I2-Catalyzed transformation of: O -aminobenzamide to o -ureidobenzonitrile using isothiocyanates

Article abstract of DOI:10.1039/d0ob00118j

The present work describes an unexpected and unique protocol for the iodine catalysed synthesis of o-ureidobenzonitriles using o-aminobenzamides and isothiocyanates via intramolecular rearrangement. The metal-free route achieved here is insensitive to moisture and applicable to the synthesis of a wide variety of o-ureidobenzonitriles with excellent yields even in a scalable fashion.

Full text of DOI:10.1039/d0ob00118j

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Chem., 2020, DOI: 10.1039/D0OB00118J.
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DOI: 10.1039/D0OB00118J
ARTICLE
I2 – Catalyzed Transformation of o-Aminobenzamide to o-
Ureidobenzonitrile Using Isothiocyanates
Received 00th January 20xx,
Accepted 00th January 20xx
Sadashivamurthy Shamanth,a Nagaraju Chaithra,a Mahesha Gurukiran,a Mahesha Mamatha,b N. K.
Lokanath,c and Kanchugarakoppal S Rangappa*a and Kempegowda Mantelingu*a
DOI: 10.1039/x0xx00000x
Present work describes the unexpected and unique protocol for the iodine catalysed synthesis of o-ureidobenzonitriles
using o-aminobenzamides and isothiocyanates via intramolecular rearrangement. The metal free route achieved here is
insensitive to moisture and applicable to the synthesis of wide variety of o-ureidobenzonitriles with excellent yields even
in scalable fashion.
Introduction
Nitriles, which have extensive applications in organic synthesis
and pharmaceuticals are generally synthesized by the
Urea and its derivatives have significant role in drug discovery
and medicinal chemistry due to their ability to form stable
hydrogen bonds with protein and receptor targets.1 Urea
functionality is incorporating in drug design to enhance the
selectivity and potency of the drugs. Some of the urea
derivatives are in use as hypnotics, sedatives, anticonvulsants,
antibacterial, antiviral, anti-HIV and anticancer agents.2,3 The
FDA approved drugs Sorafenib, Linifanib and Lenvatinib which
contain diphenyl urea as a key moiety are being used in the
treatment of carcinoma and thyroid cancer (Fig. 1).4,5,6
dehydration of primary amides and aldoximes. The functional
group transformation of amide to nitrile is not an easy task,
which requires harsh, acidic dehydrating reagents such as
P2O5, POCl3, TiCl4 or SOCl2.7 Stephan Enthaler et al developed
the Cu and Zn catalyzed dehydration of amides to nitriles using
N-methyl-N-(trimethylsilyl)trifluoroacetamides as dehydrating
agent.8 Again, only few methods have been reported for the
synthesis of o-ureidobenzonitriles (Scheme 1). The traditional
method involves the reaction between o-aminobenzonitrile
and isocyanates in presence of base.9a The method reported
by Pedro Molina et al requires three steps, starting with o-
aminobenzamide (1a).9b
O
CF3
O
Cl
N
H
O
In continuation of our work on the synthesis of heterocyclic
compounds via novel methodologies,10 we initiated to
synthesize biologically active quinazolinone11 derivatives but
unexpectedly ended up with o-ureidobenzonitriles. Likewise,
recently we have reported an unprecedented procedure for
the synthesis of N, N’- substituted ureas.12
N
N
H
N
H
Sorafenib
H2N
H3CO
O
O
HN
N
N
H
N
NH2
H
O
Cl
F
O
Linifanib
3 step synthesis
Previous Work
(Pedro Molina et al)
H2N
N
Less substrate scope
N
H
N
H
H2N
O
Lenvatinib
O
CN
H
C
C
H
N
2. Ph3P
N
NH
2 1. NaN3
N3
C
O
R
Figure 1: Bioactive molecules containing urea moiety
3. R-NCO
Present Work
One step synthesis
H2N
O
CN
C
a. DOS in Chemistry, Manasagangotri, University of Mysore, Mysuru-570006,
Karnataka, India. E-mail: kmlingu@gmail.com, rangappaks@gmail.com
b. SRSMNGFG College, Barkur-576210, Udupi Dist., Karnataka, India.
H
N
H
N
S
I2, DMF
NH2
C
R2
C
c. DOS in Physics, Manasagangotri, University of Mysore, Mysuru-570006.
Electronic Supplementary Information (ESI) available: General experimental
protocols, characterization details, 1H-NMR, 13C-NMR, HRMS spectra of compounds
and Crystallographic data [CCDC Number-1974299]. See DOI: 10.1039/x0xx00000x
O
N
rt, 3 h
R2
R1
3
R1
1
2
o-ureidobenzonitrile
Scheme 1: Methods for the synthesis of o-ureidobenzonitriles
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ARTICLE
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After the confirmation of structure, we attempted to optimize
DOI: 10.1039/D0OB00118J
the reaction conditions to obtain the compound 3a in better
The most commonly used protocols for the synthesis of nitriles
and o-ureidobenzonitriles are expensive, moisture sensitive,
time consuming, requires high temperature and large amount
of activating reagents, have toxicological issues, narrow
substrate scope and mainly suffer from lower yield. Our
method is able to synthesize variety of o-ureidobenzonitriles
which includes phenyl, benzyl and aliphatic isothiocyanates, at
optimum conditions with maximum yields. Moreover, the
procured o-ureidobenzonitrile which contain nitrile group at
ortho position to urea is a precursor for the synthesis of
heterocycles like quinazolines and quinazolinones.9a,13
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yield (Table 1). In the beginning, o-aminobenzamide (1a) (1 eq)
and phenyl isothiocyanate (2a) (1 eq) were allowed to stir for
24 h in DMF (10 vol) solvent without I2, but no desired product
was observed (Table 1, entry 1). Then we tested with 0.6 and
0.7 eq of I2 and obtained slightly lower yields compared to the
yield obtained with 0.5 eq of I2 (Table 1, entries 2-4). After
that, we tried with 0.4, 0.3 and 0.2 eq of I2 and procured 80, 81
and 50 % yield respectively (Table 1, entries 5-7). With these
results, 0.3 eq of I2 was found to be enough for better yield
(Table 1, entry 6). Extending the reaction time with 0.3 eq of I2
didn’t improve the yield (Table 1, entry 8). In addition, we
investigated the temperature dependency of the reaction by
Results and Discussion
Initially we started the work with o-aminobenzamide (1a),
phenyl isothiocyanate (2a) using 0.5 eq of I2 as catalyst in DMF
solvent and stirred the contents for 6 hr at room temperature.
A new spot observed in TLC was isolated with 80 % yield. The
molecular ion peak (m/z = 238.0685) observed in the mass
spectra supported the formation of expected product 2-
(phenylamino)quinazolin-4(3H)-one (Scheme 2). However, the
ambiguity raised when we observed two –NH- protons in the
o
o
o
keeping it at 40 C, 50 C and 60 C but recorded lesser yields
compared to room temperature condition (Table 1, entries 9-
11). Effect of solvent in terms of yield was also screened (Table
1, entries 12-19). From the Table 1, the best optimized
conditions for the reaction are: o-aminobenzamide (1a) (1
mmol), phenyl isothiocyanate (2a) (1 mmol) and I2 (0.3 mmol)
in DMF (1 ml) solvent stirred for 3 h at room temperature to
synthesize 1-(2-cyanophenyl)-3-phenylurea (3a) (Table 1, entry
6).
1
same region (9.402 & 8.747 ppm) of H-NMR spectra. Further
investigation of the product with 13C-NMR and crystal analysis
(Fig. 2) revealed the exact structure of the molecule, which is
nothing but 1-(2-cyanophenyl)-3-phenylurea (3a). Surprisingly,
the expected and obtained product’s molecular masses are
same.
Table 1: Optimization of the reaction conditions (catalyst
equivalence, solvent, temp., time) for the synthesis of 1-(2-
cyanophenyl)-3-phenylurea(3a).a
S
H2N
O
CN
C
O
C
N
H
N
H
N
NH2
I2, solvent
C
C
O
NH
S
temp., time
C
H2N
O
C
N
N
N
H
C
1a
2a
3a
NH2
Expected Product
N
C
2a
Entry
I2
Solvent
Temp.
oC
rt
Time
h
24
%
Yieldb
--
H
N
H
N
1a
(equivalence)
I2, DMF, rt
C
1
2
0.0
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMSO
EtOAc
EtOH
O
0.5
0.6
0.7
0.4
0.3
0.2
0.3
0.3
0.3
0.3
0.3
0.3
0.3
rt
rt
3
3
80
78
76
80
81
50
80
75
71
69
78
50
65
3a
Obtained Product
3
Scheme 2: Expected and obtained product.
4
rt
3
5
rt
3
6
rt
3
7
rt
3
8
rt
15
3
9
40
50
60
rt
10
11
12
13
14
3
3
3
rt
3
Figure 2: Single crystal structure of 1-(2-cyanophenyl)-3-
phenylurea (3a): CCDC Number-1974299.
rt
3
2 | J. Name., 2012, 00, 1-3
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Journal Name
ARTICLE
performed at ordinary conditions. Also, we stirred 1,3-
DOI: 10.1039/D0OB00118J
diphenylthiourea in open air in presence of iodine and DMF
solvent for 24 h, the thiourea remained as it is without getting
oxidized to urea. From literature also it is evident that,
thioureas are stable and their oxidation to urea require specific
conditions.14
15
16
17
18
19
0.3
0.3
0.3
0.3
0.3
CHCl3
Toulene
CH3CN
DCM
rt
rt
rt
rt
rt
3
3
3
3
3
--
--
View Article Online
63
--
H2O
--
aReaction conditions: Reactions were performed with 1a (1 mmol)
and 2a (1 mmol) using I2 (0.3 mmol) in DMF solvent (1 ml) at rt for 3
h. b Isolated yield.
N
H2N
O
C
C
S
C
N
H
N
H
N
I2, DMF
rt. 3 h
NH3
C
O
R2
R2
With the help of above optimized reaction conditions, we
further explored the scope and generality of the reaction using
various substituted o-aminobenzamides 1 and isothiocyanates
2 and the results are summarized in Scheme 3. Both electron
donating and withdrawing groups at different positions on
phenyl ring of isothiocyantes gave almost similar yields with o-
aminobenzamides. The yields obtained with benzyl and alkyl
isothiocyanates are also comparable with phenyl
isothiocyanates. These examples clearly describe the utility of
the protocol for wider applicability. The approach of this
reaction is also good even in gram scale synthesis. We
synthesized 1a in 2.0 g scale and procured 78 % yield which
was 81 % when synthesized in mmol scale. We tried to extend
the scope of the reaction by taking o-(methylamino)benzamide
and o-hydroxybenzamide in place of o-aminobenzamide, but
the starting materials were remained as it is without
undergoing any further reactions (Scheme 4).
R1
R1
1
3
2
3a, Y=H, 81%
CN
3b, Y=OCH3, 83%
3c, Y=CH3, 80%
3d, Y=Cl, 82%
3e, Y=F, 78%
H
H
N
N
C
O
Y
3f, Y=CF3, 81%
3g, Y=NO2, 80%
CN
H
N
H
N
3h, Y=OCH3, 80%
3i, Y=CH3, 85%
3j, Y=Br, 82%
Y
C
O
3k, Y=Cl, 84%
CN
3l, R1=Cl, Y=H, 80%
H
N
H
N
3m, R1=Cl, Y=CH3, 78%
3n, R1=Cl, Y=F, 78%
3o, R1=F, Y=H, 78%
3p, R1=F, Y=F, 76%
C
A
possible reaction mechanism for the formation of o-
O
ureidobenzonitrile has been proposed (Scheme 5). The reaction
of o-aminobenzamide 1a with phenyl isothiocyante 2a first
produces the thiourea intermediate A. The Lewis acid-base
interaction between molecular iodine and sulfur atom of
thiocarbonyl group, followed by the nucleophilic attack of
carbonyl oxygen on the thiocarbonyl carbon leads to the
formation of cyclized thiol intermediate B with the regeneration
of iodine. This is the key step which resulted the unexpected
chemistry. This unstable intermediate B further undergoes
intramolecular rearrangement to produce o-ureidobenzonitrile
3a with the liberation of H2S. At the end of the reaction, the
amide group of o-aminobenzamide 1a transformed to nitrile and
amine group converted to urea.
R1
Y
Y
CN
H
N
H
N
3q,R1=Cl, Y=Br, 80%
3r, R1=F, Y=Br, 77%
3s, R1=F, Y=Cl, 81%
C
O
R1
CN
Cl
H
N
H
N
3t, 75%
C
O
Cl
CN
3u, R1=H, 75%
3v, R1=F, 76%
H
N
H
N
In order to support the proposed mechanism, we performed a
few reactions (Scheme 6). Suppose the dehydration of amide
to nitrile and the conversion of thiocarbonyl to carbonyl are
two independent reactions, then the reactions (a), (b) and (c)
have to be ended with positive results as shown in Scheme 6,
but they didn’t. Only the corresponding thiourea
intermediates have formed without affecting the amide
moiety. The yields of thiourea intermediates formed were
around 75%. The reaction (d) was performed under nitrogen
atmosphere and obtained the product 3a with almost same
yield compared to the yield obtained when the reaction was
C
O
R1
CN
H
N
H
N
3w, R1=H, 76%
3x, R1=F, 77%
C
O
R1
Scheme 3: Substrate scope for the synthesis of o-
ureidobenzonitrile.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
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ARTICLE
Journal Name
S
C
N
On the basis of the experimental results of Scheme 6 and
literature reports,9b,15 we can conclude that the product is
forming through intramolecular rearrangement mechanism
and the oxygen atom which is re[placing sulfur is from amide
moiety only as depicted in Scheme 5.
H2N
O
View Article Online
CN
C
DOI: 10.1039/D0OB00118J
H
H
N
N
NH2
I2, DMF
N2 atm
C
O
(d)
2a
1a
3a
H
H
H
H
N
I2, DMF
S
H2N
O
N
N
N
CN
C
C
S
C
O
C
N
H
N
H
N
(e)
rt, 24 h
N
I2, DMF
rt, 12 h
C
O
open air
(a)
Scheme 6: Supporting reactions for the proposed mechanism.
S
C
N
H2N
O
CN
C
Experimental
H
N
O
OH
I2, DMF
rt, 12 h
C
O
(b)
Materials and methods
All the reagents, chemicals and solvents used were from Sigma
Aldrich and Sd-fine chemicals and were used without
additional purification. The instrumental techniques employed
for the characterization of the newly synthesized compounds
Scheme 4: Extended reactions
include H and 13C NMR and HRMS. H and 13C NMR spectra
were recorded on Agilent 400 MHz spectrometer in DMSO-d6
solution using tetramethylsilane (TMS) as internal standard.
Chemical shifts were recorded in ppm relative to TMS. High
resolution mass spectra were obtained via electrospray (ESI).
Column chromatography was performed on silica gel 60 (60–
120 mesh) and thin layer chromatography was performed on
TLC plates (Merck, silica gel 60 F254). The mobile phases
employed for column chromatography and TLC were hexane
and ethyl acetate in 9:1 ratio.
1
1
S
H2N
O
I
C
N
I
NH
NH2
H2N
O
I2
C
S
NH
2a
1a
A
-I2
.
NH
Synthetic procedures
N
O
CN
S
C
H
C
H
N
H
N
H
-H2S
NH
General procedure for synthesis of o-ureidobenzonitriles (3a-
3x)
C
O
The mixture of o-aminobenzamide (1) (1 mmol) and
isothiocyanates (2) (1 mmol) were allowed to stir in DMF
solvent (2 ml) in presence of molecular iodine (0.3 mmol) at
room temperature for 3 h. After that, the contents were
poured to 30 ml, 10 % aqueous solution of sodium thiosulfate
and extracted with 30 ml ethyl acetate. The ethyl acetate
extract was separated and dried over anhydrous sodium
sulfate then the solvent was removed under reduced pressure
to afford corresponding o-ureidobenzonitrile. The crude
residue thus obtained was purified by column chromatography
over silica gel using ethyl acetate in hexane as eluent to get
pure o-ureidobenzonitrile.
3a
B
Scheme 5: Proposed mechanism for the synthesis of o-
ureidobenzonitrile.
H2N
O
NCS
H
N
H
N
NC
I2, DMF
rt, 3 h
C
O
(a)
NH2
H2N
O
NCS
H
N
H
N
I2, DMF
rt, 3 h
C
O
1-(2-cyanophenyl)-3-phenylurea (3a)
Yield: 192 mg, 81 %; MP. 178 °C; White solid; H-NMR (400
(b)
1
NC
CN
MHz, DMSO-d6): δ ppm : 6.971-7.008 (t, 1H, Ar, J=7.6 Hz),
7.139-7.176 (t, 1H, Ar, J=7.6 Hz), 7.269-7.307 (t, 2H, Ar, J=8 Hz),
7.450-7.470 (d, 2H, Ar, J=8 Hz), 7.602-7.641 (t, 1H, Ar, J=7.6
Hz), 7.718-7.738 (d, 1H, Ar, J=8 Hz), 8.059-8.080 (d, 1H, Ar,
J=8.4 Hz), 8.747 (s, 1H, -NH-), 9.402 (s, 1H, -NH-); 13C- NMR
(400 MHz, DMSO-d6): δ ppm: 102.452, 117.395, 118.826,
121.725, 122.795, 123.447, 129.343, 133.565, 134.421,
139.665, 142.389, 152.459; HRMS: m/z calculated for
[C14H11N3O+H+] = 238.0975: found = 238.0974.
NH2
H2N
O
NCS
NH2
H
N
H
N
I2, DMF
rt, 3 h
C
O
(C)
4 | J. Name., 2012, 00, 1-3
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146.252, 152.206; HRMS: m/z calculated for [C14H10N4O3+H+] =
1-(2-cyanophenyl)-3-(4-methoxyphenyl)urea (3b)
Yield: 222 mg, 83 %; MP. 188 °C; White solid; H-NMR (400 281.0826: found = 281.0830.
MHz, DMSO-d6): δ ppm : 3.687 (s, 3H, -OCH3,), 6.846- 6.868 (d, 1-(2-cyanophenyl)-3-(3-methoxyphenyl)urea (3h)
View Article Online
1
DOI: 10.1039/D0OB00118J
1
2H, Ar, J=8.8 Hz), 7.103-7.141 (t, 1H, Ar, J=7.6 Hz), 7.332-7.354 Yield: 214 mg, 80 %; MP. 188 °C; White solid; H-NMR (400
(d, 2H, Ar, J=8.8 Hz), 7.572- 7.610 (t, 1H, Ar, J=7.6 Hz), 7.688- MHz, DMSO-d6): δ ppm: 3.718 (s, 3H, -OCH3,), 6.564- 6.583 (d,
7.707 (d, 1H, Ar, J=7.6 Hz), 8.047-8.068 (d, 1H, Ar, J=8.4 Hz), 1H, Ar, J=7.6 Hz), 6.936-6.955 (d, 1H, Ar, J=7.6 Hz), 7.163-7.206
8.617 (s, 1H, -NH-), 9.183 (s, 1H, -NH-); 13C- NMR (400 MHz, (t, 3H, Ar, J=8.8 Hz), 7.604- 7.643 (t, 1H, Ar, J=8.0 Hz), 7.722-
DMSO-d6): δ ppm : 55.626, 102.121, 114.535, 117.405, 7.740 (d, 1H, Ar, J=7.2 Hz), 8.055-8.076 (d, 1H, Ar, J=8.4 Hz),
120.606, 121.491, 123.194, 132.612, 133.507, 134.373, 8.702 (s, 1H, -NH-), 9.379 (s, 1H, -NH-); 13C- NMR (400 MHz,
142.594, 152.527, 155.251; HRMS: m/z calculated for DMSO-d6): δ ppm : 55.392, 102.384, 104.573, 108.270,
[C15H13N3O2+H+] = 268.1081: found = 268.1084.
111.091, 117.376, 121.686, 123.466, 130.121, 133.555,
134.431, 140.862, 142.331, 152.381, 160.164; HRMS: m/z
1-(2-cyanophenyl)-3-(p-tolyl)urea (3c)
Yield: 201 mg, 80 %; MP. 196 °C; White solid; 1H-NMR calculated for [C15H13N3O2+H+] = 268.1081: found = 268.1085.
(400MHz, DMSO-d6): δ ppm: 2.219 (s, 3H, -CH3), 7.067-7.088 1-(2-cyanophenyl)-3-(m-tolyl)urea (3i)
(d, 2H, Ar, J=8.4 Hz), 7.116-7.155 (t, 1H, Ar, J=7.6 Hz), 7.310- Yield: 214 mg, 85 %; MP. 189 °C; White solid; H-NMR (400
1
7.331 (d, 2H, Ar, J=8.4 Hz), 7.577-7.621 (m, 1H, Ar), 7.694- MHz, DMSO-d6): δ ppm : 2.287 (s, 3H, -CH3), 6.823-6.841 (d,
7.716 (m, 1H, Ar), 8.042-8.063 (d, 1H, Ar, J=8.4 Hz), 8.658 (s, 1H, Ar, J=7.2 Hz), 7.162-7.200 (t, 2H, Ar, J=7.6 Hz), 7.237-7.257
1H, -NH-), 9.260 (s, 1H, -NH-); 13C- NMR (400 MHz, DMSO-d6): (d, 1H, Ar, J=8.0 Hz), 7.316 (s, 1H, Ar), 7.638 (s, 1H, Ar), 7.738-
δ ppm: 102.257, 117.395, 118.903, 121.598, 123.311, 129.712, 7.757 (d, 1H, Ar, J=7.6 Hz), 8.080-8.101 (d, 1H, Ar, J=8.4 Hz),
131.678, 133.536, 134.392, 137.048, 142.477, 152.430; HRMS: 8.713 (s, 1H, -NH-), 9.316 (s, 1H, -NH-); 13C- NMR (400 MHz,
m/z calculated for [C15H13N3O+H+] = 252.1137: found = DMSO-d6): δ ppm : 21.651, 102.306, 116.024, 117.396,
252.1142.
119.361, 121.628, 123.379, 123.544, 129.168, 133.546,
134.402, 138.527, 139.568, 142.429, 152.411; HRMS: m/z
1-(4-chlorophenyl)-3-(2-cyanophenyl)urea (3d)
1
Yield: 223 mg, 82 %; MP. 198 °C; White solid; H-NMR (400 calculated for [C15H13N3O+H+] = 252.1137: found = 252.1142.
MHz, DMSO-d6): δ ppm : 7.137-7.174 (t, 1H, Ar, J=7.2 Hz), 1-(3-bromophenyl)-3-(2-cyanophenyl)urea (3j)
7.305-7.327 (d, 2H, Ar, J=8.8 Hz), 7.458-7.480 (d, 2H, Ar, J=8.8 Yield: 258 mg, 82 %; MP. 191 °C; White solid; H-NMR (400 MHz,
1
Hz), 7.587-7.629 (m, 1H, Ar), 7.704- 7.726 (m, 1H, Ar), 8.016- DMSO-d6): δ ppm : 7.158-7.295 (m, 4H, Ar), 7.605- 7.643 (t, 1H, Ar,
8.036 (d, 1H, Ar, J=8 Hz), 8.725 (s, 1H, -NH-), 9.470 (s, 1H, -NH- J=7.6 Hz), 7.724-7.743 (d, 1H, Ar, J=7.6 Hz), 7.839 (s, 1H, Ar), 7.994-
); 13C- NMR (400 MHz, DMSO-d6): δ ppm : 102.724, 117.337, 8.015 (d, 1H, Ar, J=8.4 Hz), 8.767 (s, 1H, -NH-), 9.519 (s, 1H, -NH-);
120.353, 121.861, 123.641, 126.356, 129.177, 133.555, 13C- NMR (400 MHz, DMSO-d6): δ ppm : 103.016, 117.328, 117.658,
134.421, 138.644, 142.166, 152.401; HRMS: m/z calculated for 121.083, 122.056, 122.221, 123.846, 125.344, 131.269, 133.585,
[C14H10ClN3O+H+] = 272.0591: found = 272.0595.
1-(2-cyanophenyl)-3-(4-fluorophenyl)urea (3e)
Yield: 200 mg, 78 %; MP. 205 °C; White solid; H-NMR (400 1-(3-chlorophenyl)-3-(2-cyanophenyl)urea (3k)
MHz, DMSO-d6): δ ppm : 7.105-7.180 (m, 3H, Ar), 7.445- 7.478 Yield: 228 mg, 84 %; MP. 186 °C; White solid; H-NMR (400
(m, 2H, Ar), 7.601-7.639 (t, 1H, Ar, J=7.6 Hz), 7.718-7.737 (d, MHz, DMSO-d6): δ ppm : 7.022-7.041 (d, 1H, Ar, J=7.6 Hz),
1H, Ar, J=7.6 Hz), 8.034-8.055 (d, 1H, Ar, J=8.4 Hz), 8.702 (s, 7.179-7.198 (d, 1H, Ar, J=7.6 Hz), 7.232-7.252 (d, 1H, Ar, J=8
1H, -NH-), 9.388 (s, 1H, -NH-); 13C- NMR (400 MHz, DMSO-d6): Hz), 7.281-7.301 (d, 1H, Ar, J=8 Hz), 7.694 (s, 1H, Ar), 7.724-
δ ppm : 102.57, 115.74, 115.96, 117.36, 120.59, 120.66, 7.744 (d, 1H, Ar, J=8 Hz), 7.996-8.018 (d, 1H, Ar, J=8.8 Hz),
121.77, 123.50, 133.54, 134.41, 135.96, 142.32, 152.53, 8.771 (s, 1H, -NH-), 9.531 (s, 1H, -NH-); 13C- NMR (400 MHz,
156.86, 159.24; HRMS: m/z calculated for [C14H10FN3O+H+] = DMSO-d6): δ ppm : 102.996, 117.240, 117.337, 118.174,
134.451, 141.339, 142.020, 152.401; HRMS: m/z calculated for
[C14H10BrN3O+H+] = 316:0080: found = 316.0085.
1
1
256.0881: found = 256.0886.
122.046, 122.426, 123.836, 130.968, 133.595, 133.702,
134.461, 141.203, 142.010, 152.411; HRMS: m/z calculated for
1-(2-cyanophenyl)-3-(4-(trifluoromethyl)phenyl)urea (3f)
Yield: 247 mg, 81 %; MP. 185 °C; White solid; H-NMR (400 [C14H10ClN3O+H+] = 272.0591: found = 272.0595.
1
MHz, DMSO-d6): δ ppm: 7.158-7.196 (t, 1H, Ar, J=7.6 Hz), 1-(4-chloro-2-cyanophenyl)-3-phenylurea (3l)
1
7.303-7.321 (d, 1H, Ar, J=7.2 Hz), 7.484-7.523 (t, 1H, Ar, J=8 Yield: 217 mg, 80 %; MP. 204 °C; White solid; H-NMR (400
Hz), 7.552-7.573 (d, 1H, Ar, J=8.4 Hz), 7.599-7.641 (m, 1H, Ar), MHz, DMSO-d6): δ ppm : 6.968-7.004 (t, 1H, Ar, J=7.2 Hz),
7.719-7.742 (t, 1H, Ar, J=8.4 Hz), 7.987-8.039 (t, 2H, Ar, J=12.4 7.257-7.297 (t, 2H, Ar, J=8.4 Hz), 7.423-7.442 (d, 1H, Ar, J=7.6
Hz), 8.807 (s, 1H, -NH-), 9.704 (s, 1H, -NH-); 13C- NMR (400 Hz), 7.660-7.690 (m, 1H, Ar), 7.897- 7.903 (d, 1H, Ar, J=2.4 Hz),
MHz, DMSO-d6): δ ppm: 103.094, 114.720, 117.308, 119.040, 8.085-8.108 (d, 1H, Ar, J=9.2 Hz), 8.798 (s, 1H, -NH-), 9.406 (s,
122.386, 123.885, 130.471, 133.555, 134.431, 140.541, 1H, -NH-); 13C-NMR (400 MHz, DMSO-d6): δ ppm : 103.726,
141.961, 152.556; HRMS: m/z calculated for [C15H10F3N3O+H+] 116.121, 118.903, 122.951, 123.126, 126.716, 129.343,
= 306.0854 : found = 306.0859.
1-(2-cyanophenyl)-3-(4-nitrophenyl)urea (3g)
Yield: 226 mg, 80 %; MP. >250 °C; White solid; H-NMR (400 1-(4-chloro-2-cyanophenyl)-3-(p-tolyl)urea (3m)
MHz-DMSO-d6): δ ppm: 7.200-7.238 (t, 1H, Ar, J=7.6 Hz), Yield: 222 mg, 78 %; MP. 195 °C; White solid; H-NMR (400
7.630-7.692 (m, 3H, Ar), 7.752-7.772 (d, 1H, Ar, J=8 Hz), 7.981- MHz, DMSO-d6): δ ppm : 2.220 (s, 3H, -CH3-), 7.070-7.091 (d,
8.002 (d, 1H, Ar, J=8.4 Hz), 8.176- 8.198 (d, 2H, Ar, J=8.8 Hz), 2H, Ar, J=8.4 Hz), 7.302-7.322 (d, 2H, Ar, J=8 Hz), 7.646-7.674
8.934 (s, 1H, -NH-), 10.016 (s, 1H, -NH-); 13C- NMR (400 MHz, (m, 1H, Ar), 7.873-7.879 (d, 1H, Ar, J=2.4 Hz), 8.081-8.104 (d,
DMSO-d6): δ ppm : 103.639, 117.220, 118.252, 122.464, 1H, Ar, J=9.2 Hz), 8.727 (s, 1H, -NH-), 9.283 (s, 1H, -NH-); 13C-
124.332, 125.607, 133.643, 134.643, 141.572, 141.913, NMR (400 MHz, DMSO-d6): δ ppm : 103.580, 116.131, 119.010,
123.048, 126.589, 129.722, 131.872, 132.563, 134.441,
132.602, 134.470, 139.461, 141.562, 152.274; HRMS: m/z
calculated for [C14H10ClN3O+H+] = 272.0591: found = 272.0593.
1
1
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J. Name., 2013, 00, 1-3 | 5
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Journal Name
136.863, 141.660, 152.264; HRMS: m/z calculated for DMSO-d6): δ ppm : 104.95, 105.05, 116.23, 117.67, 119.55,
View Article Online
[C15H12ClN3O+H+] = 286.0742: found = 286.0743.
119.81, 121.10, 121.82, 122.04, 122.18, 124.91, 124.99,
DOI: 10.1039/D0OB00118J
1-(4-chloro-2-cyanophenyl)-3-(4-fluorophenyl)urea (3n)
Yield: 225 mg, 78 %; MP. 196 °C; White solid; H-NMR (400 m/z calculated for [C14H9ClFN3O + H+] = 290.0496: found =
MHz, DMSO-d6): δ ppm : 7.094-7.139 (t, 2H, Ar, J=9.2 Hz), 290.0502.
125.32, 131.22, 138.76, 141.33, 152.55, 156.29, 158.71; HRMS:
1
7.425-7.460 (m, 2H, Ar), 7.659-7.688 (m, 1H, Ar), 7.890-7.896 1-(2-cyanophenyl)-3-(2,4-dichlorophenyl)urea (3t)
1
(d, 1H, Ar, J=2.4 Hz), 8.057-8.079 (d, 1H, Ar, J=8.8 Hz), 8.763 (s, Yield: 279 mg, 75 %; MP. 184 °C; White solid; H-NMR (400 MHz,
1H, -NH-), 9.405 (s, 1H, -NH-); 13C- NMR (400 MHz, DMSO-d6): DMSO-d6): δ ppm: 7.212 (s, 1H, Ar), 7.383-7.400 (d, 1H, Ar, J = 6.8
δ ppm : 103.862, 115.771, 115.995, 116.121, 120.674, Hz), 7.631 (s, 2H, Ar), 7.759 (s, 1H, Ar), 7.986-8.002 (d, 1H, Ar, J = 6.0
120.752, 123.184, 126.794, 132.602, 134.461, 135.784, Hz), 8.097-8.116 (d, 1H, Ar, J = 7.6 Hz), 9.039 (s, 1H, -NH-), 9.518 (s,
141.524, 152.372, 156.945, 159.319; HRMS: m/z calculated for 1H, -NH-); 13C- NMR (400 MHz, DMSO-d6): δ ppm:103.321, 117.554,
[C14H9ClFN3O+H+] = 290.0496: found = 290.0507.
122.798, 123.771, 124.112, 124.229, 127.498, 128.218, 129.278,
133.880, 134.561, 135.378, 141.926, 152.541; HRMS: m/z
1-(2-cyano-4-fluorophenyl)-3-phenylurea (3o)
1
Yield: 199 mg, 78 %; MP. 191 °C; White solid; H-NMR (400 calculated for [C14H9Cl2N3O + H+] = 306.0201: found = 306.0208.
MHz, DMSO-d6): δ ppm : 6.963-6.999 (t, 2H, ar, J=7.2 Hz),
1-benzyl-3-(2-cyanophenyl)urea (3u)
7.259-7.297 (t, 2H, Ar, J=7.6 Hz), 7.445-7.465 (d, 2H, Ar, J=8.0
Hz), 7.518-7.560 (m, 1H, Ar), 7.735- 7.755 (t, 1H, Ar, J=2.4 Hz),
7.944-7.979 (m, 1H, Ar), 8.932 (s, 1H, -NH-), 9.452 (s, 1H, -NH-)
1
Yield: 188 mg, 75 %; MP. 208 °C; White solid; H-NMR (400
MHz, DMSO-d6): δ ppm : 4.304-4.317 (d, 2H, -CH2-, J=5.6 Hz),
7.074-7.111 (t, 1H, Ar, J=7.2 Hz), 7.111-7.360 (m, 5H, Ar),
7.412-7.426 (d, 1H, Ar, J=5.6 Hz), 7.553- 7.590 (t, 1H, Ar, J=7.6
Hz), 7.666-7.683 (d, 1H, Ar, J=6.8 Hz), 8.055-8.077 (d, 1H, -NH-,
J=8.8 Hz), 8.569 (s, 1H, -NH-); 13C- NMR (400 MHz, DMSO-d6): δ
ppm : 43.286, 101.537, 117.464, 121.190, 122.717, 127.349,
127.728, 128.827, 133.429, 134.305, 140.084, 143.139,
154.979; HRMS: m/z calculated for [C15H13N3O+H+] = 252.1136:
found = 252.1139.
;
13C- NMR (400 MHz, DMSO-d6): δ ppm : 104.242, 104.339,
116.287, 118.874, 119.468, 119.731, 121.832, 122.056,
122.805, 124.478, 124.566, 129.314, 139.170, 139.637; HRMS:
m/z calculated for [C14H10FN3O+H+] = 256.0881: found=
256.0885.
1-(2-cyano-4-fluorophenyl)-3-(4-fluorophenyl)urea (3p)
1
Yield: 207 mg, 76 %; MP. 208 °C; White solid; H-NMR (400
MHz, DMSO-d6): δ ppm : 7.124-7.168 (t, 2H, Ar, J=8.8 Hz),
7.459-7.494 (m, 2H, Ar), 7.534-7.585 (m, 1H, Ar), 7.761-7.789
(m, 1H, Ar), 7.977-8.013 (m, 1H, Ar), 8.742 (s, 1H, -NH-), 9.345
(s, 1H, -NH-); 13C- NMR (400 MHz, DMSO-d6): δ ppm : 104.602,
104.699, 115.703, 115.917, 116.287, 119.458, 119.721,
120.538, 120.616, 121.774, 121.998, 124.683, 124.761,
136.017, 139.092, 139.072, 152.751, 156.127, 156.847,
158.531, 159.221; HRMS: m/z calculated for [C14H9F2N3O+H+] =
274.0786: found = 274.0786.
1-benzyl-3-(2-cyano-4-fluorophenyl)urea (3v)
Yield: 204 mg, 76 %; MP. 210 °C; White solid; H-NMR (400
1
MHz, DMSO-d6): δ ppm : 4.315-4.329 (d, 2H, -CH2-, J=5.6 Hz),
7.244-7.404 (m, 6H, Ar), 7.473-7.525 (m, 1H, Ar), 7.681-7.708
(m, 1H, Ar), 7.997-8.034 (m, 1H, -NH-), 8.609 (s, 1H, -NH-); 13C-
NMR (400 MHz, DMSO-d6): δ ppm : 48.024, 107.830, 120.993,
123.815, 124.077, 126.344, 126.568, 128.514, 128.582,
131.939, 132.308, 133.418, 144.557, 144.713, 159.745,
160.212, 162.615; HRMS: m/z calculated for [C15H12FN3O+H+] =
270.1037: found = 270.1039.
1-(3-bromophenyl)-3-(4-chloro-2-cyanophenyl)urea (3q)
1
Yield: 279 mg, 80 %; MP. 183 °C; White solid; H-NMR (400
1-(2-cyanophenyl)-3-propylurea (3w)
Yield: 154 mg, 76 %; MP. 199 °C; White solid; H-NMR (400
MHz, DMSO-d6): δ ppm : 7.165-7.180 (d, 1H, Ar, J=6.0 Hz),
7.224-7.262 (t, 1H, Ar, J=7.6 Hz), 7.313 (s, 1H, Ar), 7.685-7.705
(d, 1H, Ar, J=8.0 Hz), 7.844 (s, 1H, Ar), 7.919 (s, 1H, Ar), 7.987-
8.008 (d, 1H, Ar, J=8.4 Hz), 9.160 (s, 1H, -NH-), 9.808 (s, 1H, -
NH-); 13C- NMR (400 MHz, DMSO-d6): δ ppm : 104.320,
116.063, 117.736, 121.180, 122.212, 123.486, 125.490,
127.154, 131.269, 132.641, 134.470, 141.174, 141.213,
152.236; HRMS: m/z calculated for [C14H9BrClN3O+H+] =
349.9690: found = 349.9681.
1
MHz, DMSO-d6): δ ppm : 0.853-0.888 (t, 3H, -CH3, J=7.2 Hz),
1.412-1.462 (m, 2H, -CH2-), 3.037-3.051 (d, 2H, -CH2-, J=5.6 Hz),
6.968 (s, 1H, Ar), 7.041-7.076 (t, 1H, Ar, J=6.8 Hz), 7.525-7.562
(t, 1H, Ar, J=7.6 Hz), 7.637-7.655 (d, 1H, Ar, J=7.2 Hz), 8.039-
8.059 (d, 1H, - NH-, J=8.0 Hz), 8.412 (s, 1H, -NH-); 13C- NMR
(400 MHz, DMSO-d6): δ ppm : 11.805, 23.149, 41.401, 101.216,
117.503, 121.005, 122.474, 133.390, 134.266, 143.324,
154.911; HRMS: m/z calculated for [C11H13N3O+H+] = 204.1131:
found = 204.1136.
1-(3-bromophenyl)-3-(2-cyano-4-fluorophenyl)urea (3r)
Yield: 256mg, 77 %; MP. 182 °C; White solid; 1H-NMR (400
MHz, DMSO-d6): δ ppm : 7.157-7.175 (d, 1H, Ar, J=7.2 Hz),
7.220-7.307 (m, 2H, Ar), 7.525-7.562 (t, 1H, Ar, J=8.0 Hz),
7.756-7.770 (d, 1H, Ar, J=5.6 Hz), 7.840 (s, 1H, Ar), 7.935-7.969
(m, 1H, Ar), 8.797 (s, 1H, -NH-), 9.475 (s, 1H, -NH-); 13C- NMR
(400 MHz, DMSO-d6): δ ppm : 104.971, 105.069, 116.248,
117.688, 119.565, 119.828, 121.122, 121.842, 122.066,
122.202, 124.926, 125.004, 125.344, 131.250, 138.780,
141.359, 152.576, 156.312, 158.725; HRMS: m/z calculated for
[C14H9BrFN3O+H+] = 333.9991: found = 333.9997.
1-(2-cyano-4-fluorophenyl)-3-propylurea (3x)
Yield: 164 mg, 74 %; MP. 204 °C; White solid; H-NMR (400
1
MHz, DMSO-d6): δ ppm : 0.863-0.900 (t, 3H, -CH3, J = 7.6 Hz),
1.423-1.476 (m, 2H, -CH2-), 3.032-3.079 (m, 2H, -CH2-), 6.913
(s, 1H, Ar), 7.478-7.499 (t, 1H, Ar, J=2.4 Hz), 7.665-7.692 (m,
1H, Ar), 7.987-8.022 (m, 1H, -NH-), 8.465 (s, 1H, -NH-); 13C-
NMR (400 MHz, DMSO-d6): δ ppm : 16.395, 27.787, 46.059,
107.392, 121.042, 123.776, 124.029, 126.354, 126.578,
128.271, 144.762, 159.628, 160.046, 162.430; HRMS: m/z
calculated for [C11H12FN3O+H+] = 222.1042: found = 222.1047.
1-(3-chlorophenyl)-3-(2-cyano-4-fluorophenyl)urea (3s)
1
Yield: 234 mg, 81 %; MP. 198 °C; White solid; H-NMR (400
MHz, DMSO-d6): δ ppm : 7.050-7.069 (d, 1H, Ar, J=7.6 Hz),
7.257-7.349 (m, 2H, Ar), 7.547-7.589 (m, 1H, Ar), 7.710 (s, 1H,
Ar), 7.759-7.780 (d, 1H, Ar, J=8.4 Hz), 7.962-7.997 (m, 1H, Ar),
8.785 (s, 1H, -NH-), 9.474 (s, 1H, -NH-); 13C- NMR (400 MHz,
6 | J. Name., 2012, 00, 1-3
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Organic & Biomolecular Chemistry
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Journal Name
ARTICLE
Harsha, N. C. Sandhya, A. B. Ramesha, K. Mantelingu
and K. S. Rangappa, New J. Chem., 2015,Vi3ew9,Ar8ti3cl9e 7O;nli(nfe)
H. A. Swarup, Kemparajegowda,DKO.I:M10a.1n0t3e9l/iDn0gOuBa0n0d118KJ.
S. Rangappa, Chemistry Select, 2018, 3, 703; (g) V. K.
Gopinatha, H. A. Swarup, S. C. Raghavan, K. Mantelingu
and K. S. Rangappa, Synlett, 2019, 30, 2004; (h) S.
V. Kumar, S. K. Yadav, B. Raghava, B. Saraiah, H. Ila,
K. S. Rangappa and A. Hazra, The Journal of Organic
Chemistry, 2013, 78(10), 4960; (i) A. Sebastian, V.
Pandey, C. D. Mohan, Y. T. Chia, S. Rangappa, J. Mathai,
Basappa, P. E. Lobie and K. S. Rangappa, ACS
Omega, 2016, 1(6), 1412; (j) V. Pandey, B. Wang, C. D.
Mohan, A. R. Raquib, S. Rangappa, V. Srinivasa, J. E.
Fuchs, K. S. Girish, T. Zhu, A. Bender, L. Ma, Z.
Yin, Basappa, K. S. Rangappa and P. E. Lobie, PNAS,
2018, 115 (44), E10505.
Conclusion
Herein, we are reporting a straight forward protocol for the
synthesis of o-ureidobenzonitrile derivatives at ambient
conditions using inexpensive and readily available starting
materials. The substrate scope for this method is very broad
and yields are excellent. The synthesized products can serve as
precursors for many cyclized products like quinazolines and
quinazolinones. Utilization of the above unique reaction path
to explore some new kinds of reaction and further extension
of the substrate scope to synthesize derivatives of biological
interest and their biological studies are under progress.
11. (a) O. Obaiah, N. N, Kebbahalli, R. M. Goravanahalli, P.
S. Chottanahalli, R. S. Kanchugarakoppal and M.
Kempegowda, European Journal of Chemistry, 2014, 5
(4), 671; (b) G. M. Raghavendra, C. S. Pavan Kumar, G.
P. Suresha, K. S. Rangappa, K. Mantelingu, Chinese
Chemical Letters, 2015, 26, 963; (c) G. M. Raghavendra.
K. N. Nandeesha, N. C. Sandhya, K. S. Rangappa, K.
Mantelingu, Int. J. Chem.,2014, 35(2), 1634.
12. K. P. Rakesh, A. B. Ramesha, C. S. Shantharam, K.
Mantelingu and N. Mallesha, RSC Adv., 2016, 6,
108315.
13. Taylor and E. Curtis, Tetrahedron, 1967, 23(5), 2081.
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of Sulfur Chemistry, 2011, 32(6), 171.
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Pavan Kumar, N. C. Sandhya, M. N. Kumara, K.
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48375; (d) D. R. Guda, H. M. Cho and M. E.Lee, RSC
Adv., 2013, 3, 7684.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
The author S.S thank the UGC, New Delhi for the financial
support in the form of UGC-JRF/SRF fellowship. Financial
support from the Minor Research Project, University of Mysore
(grant No. DV6/ 375/ MRP/ 2017-18, dated: 12–02-2018) and
VGST Project (Grant No. Ksteps/ VGST/ GRD-681/ KFIST(L1)/
2018, dated: 27-08-2018) is gratefully acknowledged.
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J. Name., 2013, 00, 1-3 | 7
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Organic & Biomolecular Chemistry
Page 8 of 8
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DOI: 10.1039/D0OB00118J
I2 – Catalysed Transformation of o-Aminobenzamide to o-Ureidobenzonitrile Using
Isothiocyanates
SadashivamurthyShamanth,aNagarajuChaithra,aMaheshaGurukiran,aMaheshaMamatha,b N. K. Lokanath,cKanchugarakoppal S
Rangappa*a andKempegowdaMantelingu*a
a.DOS in Chemistry, Manasagangotri, University of Mysore, Mysuru-570006, Karnataka, India.
b.SRSMNGFG College, Barkur-576210, Udupi Dist., Karnataka, India.
c. DOS in Physics, Manasagangotri, University of Mysore, Mysuru-570006, Karnataka, India.
E-mail: kmlingu@gmail.com, rangappaks@gmail.com
Tel: +91 9743708962; +91 821 2419497