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Visible light promoted synthesis of dihydropyrano-

[2,3-c]chromenes via a multicomponent-tandem
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Cite this: Green Chem., 2016, 18,

3221
Received 30th November 2015,
Accepted 25th March 2016
DOI: 10.1039/c5gc02855h
www.rsc.org/greenchem
strategy under solvent and catalyst free
conditions†
Jyoti Tiwari,‡a Mohammad Saquib,‡a Swastika Singh,a Fatima Tufail,a Mandavi Singh,a
Jaya Singhb and Jagdamba Singh*a

The development of unique, mild and efficient one pot, multicom-
ponent-tandem synthesis of highly functionalized dihydropyrano
[2,3-c]chromenes under photochemical activation is reported. The
key feature of the present work is the utilization of visible light
which is a ubiquitous, inexpensive and eco-sustainable reagent for
catalysing the reaction. The reported methodology is the first
example of visible light induced synthesis of dihydropyrano[2,3-c]-
chromenes and includes several advantages like solvent and catalyst
free, environmentally benign reaction conditions, operational sim-
plicity, cost effectiveness, short reaction times, high atom economy,
and excellent yields, making it a genuinely green protocol.
Organic chemists have long aspired to synthesize organic
molecules using visible light, the way plants do. Visible light
can serve as an attractive, sustainable, non-toxic, easy to use
and universally available energy source.1 However it is only in
recent years, with the growing emphasis on the applications of
green principles in organic synthesis, that this idea seemed to
have been explored with seriousness. Consequently, an
increasing number of chemists are experimenting with visible
light driven chemical synthesis as an economically and energe-
tically beneficial, green route for construction of organic
molecules.2
Another thrust area in green chemistry is the development
of solvent free synthesis not only because of the need to elim-
inate the use of toxic organic solvents which are the cause for
the majority of waste and pollution generated by chemical pro-
cesses but also because solvent-free synthesis reduces costs,
requires less energy, leads to faster reaction rates, and a
reduction in reactor size and capital investment.3
a
Environmentally Benign Synthesis Lab, Department of Chemistry, University of
Allahabad, Allahabad-211002, India. E-mail: dr.jdsau@gmail.com;
Tel: +91 9415218507
b
Department of Chemistry, LRPG College, Sahibabad, Ghaziabad-201005, India
† Electronic supplementary information (ESI) available. See DOI: 10.1039/
c5gc02855h
‡ These authors contributed equally.
In recent years multicomponent reactions (MCRs) have
emerged as a powerful new strategy in synthetic organic chem-
istry and drug discovery, allowing access to compounds with
structural complexity and diversity in a single operation, with
improved atom and time economy, simplicity, synthetic
efficiency and a lower number of reactions and purification
steps.4
The pyranochromene motif is present in a wide variety of
natural and synthetic molecules of biological importance.5
Amongst the pyranochromenes, dihydropyrano[2,3-c]chro-
menes form a special sub-class exhibiting diverse biological
activities such as anti-microbial,6 anti-cancer,7 anti-dyslipi-
demic,8 anti-hyperglycemic,9 anti-HIV,10 antioxidant,11 anti-
allergic,12 xanthine oxidase inhibitory,13 acetylcholinesterase
and butyrylcholinesterase inhibitory,14 Src kinase inhibitory
activities,15 etc. (Fig. 1).
It is therefore not surprising that numerous methods for
the synthesis of dihydropyrano[2,3-c]chromenes have been
reported in the literature.16,17
This is especially true for the last few years which have seen
a phenomenal increase in the number of reports on the syn-
thesis of dihydropyrano[2,3-c]chromenes,17 (Fig. 2) which may
in part be due to the increasing recognition of their biological
significance.6,7a,c,13–15,18
Many of these procedures have merits; however they have
drawbacks like the use of expensive catalysts, volatile solvents,
high temperatures, multistep synthesis, long reaction times
and tedious work-up procedures.9,17c,19 Therefore, the develop-
ment of newer, more efficient and environmentally benign
methods for the synthesis of dihydropyrano[2,3-c]chromenes
has become an increasingly vigorous research domain.13,17,18
Consequently, in continuation of our ongoing program on
the green synthesis of biologically important small hetero-
cycles20 we became interested in the development of a new
multicomponent, catalyst free strategy for the synthesis of
pyranochromenes under visible light irradiation.
We initially attempted a three-component condensation of
4-nitrobenzaldehyde (1, 1 mmol), malononitrile (2, 1 mmol)

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Fig. 1 Examples of some dihydropyrano[2,3-c]chromene based bioactive molecules.
Fig. 2 Number of publications containing “dihydropyrano[2,3-c]chro-
menes” as the topic, 1950–present (Source Reaxys).
and 4-hydroxycoumarin (3, 1 mmol) for obtaining pyranochro-
mene using visible light as a promoter under catalyst free
conditions in a variety of green as well as conventional organic
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solvents such as ethanol, glycerol, dichloromethane, ethyl
acetate, tetrahydrofuran, acetonitrile, etc. at room temperature
(RT). No reaction was observed in any of the experiments,
except in the case of ethanol (51%), glycerol (46%) or metha-
nol (43%) as a solvent. The structure of the synthesized dihy-
dropyrano[2,3-c]chromene 421a was confirmed by recording its
1
H NMR, 13C NMR, MS and IR spectra.
In our efforts to increase the yield of the product, we per-
formed the reaction using ethanol/water 1 : 1, leading to a
marginal increase in yield (56%) but no reduction in reaction
time. At this juncture we thought of carrying out this reaction
under solvent free conditions, which led to a noticeable
increase in yield (69%) but no change in reaction time. In all
these experiments (Table 1, entries 5–9) we noticed that a
small amount of the 4-hydroxy coumarin 3 and the benzyli-
dene–malononitrile intermediate I remained unreacted even
after allowing the experiment to run for 24 h (Table 1, entry
10). In order to overcome this problem we used a small excess
of 3 (1.2 mmol) but with no success. A small amount of benzy-
lidene–malononitrile intermediate I remained unreacted as
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Table 1 Initial optimization of the reaction conditionsa

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Entry Solvent Time (h) 1 : 2 : 3 (mmol) Yield of 4 b (%)

1 EtOAc 12 1:1:1 Trace

2 DCM 12 1:1:1 Trace
3 THF 12 1:1:1 Trace
4 Acetonitrile 12 1:1:1 Trace
5 Methanol 12 1:1:1 43
6 Ethanol 12 1:1:1 51
7 Glycerol 12 1:1:1 46
8 Ethanol/water 1 : 1 12 1:1:1 56
9 None 12 1:1:1 69
10 None 24 1:1:1 69
11 None 12 1 : 1 : 1.2 69
12 None 1.3 1 : 1.2 : 1 95
13 None 1.3 1 : 1.5 : 1 95
14 None 1.5 1 : 1.1 : 1 88
15 None 2 1 : 0.6 : 1 50
16 None 12 1.2 : 1 : 1 69
a
All reactions were carried out under visible light irradiation using a 22 W CFL at room temperature under air. b Isolated yields.

before (Table 1, entry 11). We now repeated the experiment
using 1.2 mmol of malononitrile (2). To our surprise this led
to a noticeable increase in yield and a drastic reduction in
reaction time (Table 1, entry 12). A further increase in the
amount of 2 did not produce better results (Table 1, entry 13).
However a reduction in the amount of 2 led to a lowering in
yield and a marginal increase in reaction time (Table 1,
entries 14 and 15).
We now carried out a series of experiments using light of
different intensities (8 W, 15 W, 20 W and 32 W), in order to
identify the optimal intensity of visible light needed for this
reaction. It was observed that the yields and reaction times
were the same when 20 W and 22 W CFLs were used. However,
when CFLs of lower intensities were used, a marginal decrease
in the yield and rate of reaction was observed (Table 2, entries
3 and 4). The use of a CFL of higher wattage (32 W) on the

Table 2 Effect of the visible light intensity on the course of the reactiona

Entry Visible light intensity Time (h) Yield of 4 b (%)

1 22 W (CFL) 1.3 95
2 20 W (CFL) 1.3 95
3 15 W (CFL) 2 91
4 8 W (CFL) 2.5 89
5 32 W (CFL) 1.3 95
a
All reactions were carried out neat, using 1 (1 mmol), 2 (1.2 mmol) and 3 (1 mmol) at room temperature under air. b Isolated yields.

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Table 3 Substrate scopea

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Entry Aldehyde Active methylene Dihydropyrano[2,3c]chromene Time (h) Yieldb (%) Ref.

1 1.8 90 21b

2 1.5 92 19

3 1.7 91 21b

4 1.6 86 23

5 1.7 84 9

6 1.6 88 19

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Table 3 (Contd.)
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Entry Aldehyde Active methylene Dihydropyrano[2,3c]chromene Time (h) Yieldb (%) Ref.

7 1.7 90 21a

8 1.9 89 21b

9 1.5 93 24

10 1.7 90 23

11 1.8 91 21b

12 2.3 88 22

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Table 3 (Contd.)
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Entry Aldehyde Active methylene Dihydropyrano[2,3c]chromene Time (h) Yieldb (%) Ref.

13 2.2 80 9

14 2.3 82 21a

15 1.7 80 9

16 2.5 76 22

17 2.3 88 21a

18 1.8 85 21a

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Table 3 (Contd.)
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Entry Aldehyde Active methylene Dihydropyrano[2,3c]chromene
19
20
a
All reactions were carried out neat, using the respective aldehydes 1, 5–21 (1 mmol), active methylene compound 2 or 22 (1.2 mmol) and
4-hydroxy coumarin (3) (1 mmol) at room temperature under air. b Isolated yields.
other hand did not have any appreciable effect on the yield or
reaction time.
Once ideal conditions for carrying out this reaction had
been identified, the scope and limitations of the developed
synthetic strategy were explored under the optimized reaction
conditions for the synthesis of a series of dihydropyrano[2,3-c]-
chromene derivatives by reacting a variety of aryl and hetero-
aryl aldehydes with malononitrile or ethyl 2-cyanoacetate and
4-hydroxy coumarin (Table 3). It was observed that the use of
aldehydes bearing an electron withdrawing group led to higher
yields and faster reaction while the presence of an electron
donating group on the aldehyde slowed down the reaction and
led to a reduction in the yield of the product (Table 3). Likewise
the use of malononitrile led to much higher yields and faster
reaction rates compared to ethyl 2-cyanoacetate (Table 3).
In order to demonstrate the general applicability of the
above method we now extended it for the construction of other
pyran annulated heterocycles. 1,3-Cyclohexadione (43), dimedone
(44) and barbituric acid (45) were used in place of 4-hydroxy cou-
marin, leading to the formation of 4H-chromenes 46, 47 and
pyrano[2,3-d]pyrimidinone 48 in excellent yields (Table 4).
We conducted a few reactions in order to decipher the
mechanistic pathway (Table 5). When the reaction was con-
ducted in the dark at room temperature the first step pro-
ceeded at a markedly slow rate. TLC after 3 h showed the
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Time (h) Yieldb (%) Ref.
2 80 23
2.1 82 23
formation of the benzylidene–malononitrile intermediate I
with almost 90% utilization of the starting materials. However,
after addition of 4-hydroxy coumarin (3) little further progress
was observed in the reaction, the target compound 4 being iso-
lated in 14% yield after 4 h of stirring. Repeating the above
experiment at 50 °C led to the formation of intermediate I,
with the complete utilization of the starting material, in about
30 minutes. However, no appreciable change was observed in
the course of the reaction in the second step. Moreover, the
second step of the reaction was inhibited on using hydro-
quinone (1.0 mmol), which shows that there may be radical
intermediates involved in this step (Table 5, entry 3). Carrying
out the reaction under an inert, moisture free atmosphere led
to only a slight reduction in yield (88%), which rules out any
role of water or oxygen in the mechanistic pathway.
In light of the experimental observations and literature
reports2c,26,27 we have proposed a plausible mechanistic
pathway for the reaction as depicted in Fig. 3. The first step
appears to be proceeding primarily through mechanochemical
activation although visible light may also be playing a part by
imparting additional energy, speeding up the reaction. In the
second step photochemical activation seems to have a definite
role. It is proposed that visible light activates the benzylidene–
malononitrile intermediate to abstract a methylenic hydrogen
from malononitrile, furnishing a malononitrile radical which
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Table 4 General applicability of the above methoda

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Entry Aldehyde X Y Pyran annulated heterocycle Time (h) Yieldb (%) Ref.

1 CH2 CH2 1.8 90 25b

2 CH2 C(CH3)2 1.5 92 25a

3 NH 1.7 91 25c

a
All reactions were carried out neat, using the respective aldehydes 1 or 15 (1 mmol), malononitrile (2) (1.2 mmol) and the respective CH-acids
43–45 (1 mmol) at room temperature under air. b Isolated yields.

in turn abstracts a hydrogen from 4-hydroxy coumarin, regene-
rating the malononitrile molecule and trigerring a cascade of
reactions finally culminating in the formation of the dihydro-
pyrano[2,3-c]chromene.
To establish the practicability of the disclosed methodology,
we performed the experiment on a gram scale. 4-Nitrobenzal-
dehyde (1) (10 mmol, 1.51 g) was reacted with malononitrile
(2) (10 mmol), followed by the addition of 4-hydroxycoumarin
(3) (10 mmol) to obtain the dihydropyrano[2,3-c]chromene 4
in 93% yield in about 80 minutes. All the reactions including
the scale up reaction were carried out using a household CFL
and common laboratory glassware under air which highlights
the operational simplicity of this method (Scheme 1).
Conclusion
In summary, we have developed a simple, yet highly efficient,
visible light activated, ‘real’ green synthetic strategy to obtain
highly functionalized dihydropyrano[2,3-c]chromenes through
a one pot, multicomponent-tandem approach. To the best of
our knowledge this is the first synthesis of dihydropyrano-

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Table 5 Deciphering the mechanistic pathwaya

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Step 1 Step 2

Entry Reaction conditions and time Remarks Reaction conditions and time Remarks Overall yieldc (%)

1 Dark, RT, 3 h Reaction Dark, RT, 4 h Reaction 14

completeb incomplete
2 Dark, 50 °C, 30 min Reaction Dark, 50 °C, 4 h Reaction 21
complete incomplete
3 CFL (20 W), RT, hydroquinone (1 eq.), Reaction RT, hydroquinone (1 eq.), 4 h Reaction 34
20 min complete incomplete
4 CFL (20 W), RT, N2 atm., anhydrous Reaction RT, N2 atm., anhydrous Reaction 88
conditions, 20 min complete conditions, 1 h complete
a
All reactions were carried out neat, using benzaldehyde 1 (1 mmol), malononitrile (2) (1.2 mmol) and 4-hydroxy coumarin (3) (1 mmol) at room
temperature under air. b 90% utilization of starting materials. c Isolated yields.

Fig. 3 Plausible mechanism.

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Scheme 1 Demonstrating the practicality of the present method.
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chromenes using photochemical activation. Due to the mild
reaction conditions, a wide range of substrates can be toler-
ated. Elimination of solvent and catalyst, short reaction times,
operational simplicity, easy workup procedure, high atom
economy and excellent yields are the other important aspects
of this method.
Acknowledgements
The authors are thankful to SAIF, PU, Chandigarh and SAIF,
CDRI, Lucknow for spectral data. The authors also acknowl-
edge the financial support from UGC, New Delhi in the form
of a major research project (Project No. 42-263/2013 (SR)) and
fellowships for Swastika Singh, Fatima Tufail and Mandavi
Singh. Dr Mohammad Saquib specifically thanks UGC, New
Delhi for Dr D.S. Kothari Postdoctoral Fellowship Award No.
F.4-2/2006 (BSR)/13-1030/2013 (BSR) while Jyoti Tiwari thanks
CSIR, New Delhi for a Junior Research Fellowship.
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