Green approach to synthesis of novel and broad-range diversity of 4-(aryl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine derivatives

Article abstract of DOI:10.1007/s11164-018-3552-4

Abstract: One-pot, three-component condensation reaction between (phenylsulfonyl)acetonitrile, aromatic aldehydes, and α-naphthol for preparation of 4-(aryl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine derivatives has been reported. The method involves

Full text of DOI:10.1007/s11164-018-3552-4

Research on Chemical Intermediates
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Green approach to synthesis of novel and broad-range
diversity of 4-(aryl)-3-(phenylsulfonyl)-4H-
benzo[h]chromen-2-amine derivatives
Abdollah Morshedi1 Hamid Reza Shaterian1
•
Received: 5 May 2018 / Accepted: 9 August 2018
Ó Springer Nature B.V. 2018
Abstract
One-pot, three-component condensation reaction between (phenylsulfonyl)acetoni-
trile, aromatic aldehydes, and a-naphthol for preparation of 4-(aryl)-3-(phenylsul-
fonyl)-4H-benzo[h]chromen-2-amine derivatives has been reported. The method
involves domino Knoevenagel condensation/Michael addition, and cyclization
cascade. The reaction was performed in glycerol, which is a commercially available,
inexpensive and non-toxic compound. High purity of the products, very high yields
and wide scope of substrates are advantages of this protocol.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11164-
018-3552-4) contains supplementary material, which is available to authorized users.
&
Hamid Reza Shaterian
hrshaterian@chem.usb.ac.ir
1
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan,
PO Box 98135-674, Zahedan, Iran
123

A. Morshedi, H. R. Shaterian
Graphical abstract
Keywords 4-(Aryl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine
(Phenylsulfonyl)acetonitrile Á Glycerol Á Green chemistry Á Multi-component
reactions
Á
Introduction
Green chemistry is a novel technique of looking at organic molecules to design
drugs for pharmaceutical companies [1]. Green, environmentally benign processes
offer several important economic advantages over traditional synthetic protocols,
conveying high energy, hazardous, and wasteful processes towards the ‘‘ideal
synthesis’’ that more useful for the economy, environment and society [2–4].
Multi-component reactions (MCRs) are a green approach towards the synthesis
of various organic compounds, and for researchers there is a lot of scope to develop
varieties of novel multi-component reactions used to synthesize diverse heterocy-
cles, which is a key nucleus for different beneficial drugs [5, 6].
The design of novel and interesting materials with significant biological and
pharmaceutical properties is a main target in medicine and drug design research
[7, 8]. Chromene compounds represent an attractive medicinal scaffold in drug
replacement systems [9–13]. These molecules and their analogs can exhibit
significant effects such as antitumor [14], antimicrobial [15], antifungal [16],
anticoagulant [17], anti-HIV [18], and anti-inflammatory activities [19]. Lipophilic
characters of this class of compounds facilitate their delivery into the cell membrane
123

Green approach to synthesis of novel and broad…
[20]. Benzo[h]chromenes were designed, synthesized, and evaluated for cytotoxic
activity and also exhibited promising cell growth inhibitory activity with ED50
values of 0.01–5.8 lM against all tested tumor cell lines [21]. They showed
antitumor activity against a broad range of cancer cell lines with ED50 values of
0.01–76 lM [21]. Chromenes and their derivatives have been synthesized using
various approaches, including multi-component reactions (MCRs) green synthesis
routes using various techniques [22]. However, most of these methods suffer from
such drawbacks as low yields, long reaction times, harsh reaction conditions,
tedious work-up procedures, tedious steps for the preparation of catalyst, application
of toxic and expensive catalysts, application of hazardous solvents for the work-up
and lack of generality. Moreover, in most of the reported methods, catalysts are not
recyclable. In this backdrop glycerol has emerged as an attractive solvent. It
possesses the benefits of both water and ionic liquids like low toxicity, relatively
low vapor pressure, easy availability, reusability, inexpensiveness, renewability,
high boiling point and ability to dissolve a wide range of organic and inorganic
compounds [23–26]. Development of catalyst-free reactions is another area that has
attracted much attention in green chemistry due to the inherent advantages involved
in terms of cost and environment [27, 28]. Literature survey revealed that there is
only one report involving a three-component condensation between aldehydes,
(phenylsulfonyl)acetonitrile, and a-naphthol [29]. Indeed, to the best of our
knowledge, there are no reports on the diversity-oriented, catalyst-free synthesis of a
library of this type of biologically active compound. In continuation of our research
on multi-component reactions [30, 31], a simple, new, and efficient protocol for the
preparation of 4-(aryl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine deriva-
tives in glycerol media is described for the first time (Scheme 1).
Experimental
General
All reagents were purchased from Merck or Aldrich companies and were used
without further purification. All yields refer to separated products after purification.
The FT-IR spectra were recorded on a FT-IR spectroscopy Perkin Elmer BX-II. 1H
Scheme 1 Synthesis of 4-(aryl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine derivatives via three-
component reaction of aromatic aldehydes, (phenylsulfonyl)acetonitrile, and a-naphthol in glycerol
media under thermal conditions
123

A. Morshedi, H. R. Shaterian
NMR and 13C NMR spectra were recorded on Bruker 300 MHz spectrometer in
DMSO-d6 with TMS as an internal standard. Mass spectra were recorded using
Agilent Technologies Model: 5975C VL MSD with Tripe-Axis Detector; EI mode
at 70 eV. The spectral and analytical data for the selected compounds are presented
below. Melting points were determined in open capillaries using a BUCHI510
melting point apparatus. Thin-layer chromatography (TLC) was performed on
silica-gel Poly Gram SIL G/UV 254 plates.
General procedure for the asymmetric synthesis of 4-(aryl)-3-(phenylsulfonyl)-
4H-benzo[h]chromen-2-amine derivatives
(Phenylsulfonyl)acetonitrile (1 mmol) was added to a round-bottom flask containing
glycerol (5 mL) and benzaldehyde (1 mmol). The mixture was stirred at 80 °C.
After formation of the cyano-olefin (verified with TLC), a-naphthol (1 mmol) was
added to the reaction mixture, and it was allowed to stir until completion (TLC).
Then, for the work-up procedure, warm water was added to the reaction mixture,
glycerol dissolved and the insoluble solid crude product was separated by simple
filtration. The desired solid product was washed by warm water. Experimental
observation showed us that pure isolated product was obtained. The filtrate
containing glycerol was extracted with methyl t-butyl ether (3 9 10 mL) to remove
any organic compounds dissolved in the aqueous phase. The aqueous layer was
separated and the water was evaporated under reduced pressure to give pure
glycerol which was used for the next run under similar reaction conditions.
4-(4-chlorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4i)
Solid, yield: 92%, m.p. 223–225 °C; IR (KBr) (m, cm-1): 3466, 3340, 3060, 1652,
1
1625, 1261, 1185; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.10 (d, J = 12 Hz,
1H), 7.86 (dd, J = 9 & 6 Hz, 2H), 7.80–7.68 (m, 2H), 7.61–7.20 (m, 9H), 7.09 (t,
J = 9 Hz, 2H), 6.99 (t, J = 9 Hz, 1H), 5.45 (s, 1H); 13C NMR (76 MHz, DMSO) (d,
ppm): 158.71, 158.67, 145.26, 144.15, 143.05, 133.03, 132.65, 131.42, 129.52,
129.28, 128.69, 128.10, 127.19, 127.15, 126.22, 126.17, 124.66, 123.16, 121.28,
121.11, 82.70; MS (EI): m/z 447.1.
4-(2,6-dichlorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4j)
Solid, yield: 93%, m.p. 229–231 °C; IR (KBr) (m, cm-1): 3448, 3325, 1654, 1625,
1263, 1196; 1H NMR (300 MHz, DMSO-d6) (d, ppm): 8.31 (d, J = 9 Hz, 1H), 7.84
(d, J = 9 Hz, 1H), 7.68–7.58 (m, 5H), 7.58–7.45 (m, 4H), 7.37 (t, J = 6 Hz, 2H),
7.14 (t, J = 9 Hz, 1H), 7.03–6.88 (m, 2H), 6.11 (s, 1H); 13C NMR (76 MHz,
DMSO) (d, ppm): 158.83, 143.65, 143.46, 137.77, 135.64, 135.47, 133.32, 132.61,
130.60, 129.64, 129.12, 128.98, 128.09, 127.42, 127.24, 125.81, 124.90, 124.52,
122.61, 121.40, 115.79, 78.59, 36.82; MS (EI): m/z 481.1.
123

Green approach to synthesis of novel and broad…
4-(2-chlorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4k)
Solid, yield: 92%, m.p. 206–208 °C; IR (KBr) (m, cm-1): 3466, 3348, 3059, 1653,
1
1627, 1262, 1199; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.33 (d, J = 9 Hz,
1H), 7.85 (d, J = 6 Hz, 1H), 7.71 (d, J = 6 Hz, 2H), 7.66–7.47 (m, 6H), 7.39 (t,
J = 6 Hz, 2H), 7.27–7.17 (m, 3H), 7.10–7.06 (m, 2H), 5.55 (s, 1H); 13C NMR
(76 MHz, DMSO) (d, ppm): 158.70, 143.73, 142.96, 142.88, 133.14, 132.69,
131.71, 130.87, 129.83, 129.24, 128.62, 128.09, 128.02, 127.30, 127.23, 126.07,
125.26, 124.76, 123.10, 121.36, 119.78, 81.73, 38.19; MS (EI): m/z 447.1.
3-(phenylsulfonyl)-4-(o-tolyl)-4H-benzo[h]chromen-2-amine (4l)
Solid, yield: 90%, m.p. 219–221 °C; IR (KBr) (m, cm-1): 3462, 3335, 3066, 1654,
1
1625, 1261, 1189; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.32 (d, J = 9 Hz,
1H), 7.86 (d, J = 9 Hz, 1H), 7.66–7.44 (m, 8H), 7.33 (t, J = 9 Hz, 2H), 7.12 (d,
J = 9 Hz, 1H), 7.01–6.85 (m, 4H), 5.33 (s, 1H), 2.46 (s, 3H); 13C NMR (76 MHz,
DMSO) (d, ppm): 158.27, 158.22, 144.28, 144.01, 142.74, 134.81, 132.97, 132.47,
130.73, 129.51, 129.06, 128.07, 127.13, 126.77, 126.69, 126.09, 125.93, 124.56,
123.10, 121.30, 121.08, 83.10, 37.72, 19.67; MS (EI): m/z 427.2.
4-(2-fluorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4m)
Solid, yield: 91%, m.p. 209–211 °C; IR (KBr) (m, cm-1): 3446, 3317, 1653, 1627,
1262, 1188; 1H NMR (300 MHz, DMSO-d6) (d, ppm): 8.32 (d, J = 9 Hz, 1H), 7.85
(d, J = 9.0 Hz, 1H), 7.72 (d, J = 9.0 Hz, 2H), 7.65–7.47 (m, 6H), 7.39 (t,
J = 9.0 Hz, 2H), 7.27–7.20 (m, 2H), 7.16–7.08 (m, 1H), 7.01–6.90 (m, 2H), 5.29 (s,
1H); 13C NMR (76 MHz, DMSO) (d, ppm): d 161.54, 158.89, 158.30, 143.95,
143.23, 133.10, 132.67, 132.55, 132.38, 130.30, 130.25, 129.27, 129.09, 128.98,
128.10, 127.25, 127.18, 126.04, 125.87, 124.88, 124.69, 123.07, 121.30, 119.64,
115.95, 115.66, 81.04, 35.72; MS (EI): m/z 431.2.
4-(3-chlorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4n)
Solid, yield: 91%, m.p. 267–269 °C; IR (KBr) (m, cm-1): 3429, 3325, 3062, 1650,
1
1622, 1262, 1190; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.30 (d, J = 9.0 Hz,
1H), 7.87 (d, J = 9.0 Hz, 1H), 7.77–7.74 (m, 2H), 7.65–7.49 (m, 6H), 7.45–7.38 (m,
3H), 7.23–7.11 (m, 4H), 5.11 (s, 1H); 13C NMR (76 MHz, DMSO) (d, ppm):
158.82, 148.54, 144.07, 143.10, 133.40, 133.07, 132.76, 130.73, 129.27, 128.11,
127.42, 127.24, 127.18, 126.80, 126.37, 126.18, 126.13, 124.72, 123.14, 121.30,
120.95, 82.40, 41.05; MS (EI): m/z 447.2.
3-(phenylsulfonyl)-4-(p-tolyl)-4H-benzo[h]chromen-2-amine (4o)
Solid; yield: 90%, m.p. 267–269 °C; IR (KBr) (m, cm-1): 3457, 3338, 3019, 2917,
1652, 1625, 1260, 1184; 1H NMR (300 MHz, DMSO-d6) (d, ppm): 8.30 (d,
J = 9.0 Hz, 1H), 7.85 (d, J = 9.0 Hz, 1H), 7.73 (d, J = 6.0 Hz, 2H), 7.47 (m, 9H),
123

A. Morshedi, H. R. Shaterian
7.10 (d, J = 9.0 Hz, 2H), 6.94 (d, J = 6.0 Hz, 2H), 5.01 (s, 1H), 2.18 (s, 3H); 13C
NMR (76 MHz, DMSO) (d, ppm): 158.65, 144.25, 143.35, 142.99, 135.83, 132.92,
132.51, 129.29, 129.20, 128.08, 127.56, 127.05, 127.03, 126.38, 126.17, 124.49,
123.17, 121.87, 121.24, 83.20, 41.18, 20.98; MS (EI): m/z 427.2.
4-(4-nitrophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4p)
Solid, yield: 95%, m.p. 208–210 °C; IR (KBr) (m, cm-1): 3463, 3337, 3071, 1652,
1
1627, 1263, 1186; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.33 (d, J = 9.0 Hz,
1H), 8.01 (d, J = 9.0 Hz, 2H), 7.86 (d, J = 6.0 Hz, 1H), 7.78 (d, J = 9.0 Hz, 2H),
7.69–7.44 (m, 8H), 7.47–7.31 (m, 3H), 5.26 (s, 1H); 13C NMR (76 MHz, DMSO)
(d, ppm): 158.76, 153.85, 146.42, 144.01, 143.17, 133.19, 132.79, 129.36, 129.01,
128.13, 127.39, 127.26, 126.18, 126.10, 124.81, 124.10, 123.14, 121.35, 120.10,
82.14, 41.18; MS (EI): m/z 458.2.
Results and discussion
At first, to optimize reaction conditions for the synthesis of 4-(aryl)-3-(phenylsul-
fonyl)-4H-benzo[h]chromen-2-amine, the pilot reaction was subjected using
(phenylsulfonyl)acetonitrile, a-naphthol and benzaldehyde (reaction model). In a
model reaction, a mixture of (phenylsulfonyl)acetonitrile (1 mmol), a-naphthol
(1 mmol) and benzaldehyde (1 mmol) was stirred in different amounts of glycerol
Table 1 Optimizing of glycerol amounts in the synthesis of 4-phenyl-3-(phenylsulfonyl)-4H-benzo[h]-
chromen-2-amine 4aa
Entry
Glycerol (mL)
Time (min)
Yield (%)b
1
2
3
4
5
3
4
5
6
7
140
110
90
86
86
88
88
88
90
100
aThe reaction was carried out with 1 (1 mmol), 2 (1 mmol), 3 (1 mmol) in different amounts of glycerol
at 80 °C
bIsolated yields
123

Green approach to synthesis of novel and broad…
Table 2 Synthesis of 4aa in different temperatures
Entry
Temperature (°C)
Time (h)
Yield (%)b
1
2
3
4
r.t.
60
6
70
74
88
88
2
80
1.5
1.5
100
aThe reaction was carried out with 1 (1 mmol), 2 (1 mmol), 3 (1 mmol) and glycerol (5 mL)
bIsolated yields
and also at various temperatures (Tables 1, 2). To find the best efficiency, we
carried out this reaction in different common solvents such as acetonitrile, DMF,
toluene, DMSO, and neat conditions at 80 °C; no product was observed (Table 3,
entries 1, 2, 3, 4 and 7). Only a trace amount of products was detected in ethanol and
water (Table 3, entries 5 and 6). In summary, the best results were obtained in
glycerin (5 mL) at 80 °C in 1.5 h, and glycerol shows higher reactivity than other
solvents because of multiple hydrogen bonds.
With these results in hand, three-component condensation of substituted aromatic
aldehydes, (phenylsulfonyl)acetonitrile, and a-naphthol was investigated under the
optimized reaction conditions for preparation of 4-(aryl)-3-(phenylsulfonyl)-4H-
benzo[h]chromen-2-amines (Table 4). The substrate scope of the reaction was then
evaluated using a variety of structurally diverse aldehydes. The presence of
electron-withdrawing groups relate to electron-donating groups afforded the
corresponding products in shorter reaction times with higher yield (Table 4).
The mechanism proposed for preparation of 4-(aryl)-3-(phenylsulfonyl)-4H-
benzo[h]chromen-2-amine from benzaldehyde, (phenylsulfonyl)acetonitrile, and a-
naphthol in the presence of glycerol is depicted in Scheme 2. According to the
literature [32, 33], glycerol activated staring materials and intermediates by
hydrogen bonding characters. Benzylidene (phenylsulfonyl)acetonitrile, containing
Table 3 The study of effects of different solvents in the synthesis of 4aa
Entry
Solvent (5 mL)
Temperature (°C)
Time (h)
Yield (%)b
1
2
3
4
5
6
7
Acetonitrile
DMF
80
80
80
80
80
80
80
12
12
12
12
12
12
12
No reaction
No reaction
No reaction
No reaction
Trace
Toluene
DMSO
Ethanol
Water
Trace
Neat
No reaction
aThe reaction was carried out with 1 (1 mmol), 2 (1 mmol), 3 (1 mmol)
bIsolated yields
123

A. Morshedi, H. R. Shaterian
Table 4 Scope and generality of the synthesis of the 4-(aryl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-
amine derivatives 4a–p
No. Aldehyde
Products
Time (min)
90
Yield (%)a m.p (°C)
m.p (°C) [Refs.]
248–251 [23–25]
4a
88
249–250
4b
120
85
221–223
222–225 [23–25]
4c
80
91
252–254
251–254 [23–25]
4d
4e
100
89
93
256–258
252–254
258–261 [23–25]
254–257 [23–25]
80
4f
80
92
278–280
276–278 [23–25]
4g
130
89
224–225
225–227 [23–25]
4h
110
90
156–159
156–158 [23–25]
123

Green approach to synthesis of novel and broad…
Table 4 continued
No. Aldehyde
Products
Time (min)
Yield (%)a m.p (°C)
92 223–225
m.p (°C) [Refs.]
4i
80
New compound in
this work
4j
70
93
229–231
New compound in
this work
4k
80
90
92
90
206–208
219–221
New compound in
this work
4l
New compound in
this work
4m
70
80
91
91
209–211
267–269
New compound in
this work
4n
New compound in
this work
4o
90
90
199–201
New compound in
this work
4p
60
95
208–210
New compound in
this work
aYields refer to isolated pure products. Base on the reaction of substituted benzaldehyde (1 mmol),
(phenylsulfonyl)acetonitrile (1 mmol), and a-naphthol (1 mmol) in glycerol media at 80 °C
123

A. Morshedi, H. R. Shaterian
Scheme 2 Plausible mechanism for preparation of 4-(aryl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-
amine
an electron-poor C=C double bond, is formed quantitatively by Knoevenagel
addition of (phenylsulfonyl)acetonitrile to the aromatic aldehyde in glycerol media.
C-alkylation of a-naphthol occurs by the nucleophilic attack on electron-poor C=C
double and gave intermediate (I), which is then cyclized by intramolecular
nucleophilic attack of an OH group on the cyano (CN) moiety to give intermediate
(II). Subsequent tautomerization produced the 4-(aryl)-3-(phenylsulfonyl)-4H-
benzo[h]chromen-2-amine.
We also investigated recycling of the glycerol. Glycerol was dissolved in warm
water while the product remained insoluble in water. The solid product was
separated by simple filtration. The filtrate containing glycerol was extracted with
Fig. 1 Recyclability of glycerol
123

Green approach to synthesis of novel and broad…
methyl t-butyl ether (3 9 10 mL) to remove any organic compounds dissolved in
the aqueous phase. The aqueous layer was separated and the water was evaporated
under reduced pressure to give pure glycerol, which was used for the next run under
similar reaction conditions. The recovered glycerol was reused for five runs without
significant loss of activity. The findings of this study are shown in Fig. 1.
Conclusions
In summary, an efficient protocol for the one-pot preparation of 4-(aryl)-3-
(phenylsulfonyl)-4H-benzo[h]chromen-2-amine derivatives via three-component
reaction of aromatic aldehydes, (phenylsulfonyl)acetonitrile, and a-naphthol in
glycerol media as a commercially available, environmental friendly and reusable
compound was described. The reactions were carried out under thermal conditions
with short reaction times and produced the corresponding products in good to
excellent yields. Also, glycerol could be successfully recovered and recycled for at
least five runs without significant loss of activity. The one-pot nature and the use of
glycerol as an environmentally and eco-friendly material make it an interesting
alternative towards diversity-oriented synthesis of novel 4-(aryl)-3-(phenylsul-
fonyl)-4H-benzo[h]chromen-2-amine derivatives.
Acknowledgements We gratefully appreciate the University of Sistan and Baluchestan Research
Councils for the financial support of this work.
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