Direct coupling of haloquinolines and sulfonyl chlorides leading to sulfonylated quinolines in water

Article abstract of DOI:10.1016/j.tetlet.2018.12.016

A simple and efficient method has been developed for construction of sulfonylated quinolines via coupling of haloquinolines and sulfonyl chlorides in water. The present methodology provides an attractive approach to various sulfonylated quinolines in moderate to good yields with favorable functional group tolerance, which has the advantages of operation simplicity, readily available starting materials, excellent regioselectivity, scale-up synthesis, and organic solvent-free conditions.

Full text of DOI:10.1016/j.tetlet.2018.12.016

Accepted Manuscript
Direct coupling of haloquinolines and sulfonyl chlorides leading to sulfonylated
quinolines in water
Pengli Bao, Leilei Wang, Qishun Liu, Daoshan Yang, Hua Wang, Xiaohui Zhao,
Huilan Yue, Wei Wei
PII:
S0040-4039(18)31448-5
https://doi.org/10.1016/j.tetlet.2018.12.016
TETL 50479
DOI:
Reference:
To appear in:
Tetrahedron Letters
Received Date:
Revised Date:
Accepted Date:
21 October 2018
5 December 2018
7 December 2018
Please cite this article as: Bao, P., Wang, L., Liu, Q., Yang, D., Wang, H., Zhao, X., Yue, H., Wei, W., Direct
coupling of haloquinolines and sulfonyl chlorides leading to sulfonylated quinolines in water, Tetrahedron
Letters (2018), doi: https://doi.org/10.1016/j.tetlet.2018.12.016
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Direct coupling of haloquinolines and sulfonyl chlorides Leave this area blank for abstract info.
leading to sulfonylated quinolines in water
Pengli Bao, Leilei Wang, Qishun Liu, Daoshan Yang, Hua Wang, Xiaohui Zhao, Huilan Yue,
and Wei Wei
A facile protocol for the one-pot synthesis of various sulfonylated quinolines was developed in water under base
and organic solvent-free conditions.

1
Tetrahedron Letters
Direct coupling of haloquinolines and sulfonyl chlorides leading to sulfonylated
quinolines in water
a
a
a
a,c
a
b
Pengli Bao, Leilei Wang, Qishun Liu, Daoshan Yang, Hua Wang, Xiaohui Zhao,* Huilan
b
a,b,c
Yue, and Wei Wei*
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China
Qinghai Provincial Key Laboratory of Tibetan Medicine Research and Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology,
a
b
Chinese Academy of Sciences, Qinghai 810008, China.
c
College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, P. R. China.
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
A simple and efficient method has been developed for construction of sulfonylated quinolines
via coupling of haloquinolines and sulfonyl chlorides in water. The present methodology
provides an attractive approach to various sulfonylated quinolines in moderate to good yields
with favorable functional group tolerance, which has the advantages of operation simplicity,
readily available starting materials, excellent regioselectivity, scale-up synthesis, and organic
solvent-free conditions.
Available online
Keywords:
haloquinolones
sulfonylated quinolines
zinc powder
2
016 Elsevier Ltd. All rights reserved.
sulfonyl chlorides
in water
As one of the most important N-heterocycle structural motifs,
protocol for synthesis of 2-sulfonylquinolinesthe via
quinolines are widely existed in numerous natural products,
bioactive compounds, and advanced functional materials.
sulfonylation of quinoline N-oxides with sulfonyl chlorides and
subsequent reduction. In 2015, Zhao et al. also presented the H-
1
11
Consequently, the construction of valuable functionalized
quinoline derivatives in chemo- and regioselective fashion is a
prominent research topic in synthetic and pharmaceutical
phosphonate-mediated sulfonylation of quinoline N-oxides with
12
sulfonyl chlorides leading to 2-sulfonyl quinolines. Recently,
He and co-workers report an ultrasound accelerated one-pot
synthesis of 2-sulfonylquinolines from quinoline N-oxides with
2
chemistry. Sulfone group represents a class of highly valuable
13
organic functionality, which is often introduced into organic
frameworks to enhance the possible biological activities during
sulfonyl chlorides. Nevertheless, the methods for sulfonylation
of quinoline N-oxides encountered certain drawback of low
regioselectivity. In contrast, the direct sulfonylation of
halogenated quinolines has an advantage of the completely
controllable regioselectivity. Therefore, the development of mild,
convenient and efficient method for regioselective synthesis of
sulfonylated quinolines from haloquinolines and sulfonyl
chlorides is highly desirable.
3
the drug design. In particular, sulfonated quinolines have drawn
increasing attention from chemists owing to their important
4
biological activity and pharmacological value. Generally,
sulfonated quinolines are prepared by the coupling of 2-
5
haloquinoliness with sulfinate and the thioetherification of
6
haloquinolines with thiols and subsequent oxidation. Alternative
methods for the sulfonylation of quinoline N-oxides with sodium
Water is an attractive green solvent for numerous organic
reactions owing to its low cost, natural abundance and eco-
friendly properties. However, to the best of our knowledge,
there is no example of the sulfonylation of haloquinolines with
sulfonyl chlorides in water was reported. As part of our ongoing
7
8
sulfinates and sulfonyl hydrazides have also been developed.
These methods, although effective, require relatively harsh
reaction conditions or tedious operation procedures. In addition,
the sulfonating reagents such as sodium sulfinates and sulfonyl
hydrazides have limited commercial availability, which are
usually synthesized from the corresponding sulfonyl chlorides in
14
1
5
interest in the construction of sulfone-containing compounds
16
and green organic synthesis, herein, we wish to report a simple
and convenient method for the construction of sulfonylated
quinolines from inexpensive and readily available haloquinolines
and sulfonyl chlorides in water (Scheme 1).
9
the presence of sulfinate salts or dangerous hydrazine hydrate
10
under alkaline condition. Recently, the sulfonylation of
quinoline N-oxides with sulfonyl chlorides have been reported. In
2013, Cui’s group developed an elegant copper-catalyzed
Corresponding authors.
E-mail: xhzhao@nwipb.cas.cn,(X. Zhao), weiweiqfnu@163.com ( W. Wei)

2
their electronic characters, 2-chloroquinoline coupled
efficiently with aryl sulfonyl chlorides to deliver the sulfonylated
products in good to excellent yields (3d – 3k). Notably, the
reaction of 2-chloroquinoline with naphthalene-2-sulfonyl
chloride and heterocycle sulfonyl chloride such as 2-
thiophenesulfonyl chloride afforded the desired products (3l and
3
m) in 85% and 81% yields, respectively. It should be noted that
Scheme 1. Synthetic route to sulfonylated quinolines.
this reaction was also extended to aliphatic sulfonyl chlorides
such as benzylsulfochloride, n-propanesulfonyl chloride and
cyclopropylsulfonyl chloride (3n – 3p). Encouraged by these
results, we subsequently turned to haloquinoline substrates.
Delightfully, both substituted 2-chloroquinolines and 4-
chloroquinolines reacted efficiently with tosyl chloride affording
the desired products (3q – 3x) in good to excellent yields.
Moreover, 2-bromoquinoline and 2-iodoquinoline are also
suitable substrates, providing the desired product 3a in good
yields. In addition, 1-chloroisoquinoline could also used in this
reaction to produce the sulfonylated product 3y in 68% yield.
In our initial investigation, the reaction of 2-chloroquinoline
1a) with tosyl chloride (2a) was conducted in the presence of
(
iron powder (1.5 equiv.) in water at 100℃ for 12 h, and a 85%
1
yield (determined by H NMR) of 2a was observed (Table 1,
entry 1). Encouraged by this promising result, various reaction
parameters were screened to optimize the reaction conditions. A
series of cheap metal powders were investigated and zinc powder
was found to be the best choice for this reaction (Table 1, entries
-5). Next, other reaction parameters such as equivalents of 2a,
loading of reductant and reaction temperature were examined
Table 1, entries 6-10). The reaction efficiency was obviously
improved by decreasing the amount of zinc powder to 1.0 equiv
Table 1, entry 6). However, further reduction of zinc powder to
.75 equiv. resulted in a lower yield (Table 1, entry 7). Adjusting
2
13
(
Notably, 4-chloro-2-tosylquinoline 3z was selectively obtained
in 70% yield when the reaction of 2,4-dichloroquinoline and
tosyl chloride was carried out under standard conditions.
(
0
Table 2. Substrate scopea, b
the loading of 2a to 1.5 equiv. gave a relatively lower yield of the
product 3a (Table 1, entry 8). The decrease of the temperature
o
found that the reaction at 80 C gave the best result (Table 1,
entries 6, 9-11). Performing the reaction under ultrasonic
radiation gave 3a in only 13% yield (Table 1, entry 12). No
reaction occurred in the absence of zinc powder, and the raw
material 1a was completely recovered (Table 1, entry 13).
Table 1. Optimization of reaction conditionsa
Reductant
equiv.)
2a
Conditions
Yield
(%)b
85
N.R.
N.R.
78
82
91
84
82
Entry
(
1
2
3
4
5
6
7
8
9
Fe powder(1.5)
Al powder (1.5)
Mg powder (1.5)
Mn powder (1.5)
Zn powder (1.5)
Zn powder (1)
Zn powder (0.75)
Zn powder (1)
Zn powder (1)
Zn powder (1)
Zn powder (1)
Zn powder (1)
2 (equiv.)
2 (equiv.)
2 (equiv.)
2 (equiv.)
2 (equiv.)
2 (equiv.)
2 (equiv.)
1.5(equiv.)
2 (equiv.)
2 (equiv.)
2 (equiv.)
2 (equiv.)
100 °C, 12 h
100 °C, 12 h
100 °C, 12 h
100 °C, 12 h
100 °C, 12 h
100 °C, 12 h
100 °C, 12 h
100 °C, 12 h
80 °C, 12 h
60 °C, 12 h
r.t., 24h
93(89%)
76
1
1
1
0
1
2
20%
c
ultrasonic
13%
radiation, 1 h
80 °C, 12 h
1
3
--
2 (equiv.)
0
a
o
Reaction conditions: 1a (0.3 mmol), 2a, reductant, 60-100 C, water (1.5
mL).
b
NMR yields based on 1a; isolated yield in bracket.
c
ultrasonic radiation: 28KHz, 40W
With the optimized reaction conditions in hand, the substrate
scope ing 2-sulfonylquinoline 3cof sulfonyl chlorides was first
evaluated (Table 2). Aryl sulfonyl chlorides with a series of
important functional-groups (i.e., -Me, -OMe, -F, -Cl, -Br, -NO
CN and -CF ) on benzene ring were well tolerated to produce
the desired 2-sulfonylquinolines in good to high yields (Table 2,
a – 3k). Sterically hindered 2-methylbenzenesulfonylchloride
survived well to give the correspond in good yield. Regardless of
2
,
-
3
a
Reaction conditions: 1 (0.3 mmol), 2 (0.6 mmol), Zn powder (0.3 mmol),
o
water (1.5 ml), 80 C, 12 h.
b
3
Isolated yields based on 1.

3
To verify the practicality of the present coupling reaction, a
gram scale reaction was conducted under the optimized reaction
conditions. Delightfully, the present reaction provided the 2-
tosylquinoline 3a in 85% yield (1.20 g), showing an excellent
potential application for gram scale synthesis (Scheme 2).
Acknowledgements
This work was supported by the International
Cooperation Project of Qinghai Province (2018-HZ-806),
Qinghai key laboratory of Tibetan medicine research (2017-
ZJ-Y11), Natural Science Foundation of Shandong Province
(
ZR2018MB009 and ZR2016JL012), and the National
Natural Science Foundation of China (No. 21302109 and
1302110).
2
Supplementary data
Scheme 2. Gram-scale synthesis.
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.tetlet.****
To understand the reaction mechanism of this coupling
reaction, some control experiments were conducted. No reaction
occurred between 1a and thiosulfonate (4a) under optimal
reaction conditions, ruling out the possibility of thiosulfonate
involving in this reaction system (Scheme 3 (a)). Using zinc(II)
p-toluenesulfonate (5a) instead of tosyl chloride resulted in the
total recovery of the starting material 1a, suggesting that 5a
might not be the possible reaction intermediate (Scheme 3 (b)).
Treatment of 1a with zinc bis-sulphinate (6a) in water at 80℃for
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
Coupling reaction of haloquinolines with
sulfonyl chlorides in water
Direct coupling of haloquinolines and sulfonyl chlorides Leave this area blank for abstract info.
leading to sulfonylated quinolines in water
Pengli Bao, Leilei Wang, Qishun Liu, Daoshan Yang, Hua Wang, Xiaohui Zhao, Huilan Yue,
and Wei Wei
A facile protocol for the one-pot synthesis of various sulfonylated quinolines was developed in water under base
and organic solvent-free conditions.
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


excellent regioselectivity and scale-up
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base-, extra activator- and organic solvent-
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Graphical Abstract
(
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