,
2
Scheme 1), urea (X ¼ O, 2a) and ethyl acetoacetate (R ¼ OEt, 3a)
to afford the desired DHPM (4a) and the successful annulation
approach will be generalized and diversied through direct
synthesis of varied functionalized and chiral DHPMs, their thio
analogues and also the designed DHPMs of potential material
properties (E, Fig. 1). Gratifyingly aer a limited number of
attempts we found rapid (30 min, entry 1, Table 1) conversion
a
Department of Chemistry, Tripura University, Suryamaninagar 799 022, India.
E-mail: smajumdar@tripurauniv.in; Fax: +91-381-2374802; Tel: +91-381-2379070
b
State Forensic Science Laboratory, Narsingarh, Agartala 799 015, India
c
Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700 032,
India
d
Department of Chemistry, University of Calcutta, University College of Science, 92, A.
P. C. Road, Kolkata-700 009, India. E-mail: dkmchem@caluniv.ac.in; Fax: +91-33- (100%) of the ingredients into the desired product 4a (entry 1) at
2
†
1
351-9755; Tel: +91-33-2350-9937
ꢀ
moderate temperature (70 C) using 10 mol% of PIL, 2-methyl-1-
Electronic supplementary information (ESI) available. See DOI:
0.1039/c5ra01618e
butyl imidazolium triuoroacetate (I, Scheme 1). Interestingly
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Fig. 1 Medicinally significant and potential material DHPMs.
Scheme 1 A rapid C–N/C–C coupled annulation strategy to DHPMs.
progress of the reaction was ascertained simply by watching and thione analogues (5a–e). To our delight the outstanding
slow deposition of the solid product, which started within a stereo-selection ability of the non-metallic PIL catalyst was
couple of minutes. Comparable yield (89%) was obtained on observed to furnish optically pure single diastereomer 4u from
reduction of catalyst loading from 10 to 5 mol% (entry 2). structurally rigid chiral sugar aldehyde. Absolute stereochem-
However the yield was reduced (entries 3 and 4) on further istry (4u) was determined by NMR spectroscopic analysis (ESI†).
decrease of IL concentration (4–1 mol%), and no product was In general, the reactions are very clean, generate no by product
detected in absence of IL, heat or using Bu
entries 5–8). A plot for PIL (I) concentration vs. conversion of with water and require no chromatographic separation.
the starting material is included in the ESI.† However other However, poor solubility of urea hampered the precipitation
ionic liquid such as BMImBF and BMImPF (ref. 9b) produ- process of the product leading to formation of impure material
cedthe desired product with moderate yield (52–56%; entries in few reactions. On dissolving urea in a little amount of water
and 10) at high temperature. Thus, the results showed in (0.5 mL) solved the problem without changing the reaction rate
4
NBr and BMImCl except water, furnish highly pure products aer simple washing
(
4
6
9
Table 1 indicated that protic ionic liquid (I) offers best results and yield. Alternatively crystallization in ethanol can be used to
than the other ionic liquid. We speculate that this is due to afford pure DHPM. The designed DHPM-bearing ester, long-
1
1c,d
capability of protic ionic liquid I to activate carbonyl group
chain alkoxy, donor HN–CO–NH, p-bond and aromatic moiety
of aldehydes which speeds up the iminium ion (X) formation (4v) and its thio analogue (5f) were achieved under similar
with urea or thiourea and subsequent nucleophilic addition conditions.
to the protic ionic liquid activated enolized-b-keto ester fol-
We investigated the aggregation behaviour of 4v by using
3
lowed by cyclization (Z) and elimination of water results the LB technique because it can efficiently be used for making
expected DHPM (Scheme 2). Lacking of proton in other ionic lms of controllable thickness, uniform surface and a high
liquids, carbonyls of aldehydes/b-dicarbonyls either not or degree of orientational order of pure 4v and mixed DHPM–
less efficiently activated thus they required high temperature arachidic acid (AA). The mixed monolayers with AA was
and long reaction time. attempted for examining the valuable monolayer stability,
3
e
The scope and versatility of the green strategy was success- second harmonic generation effects, pyroelectric, photo-
fully examined with a wide range of precursors towards rapid chromic and intermolecular interactive properties. In our
(
10–90 min) access to functionalized DHPMs (4b–s, Fig. 2) with experiments, we observed that on spreading out of a dilute
ꢂ3
excellent yield (84–99%). A broad range of DHPMs possessing solution of pure 4v in chloroform (2 ꢁ 10 M) onto a pure
electron donating and electron withdrawing functionality water surface and compressing slowly resulted an initial rise
ꢂ1
substituted phenyl (4b–l), naphthyl (4m), conjugated p-bond of isotherm from zero to about 25 mN m (Fig. 3A). A kink
ꢂ1
(4n), and aliphatic substituents (4o–q) were synthesized. Acetyl was observed and enhanced sharply to 55 mN m . The
acetone, exible chiral aldehyde and thiourea were also surface pressure versus area per molecule (p–A) isotherms of
smoothly underwent for the dual C–N/C–C coupling process to pure AA and 4v–AA mixed monolayers were executed (Fig. 3B)
furnish corresponding DHPMs possessing acetyl group (4r and at the air–water interface. The abscissas of these gures rep-
4s), chiral amine-based 4t with about 3 : 1 diastereomer ratio resented the area of Langmuir lm divided by the total
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a
Table 1 Optimization for synthesis of DHPM (4a)
of 4v in the mixed monolayer between the AA molecules. Thus
the DHPM molecules didn't penetrate into the fatty acid
monolayer, rather are located underneath the head groups of
the densely packed AA monolayer at higher surface pressures.
Determination of miscibility in the LB monolayer is very
important to understand the basic interactions involved in
the DHPM and AA molecules, which are responsible for the
stability of the monolayer at the air–water interface. To
analyze the degree of miscibility and thermodynamic nature
of mixing of the binary components in the mixed LB, we
examined the average area per molecule as a function of the
b
Catalyst
Entry (mol%)
Temperature Time
Conversion Yield
(%)
ꢀ
( C)
(min)
(%)
1
2
3
4
5
6
7
8
9
1
I (10)
I (5)
I (1)
I (4)
None
I (5)
70
70
70
70
70
30
30
100
100
60
90
—
—
—
—
90
89
40
81
0
0
0
0
56
52
300
300
300
300
30
30
60
60
30
c
Bu
4
NBr
100
100
c
BMImCl
BMImBF
BMImPF
c
d
4
100
100
90
80

lm composition at different surface pressures (5, 10, 20, 30,
c
d
0
6
ꢂ1
4
0 and 45 mN m , Fig. 3B). The nature of molecular inter-
a
b
c
d
ꢀ
1
0 mmol scale. Isolated yield. 10 mol%. No reaction at 70 C.
actions and also miscibility of the two components were
examined by the quantitative analysis of the excess area (A ) of
The excess
E
1
4a,b
the mixed monolayer at the air–water interface.
area was obtained by comparing the experimentally observed
average area per molecule (A ) of a mixed monolayer con-
1
2
sisting of components 1 and 2 with that of an ideal mixed
monolayer (Aideal):
A
ideal ¼ A
1
N
1
+ A
2
N
2
(1)
where, Aideal is the ideal area per molecule, N and N are the
1
2
mole fractions of the constituent molecules of the mixed
monolayer, A and A are the area per molecule of single
1
2
component at a xed surface pressure. The deviation from the
ideal behaviour found by computing the excess area of mixing,
A ¼ A ꢂ Aideal
(2)
E
12
1
4a,c
A
E
should be zero in the ideal situation.
Our 4v–AA mixed
Scheme 2 PIL (I) catalytic cycle for synthesis of DHPMs.
monolayer LB lms showed positive deviation from the ideal
behaviour at all compositions of the mixtures (Fig. 3B). The
results indicate the miscible nature and having repulsive type
of interactions between DHPM (4v) and AA molecules. The
area occupied by the (4v–AA) mixed monolayer at a particular
surface pressure was greater than the area occupied by the
same amount of the pure components, which also supported
existence of repulsive interaction between them. The cohesive
forces between like molecules 4v–4v and AA–AA dominated in
the mixed lms with respect to the adhesive force between the
unlike components (4v–AA) resulting to a partial or total
phase separation. It led to formation of aggregated micro-
structure of 4v in the mixed lms. The photophysical stud-
number of the molecules, N ¼ NEMT + NAA, where N4v and NAA
are the numbers of 4v and AA molecules respectively. The pure
AA isotherm was consistent with the behaviour expected from
the previous measurements of this system. The isotherm of
2
pure AA was resulted the limiting area of 0.20 nm indicating
vertical standing of the long-chain fatty acids on water. The
isotherm of pure 4v is very different to that of AA and no kink
was observed. On mixing 4v with AA, the DHPM inserted into
the monolayer, which was conrmed by changing in the li
off point and the existence of kink point in the mixed
ꢂ1
isotherm at about 25 mN m . The p–A isotherms of the 4v–AA
2
b,5
ies
of the 4v–AA mixed, microcrystal and pure 4v lms
mixed monolayer showed that the area/molecule enhanced
with increasing mole fraction of 4v due to strong interaction
between 4v–AA. The isotherms of the mixed lms were
resulted a shape that practically corresponds to the combi-
nation of those of individual components with small differ-
ences. The isotherms originated prominent kink points at
higher mole fractions of 4v (0.7, 0.8, 0.9), which corresponded
well with that of 4v. However, this kink point is practically
absent at lower mole fractions of 4v (0.1, 0.3 and 0.5), which
was similar to pure AA. Another noticeable feature of the
isotherms of 4v–AA mixed mono-layers is that the isotherms
did not converge at higher surface pressures suggesting retain
showed red-shied and broadened UV-vis spectra (Fig. 3C) in
comparison with the pure 4v in solution (277 nm). The
broadening of the spectrum along with the red-shi might be
due to formation of J-type of aggregates in the mixed (4v–AA)
LB lms, pure and microcrystal lms of 4v–AA. Interestingly
packing pattern of molecules did alter on increasing the mole
fraction (0.3, 0.5 and 0.8), which is an important phenomena
for technical application of the material. The change in
intensity might be due to the change of packing density of 4v
molecules in the mixed LB lms. The emission spectrum of 4v
solution (Fig. 3D) showed a peak at 526 nm and a distinct
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Fig. 2 Synthesized diverse DHPM analogues.
band at 373 nm. The spectra of pure 4v, microcrystal and (panel G, Fig. 3), which is an outstanding new observation. The
mixed lm were blue shied, which were due to a specic AFM image of 4v–AA mixed LB lm (panel H, Fig. 3) established
orientation and closer association of 4v in the pure and mixed the capability of the DHPM to aggregate with other component

lms.
The AFM imaging of LB monolayer of AA exhibited forma- which has tremendous application during fabrication of
tion of an aggregated nanowire (panel E, Fig. 3). Similarly, the organic electronic devices.
leading to construction of organic nanostructures materials,
4
surface morphology of the pure DHPM (4v) monolayer trans-
ferred at 25 mN m revealed formation of spherical aggregated general, IL catalyzed dual C–N/C–C coupled-annulation
In conclusion, we have demonstrated a solvent-free,
ꢂ1
material of about 100 nm dimension (panel F, Fig. 3). On strategy featuring operational simplicity, atom and energy
ꢂ1
enhancement of surface pressure to 40 mN m changed the efficiency, environmental safety, high conversion, fast reac-
packing density of the 4v monolayer lm leading to fabrication tion rate, excellent yield, and tolerance of functionalities and
of grainy microstructure having a higher density domains chirality to afford diverse DHPMs, their chiral and marcapto
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Fig. 3 (A) Surface pressure (p) vs. area per molecule (A) isotherms of mixed monolayers of DHPM (4v) and AA at different mole fractions of 4v
along with pure AA and 4v. (B) Plot of area/molecule versus mole fraction for mixed DHPM (4v)–AA monolayers on water sub-phase at various
surface pressures. (C) UV-vis absorption spectra of DHPM CHCl solution (SOL), pure film of 4v microcrystal (MC) and 4v–AA mixed LB film at
3
three different mole fractions namely, 0.3, 0.5, 0.8. (D) Emission spectra of DHPM (4v) in solution (SOL), 4v (pure), microcrystal (MC) and 4y/AA
ꢂ1
mixed LB film at a mole fraction of 0.5. (E) Atomic force microscope image of monolayer of AA, (F) pure film of DHPM 4v at 25 mN m , (G) pure
ꢂ1
film of DHPM 4v at 40 mN m , (H) mixed LB film of 4v–AA.
analogues. In addition, the UV-vis, uorescence and AFM
studies of pure and mixed thin lms of the ubiquitous DHPM
Acknowledgements
to innovative futuristic materials for organic electronics, and The authors gratefully acknowledge the nancial grants of DST
LB high surface pressure controlled development of (no. SR/S1/OC-49/2010 and SR/NM/NS-29/2010) and CSIR (SRF),
outstanding aggregation property will nd valuable applica- Govt. of India and also instrumental support from CRNN, CU.
tion in chemical, material and medical sciences.
We are thankful to Mr Shantanu Chakraborty of our Dept. of
Physics, TU for capturing AFM images.
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