Synthesis of functionalized quinoline derivatives via intramolecular C–H activation reactions of N-sulfonylamidines and isocyanides

Article abstract of DOI:10.1007/s00706-020-02684-5

Abstract: A novel class of substituted quinolines was synthesized through a one-pot, four-component sequential reaction by intramolecular C–H activation of isocyanides with N-sulfonylamidines, catalyzed by copper(I) iodide and l-proline as a ligand in acetonitrile at room temperature. The readily available starting materials, no need for column chromatography, mild catalytic conditions, and moderate to high yields are important features of this simple one-pot reaction. Graphic abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s00706-020-02684-5

Monatshefte für Chemie - Chemical Monthly
https://doi.org/10.1007/s00706-020-02684-5
ORIGINAL PAPER
Synthesis of functionalized quinoline derivatives via intramolecular
C–H activation reactions of N‑sulfonylamidines and isocyanides
Anna Sedaghat1 · Manijeh Nematpour1 · Maryam Bayanati1 · Sayyed Abbas Tabatabai1
Received: 18 December 2019 / Accepted: 7 September 2020
© Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract
A novel class of substituted quinolines was synthesized through a one-pot, four-component sequential reaction by intramo-
lecular C–H activation of isocyanides with N-sulfonylamidines, catalyzed by copper(I) iodide and l-proline as a ligand in
acetonitrile at room temperature. The readily available starting materials, no need for column chromatography, mild catalytic
conditions, and moderate to high yields are important features of this simple one-pot reaction.
Graphic abstract
Keywords C–H activation · Copper catalysis · Sulfonylketenimines · Quinolines · Isocyanide
Introduction
In the other hand, there are numbers of sulfa drugs with
sulfonamide moiety including sulfa methoxazole, an antibi-
otic [9], dapsone, an antibacterial agent against leprosy and
autoimmune disease [10], hydrochlorothiazide, a diuretic
for hypertension [11], acetazolamide, a carbonic anhydrase
inhibitor for the treatment of glaucoma [12].
Quinolines are ubiquitous heterocyclic core that occur in a
wide range of drugs and natural products. Some of remark-
able examples are chloroquine [1], ciprofoxazin [2, 3], and
iodoquinol [4], used widely against malaria, broad range
of bacterial infections and amebiasis, respectively. Further-
more, many attractive 4-aminoquinolines derivatives to con-
trol pain and infammation [5], cancer [6, 7], and PDE5 [8]
are also reported (Fig. 1).
Traditionally drug design was based on the synthesis of
lead compounds with high selectivity and potency [13], but
this methodology has been challenged by varied causative
factors involved in diseases [14]. So, multi-acting of hybrid
compounds in the feld of poly pharmacology has grown at
a remarkable pace in past two decades [15]. The intrinsic
benefts of multicomponent reactions in modern organic syn-
thesis have led to exploit the copper-catalyzed azide-alkyne
cycloaddition (CuAAC) in the felds of combinatorial chem-
istry and multi-target drug discovery (MTDD) [16].
Electronic supplementary material The online version of this
article (https://doi.org/10.1007/s00706-020-02684-5) contains
supplementary material, which is available to authorized users.
* Sayyed Abbas Tabatabai
sa_tabatabai@sbmu.ac.ir
We were eager extending our approach to combine the
chemistry of CuAAC with intramolecular C–H activation
to synthesis of novel functionalized quinolines carrying
two pharmacophores: 4-aminoquinoline and 2-sulfonamide
1
Department of Pharmaceutical Chemistry, School
of Pharmacy, Shahid Beheshti University of Medical
Sciences, Tehran, Iran
Vol.:(0123456789)
1 3

A. Sedaghat et al.
Fig. 1 Some medicinally attrac-
tive molecules
moiety. To the best of our knowledge, quinolines with these
two important functional groups have not been reported, so
far.
and the results are summarized in the Table 1. The observa-
tions showed that among the copper salts including CuI,
CuBr, CuCl, Cu(OAc)2, and CuSO4 (10 mol% amount), CuI
presents the most catalytic efect. MeCN was the optimal
solvent and, out of the bases tested, Cs2CO3 gave the best
results.
The metal-catalyzed multicomponent reaction based on
isocyanides was previously reported [17, 18]. The intramo-
lecular heterofunctionalization of sp2 C–H bond in aromatic
ring is an ideal strategy to achieve fused-ring complex het-
erocycles, especially those containing nitrogen with higher
atom efciency, and synthetic easiness approach [19–24].
Our research group discovered a novel reaction that cop-
per plays a dual catalytic role in click reaction along with sp2
C–H activation. Herein, we report a novel four-component
sequential reaction using copper catalyst to synthesis func-
tionalized quinolines with both 4-amino and 2-sulfonamide
moieties.
In practice, the optimized conditions were applied to syn-
thesise quinoline derivatives 7 from sulfonylazide, various
isocyanide, acetylene, and anilines with diferent electron-
withdrawing or electron-donating substituents (see Table 2).
The structures of compounds 7a–7j were assigned by
1
IR, H NMR, 13C NMR spectroscopy, and direct mass
1
spectrometry. For example, the H NMR spectrum of 7a
exhibited three singlets: one for methyl group at δ = 3.07
and two for NH groups at 6.57 ppm and 8.65 ppm, which
are representative of 4-amino and 2-sulfonamide moiety,
respectively. These results along with essential features of
multiplets of the phenyl groups determined the target struc-
ture. The 13C NMR spectrum of 7a exhibited 16 signals, in
agreement with the proposed structure. The mass spectrum
of 7a displayed a molecular ion at m/z=389 corresponding
to [M+H]+.
Results and discussion
In contrast to conventional click chemistry in which
1,2,3-triazoles is formed, the reaction of the terminal
alkynes 1 with the sulfonylazides 2 only afords unstable
triazole intermediates, so smoothly resulting in ketenimine
3 upon release of molecular nitrogen. The reaction of in situ
prepared N-sulfonylketenimine intermediate 3 with aromatic
amines 4 afords the corresponding amidines 5 that under-
goes further chemistry to trap isocyanide 6 and ultimately
lead to the production of functionalized quinolines 7 in
sequential reaction as shown in Scheme 1.
The reaction is probably carried out according to the
mechanism shown in Scheme 2. It is thought that amidine
derivative 6 is formed from aniline 4 and N-sulfonylketen-
imines intermediate 3, and CuI-proline adjunct initially
produced the fve-membered chelate A. Then, the oxida-
tive addition of the chelated Cu(I) with amidine derivative
6 in the presence of Cs2CO3 leads to the intermediate B
in which the partially negative charge on proximal Cβ to
amidine and the isocyanide carbon atom might coordinate
with the copper. A reductive elimination reaction of B then
afords 8 that leads to the quinoline 7 through tautomeriza-
tion mechanism and the catalyst chelate A is regenerated
Methane sulfonylazide, phenyl isocyanide, phenylacety-
lene, and aniline were initially used as model of substrates to
optimize the reaction conditions, in which two frst reactants
were synthesized separately. The efects of diferent cata-
lysts, solvents, and bases on the reaction yield were tested
1 3

Synthesis of functionalized quinoline derivatives via intramolecular C–H activation reactions…
Scheme 1
Table 1 The optimization reaction conditions for the synthesis of
N-[3-phenyl-4-(phenylamino)quinolin-2-yl]methanesulfonamide
Table 2 Synthesis of various quinoline derivatives
Entry
Catalyst
Solvent
Base
Yield /%a
1b
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
CuI
MeCN
MeCN
DMF
DMF
THF
Cs2CO3
NaOH
87
60
38
51
22
51
59
41
45
28
26
44
20
24
–-
CuI
CuI
CuI
CuCl
CuCl
CuBr
CuBr
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
CuSO4
CuSO4
CuSO4
Cu
KOt-Bu
Cs2CO3
KOt-Bu
K2CO3
Cs2CO3
K2CO3
Cs2CO3
KOt-Bu
Cs2CO3
K2CO3
Cs2CO3
NaOH
Compound
R
R1
R2
R3
Yield /%
THF
MeCN
DMF
MeCN
DMF
THF
MeCN
THF
DMF
MeCN
DMF
7a
7b
7c
7d
7e
7f
7 g
7 h
7i
Ph
Me
H
H
H
NO2
Br
H
Ph
87
76
71
84
80
76
88
n-Bu Ph
n-Bu 4-Me-C6H4
t-Bu
t-Bu
t-Bu
Ph
t-Bu
Ph
Ph
Ph
n-Pr
Ph
Ph
Ph
Ph
4-Cl-C6H4
Me
Me
Ph
H
4-Me-C6H4 NO2
4-Br-C6H4
Me
4-Br-C6H4 83
4-Cl-C6H4 78
Cs2CO3
K2CO3
Me
OMe Ph
Cu
–-
7j
74
aReaction time 5 h
b5 mol% catalyst, reaction time was 10 h
Conclusion
again. Interestingly, the lack of formation of the product 9
indicates that this reaction is not carried out through previ-
ously observed mechanisms in which the amidine nitrogen
atom and the isocyanide carbon atom were coordinated to
the copper. The structure 9 can be ruled out on the basis of
1H NMR and 13C NMR spectra of the products.
In this study, we have developed a novel one-pot synthe-
sis of pharmacologically attractive quinolines through a
four-component, intramolecular, C–H activation reaction
of isocyanides with adducts of anilines and N-sulfonylke-
tenimines, catalyzed by copper(I) iodide in MeCN at room
1 3

A. Sedaghat et al.
Scheme 2
temperature. The abundance of the starting material, the
mild conditions, and the ease of purifcation resulting in
high yields make this reaction a valuable method for the
synthesis of various quinoline derivatives carrying two
pharmacophores.
as the ligand in 2 cm3 MeCN was slowly added to the frst
reaction container and the reaction mixture was stirred at
room temperature for 5 h. After completion of the reac-
tion [TLC (AcOEt/ hexane 1:4) monitoring], the mixture
was diluted with 2 cm3 CH2Cl2 and 3 cm3 aqueous NH4Cl
solution, stirred for 30 min. The layers were separated and
the aqueous layer was extracted with 2 cm3 of CH2Cl2 and
the combined organic fractions were dried (over anhydrous
Na2SO4) and concentrated under reduced pressure. The
resulting solid was isolated by fltration and purifed with
n-hexane/ AcOEt.
Experimental
All were reagents purchased from Merck Company. Melting
points: Electrothermal 9100 apparatus; corrected. IR Spec-
tra: Shimadzu-IR-460 spectrometer, in KBr; in cm−1, CHN
analysis: Heraeus CHN-O-Rapid analyzer. 1H and 13C NMR
Spectra: Bruker DRX-500 Avance instrument, in CDCl3 at
500.1 and 125.7 MHz, resp.; s=singlet, d=doublet, t=tri-
plet, m=multiplet, δ in parts per million, J in hertz. EI-MS:
Finnigan-MAT-8430 at 70 eV; in m/z (rel. %).
N‑[3‑Phenyl‑4‑(phenylamino)quinolin‑2‑yl]methanesul‑
fonamide (7a, C22H19N3O2S) White powder; yield: 0.34 g
(87%); m.p.: 177–179 °C; IR (KBr): ꢀ =3322, 3315, 1604,
1
1385, 1160 cm−1; H NMR (500 MHz, CDCl3): δ = 3.07
(s, 3H, Me), 6.57 (s, 1H, NH), 7.30–7.36 (m, 4H, Ph), 7.40
3
(t, J = 7.7 Hz, 1H, Ar), 7.47–7.53 (m, 6H, Ph), 7.63 (t,
3
3
General procedure for preparation of compounds 7
J = 7.9 Hz, 1H, Ar), 7.92 (d, J = 7.9 Hz, 1H, Ar), 7.98
(d, 3 J=7.9 Hz, 1H, Ar), 8.65 (s, 1H, NH) ppm; 13C NMR
(125.7 MHz, CDCl3): δ = 31.3 (Me), 127.5 (2 CH), 128.7
(2 CH), 129.2 (2 CH), 129.3 (2 CH), 130.7 (CH), 132.6 (2
CH), 133.0 (2 CH), 134.4 (CH), 136.2 (C), 138.8 (C), 142.1
(C), 147.2 (C), 150.1 (C), 164.4 (C), 167.4 (C) ppm; MS:
To a mixture of sulfonylazide 2 (1.2 mmol), alkyne 1
(1.0 mmol), CuI (0.1 mmol), and Et3N (1.0 mmol) in 2
cm3 MeCN was slowly added aniline 4 (1.0 mmol) and
stirred for 10 min. Thereafter, a mixture of isocyanide 6
(1.5 mmol), Cs2CO3 (1.5 mmol), and 20 mol% of L-proline
1 3

Synthesis of functionalized quinoline derivatives via intramolecular C–H activation reactions…
m/z (%)=389 (M+, 2), 310 (27), 295 (33), 220 (21), 94 (50),
N‑[6‑Bromo‑3‑phenyl‑4‑(phenylamino)quinolin‑2‑yl]meth‑
77 (100).
anesulfonamide (7e, C22H18BrN3O2S) White powder; yield:
0.37 g (80%); m.p.: 177–180 °C; IR (KBr): ꢀ =3311, 3215,
1
N‑[3‑Butyl‑4‑(tert‑butylamino)quinolin‑2‑yl]benzenesul‑
fonamide (7b, C23H29N3O2S) White powder; yield: 0.31 g
(76%); m.p.: 155–157 °C; IR (KBr): ꢀ =3312, 3220, 1600,
1599, 1380, 1134 cm−1; H NMR (500 MHz, CDCl3):
δ=3.68 (3H, s, Me), 6.00 (s, 1H, NH), 7.31–7.35 (m, 5H,
Ar), 7.48 (d, 3J=7.8 Hz, 2H, Ar), 7.60 (t, 3J=7.8 Hz, 1H,
Ar), 7.65 (t, 3J=7.9 Hz, 1H, Ar), 7.67 (d, 3J=7.9 Hz, 2H,
Ar), 8.04 (d, 3J=7.8 Hz, 1H, Ar), 8.32 (d, 3J=7.8 Hz, 1H,
Ar), 9.02 (s, 1H, NH) ppm; 13C NMR (125.7 MHz, CDCl3):
δ=30.8 (Me), 122.6 (CH), 123.2 (C), 123.8 (2 CH), 129.2
(C), 129.4 (2 CH), 130.0 (2 CH), 130.1 (2 CH), 130.9 (2
CH), 131.3 (2 CH), 133.3 (C), 140.2 (C), 142.4 (C), 147.9
(C), 159.2 (C), 167.0 (C) ppm; MS: m/z (%)=468 (M+, 9),
388 (44), 374 (10), 361 (21), 92 (100), 78 (65).
1
1382, 1167 cm−1; H NMR (500 MHz, CDCl3): δ = 0.96
(3H, t, 3J=6.7 Hz, Me), 1.24–1.29 (2H, m, CH2), 1.30–1.34
(2H, m, CH2), 2.17 (9H, s, CMe3), 2.20 (2H, t, 3J=6.7 Hz,
CH2), 6.00 (s, 1H, NH), 7.63 (t, 3J=7.8 Hz, 2H, Ar), 7.70
3
(t, J = 7.8 Hz, 1H, Ar), 7.75–7.80 (m, 2H, Ph), 8.06 (d,
3
3J = 7.6 Hz, 2H, Ar), 8.10 (d, J = 7.9 Hz, 1H, Ar), 8.40
(d, 3J=7.9 Hz, 1H, Ar), 8.95 (s, 1H, NH) ppm; 13C NMR
(125.7 MHz, CDCl3): δ = 14.6 (Me), 19.2 (CH2), 22.9
(CMe3), 30.8 (CH2), 31.6 (CH2), 58.3 (CMe3), 128.0 (2 CH),
128.4 (2 CH), 129.4 (2 CH), 129.6 (CH), 130.2 (CH), 130.3
(CH), 130.4 (C), 136.5 (C), 144.0 (C), 145.4 (C), 161.2 (C),
163.0 (C) ppm; MS: m/z (%)=411 (M+, 2), 354 (22), 339
(29), 334 (37), 270 (100), 141 (50), 77 (40).
N‑[4‑(tert‑Butylamino)‑3‑propylquinolin‑2‑yl]methanesul‑
fonamide (7f, C17H25N3O2S) Cream powder; yield: 0.25 g
(76%); m.p.: 122–125 °C; IR (KBr): ꢀ =3311, 3210, 1577,
1
1380, 1155 cm−1; H NMR (500 MHz, CDCl3): δ = 0.90
3
(3H, t, J = 6.8 Hz, Me), 1.25–1.30 (2H, m, CH2), 1.90
N‑[3‑Butyl‑4‑(tert‑butylamino)quinolin‑2‑yl]‑4‑methylben‑
zenesulfonamide (7c, C24H31N3O2S) Cream powder; yield:
0.30 g (71%); m.p.: 138–140 °C; IR (KBr): ꢀ =3311, 3225,
(9H, s, CMe3), 2.12 (2H, t, 3J=6.8 Hz, CH2), 3.24 (3H, s,
3
Me), 6.01 (s, 1H, NH), 7.67 (t, J = 7.8 Hz, 1H, Ar), 7.76
(t, 3J=7.8 Hz, 1H, Ar), 8.09 (d, 3J=7.9 Hz, 1H, Ar), 8.40
(d, 3J=7.9 Hz, 1H, Ar), 9.22 (s, 1H, NH) ppm; 13C NMR
(125.7 MHz, CDCl3): δ = 14.6 (Me), 19.1 (CH2), 22.9
(CMe3), 29.9 (Me), 31.0 (CH2), 57.9 (CMe3), 121.3 (CH),
124.4 (CH), 129.4 (CH), 130.4 (CH), 132.5 (C), 140.1 (C),
144.1 (C), 162.0 (C), 167.1 (C) ppm; MS: m/z (%) = 335
(M+, 8), 292 (33), 263 (10), 256 (21), 72 (50), 43 (68).
1
1567, 1380, 1164 cm−1; H NMR (500 MHz, CDCl3):
δ=0.95 (3H, t, 3 J=6.8 Hz, Me), 1.26–1.32 (2H, m, CH2),
1.33–1.36 (2H, m, CH2), 1.94 (9H, s, CMe3), 2.18 (2H, t,
3 J =6.8 Hz, CH2), 2.37 (3H, s, Me), 6.01 (s, 1H, NH), 7.41
(d, 3J=7.9 Hz, 2H, Ar), 7.63 (t, 3J=7.9 Hz, 1H, Ar), 7.72
(t, 3J=7.8 Hz, 1H, Ar), 7.92 (d, 3J=7.8 Hz, 2H, Ar), 8.06
(d, 3J=7.9 Hz, 1H, Ar), 8.37 (d, 3J=7.9 Hz, 1H, Ar), 8.03
(s, 1H, NH) ppm; 13C NMR (125.7 MHz, CDCl3): δ=14.7
(Me), 19.2 (CH2), 22.5 (CH2), 23.0 (CMe3), 30.8 (Me), 31.7
(CH2), 58.9 (CMe3), 127.1 (CH), 128.3 (2 CH), 129.7 (CH),
130.2 (CH), 130.9 (CH), 131.4 (C), 132.7 (2 CH), 134.6 (C),
141.8 (C), 142.7 (C), 145.8 (C), 160.7 (C), 162.1 (C) ppm;
MS: m/z (%)=425 (M+, 9), 368 (24), 353 (30), 334 (36), 91
(100), 78 (60).
N‑[3‑Phenyl‑4‑(phenylamino)quinolin‑2‑yl]benzenesul‑
fonamide (7g, C27H21N3O2S) White powder; yield: 0.40 g
(88%); m.p.: 145–147 °C; IR (KBr): ꢀ =3311, 3225, 1612,
1380, 1163 cm−1; 1H NMR (500 MHz, CDCl3): δ=6.07 (s,
1H, NH), 7.30–7.37 (m, 4H, Ph), 7.48 (d, 3J=7.7 Hz, 2H,
3
Ar), 7.59 (t, J = 7.9 Hz, 1H, Ar), 7.60–7.66 (m, 6H, Ph),
7.75 (t, 3J = 7.9 Hz, 1H, Ar), 8.00–8.06 (m, 4H, Ph), 8.29
(d, 3J=7.9 Hz, 1H, Ar), 9.21 (s, 1H, NH) ppm; 13C NMR
(125.7 MHz, CDCl3): δ=127.2 (2 CH), 128.1 (2 CH), 128.9
(CH), 129.2 (2 CH), 130.2 (2 CH), 130.7 (2 CH), 131.6
(2 CH), 132.0 (CH), 133.0 (2 CH), 133.2 (C), 133.5 (C),
135.9 (CH), 136.4 (CH), 138.8 (C), 139.9 (C), 140.1 (C),
145.4 (C), 148.7 (C), 160.9 (C), 163.4 (C) ppm; MS: m/z
(%)=451 (M+, 8), 374 (22), 352 (55), 310 (20), 141 (100),
92 (50), 77 (66).
N‑ [ 4 ‑ ( ter t‑ B u t y l a m i n o ) ‑ 6 ‑ n i t r o ‑ 3 ‑ p h e n y l q u i ‑
n o l i n ‑ 2 ‑ y l ] ‑ 4 ‑ c h l o r o b e n z e n e s u l fo n a m i d e ( 7 d,
C25H23ClN4O4S) Pale yellow powder; yield: 0.43 g (84%);
m.p.: 182–184 °C; IR (KBr): ꢀ =3311, 3212, 1600, 1585,
1
1343, 1169 cm−1; H NMR (500 MHz, CDCl3): δ = 2.47
(9H, s, CMe3), 6.23 (s, 1H, NH), 7.25–7.33 (m, 4H, Ar),
7.38–7.41 (m, 4H, Ar), 7.49 (d, 3 J=7.8 Hz, 2H, Ar), 7.82
(d, 3 J=7.8 Hz, 1H, Ar), 7.91 (d, 3J=7.8 Hz, 1H, Ar), 9.12
(s, 1H, NH) ppm; 13C NMR (125.7 MHz, CDCl3): δ=27.1
(CMe3), 52.6 (CMe3), 127.5 (2 CH), 128.0 (2 CH), 128.7
(2 CH), 129.2 (CH), 130.7 (CH), 130.8 (2 CH), 132.5 (C),
135.9 (2 CH), 136.5 (C), 137.4 (C), 142.1 (C), 144.4 (C),
146.7 (C), 147.2 (C), 166.3 (C), 167.2 (C) ppm; MS: m/z
(%)=510 (M+, 2), 433 (44), 399 (22), 335 (29), 111 (100),
92 (51), 77 (42).
N‑[4‑[(4‑Bromophenyl)amino]‑6‑nitro‑3‑phenylqui‑
n o l i n ‑ 2 ‑ y l ] ‑ 4 ‑ m e t hy l b e n ze n e s u l fo n a m i d e ( 7 h ,
C28H21BrN4O4S) Pale yellow powder; yield: 0.49 g (83%);
m.p.: 180–183 °C; IR (KBr): ꢀ =3313, 3300, 1612, 1505,
1324, 1144 cm−1; 1H NMR (500 MHz, CDCl3): δ=2.35 (s,
3
3H, Me), 6.00 (s, 1H, NH), 7.21 (d, J = 7.7 Hz, 2H, Ar),
7.29–7.31 (m, 3H, Ph), 7.40 (d, 3J=7.7 Hz, 2H, Ar), 7.53
1 3

A. Sedaghat et al.
(d, 3J=7.9 Hz, 2H, Ar), 7.57 (t, 3J=7.7 Hz, 1H, Ar), 7.62
(d, 3J=7.8 Hz, 2H, Ar), 7.91 (d, 3J=7.8 Hz, 2H, Ar), 8.02
(d, 3J=7.9 Hz, 1H, Ar), 8.26 (d, 3J=7.9 Hz, 1H, Ar), 9.00
(s, 1H, NH) ppm; 13C NMR (125.7 MHz, CDCl3): δ=30.8
(Me), 127.2 (C), 127.9 (CH), 128.1 (2 CH), 129.4 (CH),
130.2 (2 CH), 130.9 (2 CH), 131.4 (2 CH), 132.0 (CH),
133.2 (CH), 133.8 (2 CH), 134.5 (2 CH), 135.2 (CH), 136.6
(2 CH), 138.9 (C), 139.9 (C), 140.0 (C), 142.8 (C), 148.0
(C), 158.0 (C), 166.0 (C) ppm; MS: m/z (%)=589 (M+, 10),
496 (15), 433 (18), 154 (74), 107 (100), 91 (50), 77 (61).
Acknowledgements This work was supported by the research council
of the school of pharmacy, Shahid Beheshti University of medical sci-
ences. [Grant No. 10445].
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1158 cm−1; H NMR (500 MHz, CDCl3): δ = 2.56 (s, 3H,
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Me), 5.88 (s, 1H, NH), 7.25–7.30 (m, 5H, Ph), 7.32–7.36 (m,
4H, Ph), 7.48 (s, 1H, Ph), 7.49 (d, 3J=7.7 Hz, 2H, Ar), 7.60
(d, 3J=7.9 Hz, 1H, Ar), 7.74 (t, 3J=7.7 Hz, 1H, Ar), 8.05
(d, 3J=7.9 Hz, 2H, Ar), 8.87 (s, 1H, NH) ppm; 13C NMR
(125.7 MHz, CDCl3): δ=28.3 (Me), 126.1 (2 CH), 127.4 (2
CH), 127.8 (CH), 129.2 (CH), 130.0 (CH), 130.1 (2 CH),
132.6 (2 CH), 132.9 (C), 133.1 (CH), 133.9 (2 CH), 135.7 (2
CH), 135.9 (C), 136.1 (C), 138.4 (C), 139.8 (C), 140.1 (C),
144.8 (C), 146.1 (C), 151.1 (C), 160.1 (C), 166.1 (C) ppm;
MS: m/z (%)=578 (M+, 2), 499 (20), 422 (19), 358 (30), 218
(61), 154 (100), 92 (51), 77 (97).
8. Bi Y, Stoy P, Adam L, He B, Krupinski J, Normandin D (2004)
Bioorg Med Chem Lett 14:1577
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12. Grant WM, Trotter RR (1954) AMA Arch Ophthalmol 51:735
13. Hughes JP, Rees SS, Kalindjian SB, Philpott KL (2011) Br J Phar-
macol 162:1239
14. Ramsay RR, Popovic-Nikolic MR, Nikolic K, Uliassi E, Bolog-
nesi ML (2018) Clin Transl Med 7:3
15. Bolognesi ML, Cavalli A (2016) ChemMedChem 11:1190
16. Meldal M, Tomøe CW (2008) Chem Rev 108:2952
17. Sadjadi S, Heravi MM, Nazari N (2016) RSC Adv 6:53203
18. Nematpour M, Rezaee E, Jahani M, Tabatabai SA (2019) J Iran
Chem Soc 16:603
N‑[6‑Methoxy‑3‑phenyl‑4‑(phenylamino)quinolin‑2‑yl]‑
methanesulfonamide (7j, C23H21N3O3S) Cream pow-
der; yield: 0.35 g (84%); m.p.: 152–155 °C; IR (KBr):
19. Yavari I, Ghazanfarpour-Darjani M, Nematpour M (2015) Tetra-
hedron Lett 56:2416
ꢀ = 3300, 3215, 1543, 1305, 1163 cm−1 1H NMR
;
20. Nematpour M, Rezaee E, Jahani M, Tabatabai SA (2018) Tetra-
hedron Lett 59:2054
(500 MHz, CDCl3): δ = 2.76 (s, 3H, Me), 3.88 (s, 3H,
3
21. Nematpour M, Rezaee E, Tabatabai SA, Jahani M (2017) Synlett
28:1441
OMe), 6.06 (s, 1H, NH), 7.19 (d, J = 7.7 Hz, 2H, Ar),
7.27–7.31 (m, 4H, Ph), 7.36 (d, 3J = 7.7 Hz, 1H, Ar), 7.45
22. Xie X, Gai G, Ma D (2005) Org Lett 7:4693
23. Nazari M, Nematpour M, Rezaee E, Jahani M, Tabatabai SA
(2019) J Sulfur Chem 39:646
3
(d, J = 7.7 Hz, 2H, Ar), 7.88–7.90 (m, 4H, Ph), 8.18 (s,
1H, NH) ppm; 13C NMR (125.7 MHz, CDCl3): δ = 33.1
(Me), 57.1 (OMe), 126.0 (2 CH), 128.7 (CH), 129.2 (2
CH), 130.0 (CH), 130.6 (CH), 132.5 (CH), 132.8 (2 CH),
133.9 (CH), 134.1 (2 CH), 134.8 (C), 135.5 (C), 135.7
(C), 142.1 (C), 144.9 (C), 151.3 (C), 165.7 (C), 168.0 (C)
ppm; MS: m/z (%) = 419 (M+, 9), 340 (17), 327 (45), 299
(20), 92 (100), 77 (61).
24. Yang D, An B, Wei W, Tian L, Huang B, Wang H (2019) ACS
Comb Sci 17:113
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