Selective remote esterification of 8-aminoquinoline amides via copper(ii)-catalyzed C(sp2)-O cross-coupling reaction

Article abstract of DOI:10.1039/c6ob02375d

The remote C-O coupling of quinoline amides at the C5 position has been established using cheap and readily available copper catalyst under mild conditions. The positionally selective esterification protocol afforded C-O coupling products in moderate to excellent yields. Most importantly, this method may provide a potential alternative to the existing ways to build functionalized 5-hydroxyquinoline derivatives, which are utilized as pivotal intermediates in the synthesis of drug candidates.

Full text of DOI:10.1039/c6ob02375d

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Takeharu Haino et al.
Solvent-induced emission of organogels based on tris(phenylisoxazolyl)
benzene
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Selective Remote Esterification of 8-Aminoquinoline Amides via
Copper(II)-Catalyzed C(sp2)-O Cross-Coupling Reactions
Chengcai Xia,*[a] Kai Wang,[a] Jun Xu,[b] Chao Shen,[c] Di Sun,[a] Hongshuang Li,[a] Guodong Wang,[a]
and Pengfei Zhang[b]
0Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
The remote C-O coupling of quinoline amides on the C5 position has
been well established with cheap and available copper catalyst
under mild condition. The positional selective esterification
protocol afforded the C-O coupling products in moderate to
excellent yields. Most importantly, this method may provide a
potential alternative to the existing ways to build functionalized 5-
hydroxyquinoline derivatives, which were utilized as the pivotal
intermediates in the synthesis of drug candidates.
Over the past few decades, the palladium1 rhodium2 and
ruthenium3 catalyzed C-H functionalization to construct C-carbon
bonds and C-heteroatom bonds have received great success for the
expeditious synthesis of organic molecules. In recent years, the
status of nickel4 or copper5 catalyzed C-H functionalization is rising
step by step, due to they are cheap and available.
Scheme 1. Functionalization at C5 position of quinoline amides.
antimicrobial,9 β-galactosidase,10 tautomerase inhibitors,11
metabotropic glutamate receptor (mGluR),12 TGR5 agonists,13
TRPA1 antagonists14 and ion channels15 (Figure 1). In addition,
they have also been widely investigated in the area of reversal
of multidrug resistance.16 Hence, the synthesis of 5-hydroxy-
quinoline has attracted much attention. Some protocols for
the synthesis of 5-hydroxyquinoline have been reported, such
as bucherer reaction of 5-aminoquinoline,17 skraup reaction of
3, 5-dichloroaniline,18 deprotection of triflate or tert-butyl
carbonate esters of phenol derivatives.19 Moreover, S. K.
Agarwala20 reported a method that an arene oxides are
converted to hydroxyquinoline by microsamal epoxide
hydrolase. Despite these undisputable advances, these
methods still have many deficiencies, such as tedious
treatment and low conversion. Thus, to develop a highly
efficient and practical procedure for the synthesis of 5-
hydroxy-quinoline derivatives is highly desirable.
5-hydroxy-quinoline derivative, as
a vital group of
pharmaceutical intermediate, have been constantly used in
the synthesis of substituted quinolines which have good
biologically active such as antiviral,6 antitumor,7 antifungal,8
Figure 1. Selected biologically active pharmaceuticals of 5-
Recently, the place of quinoline functionalization is rising
step by step in organic synthetic methodology. Although some
approaches for direct construction of C−C bonds and C-
heteroatom bonds at the C5 position of quinolines have been
developed (Scheme 1),21 the methodology for the C-5 selective
formation of C−O bond has never been established.22 As part
of our continuing efforts on the functionalization of
aminoquinolines,23 we developed a copper-catalyzed C-O
coupling of quinoline amides on C5 position via C-H
esterification.
hydroxy-quinolines.
a.Pharmacy College, Taishan Medical University, Tai’an 271016, China
b.College of Material, Chemistry and Chemical Engineering, Hangzhou Normal
University, Hangzhou 310036 China E-mail: chxyzpf@hotmail.com
c. College of Biology and Environmental Engineering, Zhejiang Shuren University,
Hangzhou 310015, China
†Electronic Supplementary Information (ESI) available: Detailed experimental
procedures and analytical data. CCDC 1508095 for 2c. For ESI and crystallographic
data in CIF or other electronic format see DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
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Table 1 Optimization of the conditions for C-O coupling a
Journal Name
Table 2. Substrate scope for the C-O coupling a, b
Entry
1
2
3
4
5
6
7
8
Catalyst
NiCl2
CuI
Pd(OAc)2
FeCl3
CuCl2
Cu(OTf)2
Cu(OAc)2
-
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Oxidant
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
-
PhI(TFA)2
PhI(OH)OTs
CH3CO3H
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
PhI(OAc)2
Solvent
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
MeCN
t-BuOH
DMF
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
AcOH
Yield [%][b]
34
46
trace
trace
55
63
80
0
0
71
62
trace
trace
20
35
61
trace
70
trace
78
68
73
9
10
11
12
13c
14c
15c
16d
17e
18f
19g
20h
21i
22j
a Reaction conditions: 1 (0.2 mmol), PhI(OAc)2 (1.5 eq.), Cu(OAc)2
a Reaction conditions: 1a (0.2 mmol), catalyst (10 mol%), oxidant
(10 mol%), AcOH (2.0 mL), under air, 45 oC, 5 h. b Isolated yields.
(1.5 eq.), solvent (2.0 mL), under air, 45 oC, 5 h, unless otherwise
b
noted. Isolated yields. c AcOH (10 eq.) was added. d Cu(OAc)2 (5
role in the reaction. Among the solvents such as CH3CN, t-BuOH,
and DMF were screened (entries 13-15, Table 1), but the yields
were poor than AcOH. When the catalyst loading was reduced to 5
mol%, the yield was decreased sharply to 61% (entry 16, Table 1).
Different reaction temperatures were also investigated.
mol %). e stirred at RT. f stirred at 100 oC. g Under N2. h Under O2.
i 2 h. j 8 h.
This new C-O coupling reaction was unexpectedly and
unprecedentedly found during the course of our recent research on
C-O cross coupling utilizing a bidentate system by using nickel (II)
instead of palladium (II).24 We surprisingly found that the C5-
esterification took place in the presence of NiCl2 (10 mol%),
PhI(OAc)2 (1.5 eq.) in AcOH under air for 5 h, the unexpected
product was acquired in 34% yield (entry 1, Table 1). Inspired by
this result, various catalysts such as CuI, Pd(OAc)2, FeCl3, CuCl2,
Cu(OTf)2 and Cu(OAc)2 were screened (entries 1-7, Table 1). 10
mol % Cu(OAc)2 provided product 2a in the highest yield 80% (entry
7, Table 1). In the absence of catalyst, the reaction did not proceed
at all (entry 8, Table 1). In order to improve the yield, various
oxidants, such as PhI(OAc)2, PhI(TFA)2, PhI(OH)OTs and CH3CO3H
were examined, respectively. And PhI(OAc)2 was found to be
significantly superior. Without oxidant, the yield was zero (entries
Decreasing the temperature to room temperature, the yield
decreased to trace and up the temperature to 100 °C the yield
decreased to 70% (entries 17-18, Table 1). Also, the reaction didn’t
take place under nitrogen atmosphere but could react under
oxygen atmosphere (entries 19-20, Table 1). Finally, there were no
obvious promotion with shorten the reaction time to 2 h or
prolonging the reaction time to 8 h (entries 21-22, Table 1).
According to our suitable conditions, we then explored the
substrate scope of the current reaction (Table 2). In general, many
8-aminoquinoline amides can take place C(sp2)-O
Table 3. Substrate scope for the C-O couplinga, b
9-12, Table 1). It was found that the solvent also played a crucial
a Reaction conditions: 1 (0.2 mmol), PhI(OAc)2 (1.5 eq.), Cu(OAc)2
b
(10 mol%), R1COOH (2.0 mL), under air, 45 oC, 5 h. Isolated
Figure 2. Single-crystal X-ray structure of 2c. Ellipsoids are
represented at 30% probability
yields.
2 | J. Name., 2012, 00, 1-3
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Scheme 2. The exploration of the analogous substrates
coupling reactions, and affording the corresponding products in
moderate to good yields. Relatively speaking, electron-donating
groups such as 2-methyl, 3-methyl, 4-methyl on benzamide group
of quinoline amides which have good yields (Table 2, 2a, 2b, 2c, 2d).
In addition, the structure of the product (2c) was confirmed by X-
ray crystallography (Figure 2). Similarly, functional groups such as
fluoride, bromide also have good reactivity. Generally, either
aliphatic amides or alicyclic amides were good reaction substrates,
but they showed worse reactivity than aromatic amides to give
lower yields (Table 2, 2g, 2h, 2i, 2j, 2k). Additionally, heterocyclic
derivative of benzamide group also have a lower yield. For example,
the yield of 2l was 61% and 2m was not formed. As the former, 4-
cyanobenzoyl, 2-nitrobenzoyl with strong electron-withdrawing
group afforded a lower yield or no reaction (Table 2, 2n, 2o). Also,
many N-acyl-8-aminoquinoline derivatives have are good yields for
this reaction (Table 2, 2p, 2q).
Scheme 4. Proposed mechanism
Subsequently, we want to gain insight into the reaction
mechanism, a number of experiments were carried out (Scheme 3).
We found that the reaction were inhibited when some radical
scavengers such as BHT (butylated hydroxytoluene) or TEMPO
(2,2,6,6-tetramethyl-1-piperidinyloxy) were added in this reaction.
Furthermore, the 2,2-diphenylvinyl acetate 6 was observed when
1,1-diphenylethylene was employed as radical scavengers.
Meanwhile, the intermolecular kinetic isotope effect (KIE) has been
performed. And a low result (k = 1.0) was obtained, implying that
the C-H bond breakage was not the rate-limiting step.25
Based on the previous reports23a,23f and our observations
disclosed above, we proposed that the mechanism of this reaction
is a single electron transfer (SET) (Scheme 4). First, Cu(OAc)2 reacts
with aminoquinoline amides 1 to form a chelated intermediate (A).
Subsequently, the acyloxy radical is generated by oxidation of
PhI(OAc)2, and reacts with intermediate (A) to produce
intermediate (B). Third, a single electron transfer (SET) process
occur to generate the complex (C). Then, the reacts between of
complex (C) and Cu(OAc)2 might happen to produce intermediate (D)
and release one molecular CuOAc. Meanwhile, the Cu(OAc)2 was
reborn by oxidation. Next afford the intermediate (E) by proton
transfer (PT) process. In the end, the intermediate (E) provided the
product 2 and regenerated the Cu(OAc)2 to finish the catalytic cycle.
We have developed an regioselective C(sp2)-H esterification of
quinolines amide using Cu(OAc)2 as catalyst. This C-O coupling
revealed high efficiency and well-tolerated functionalization.
Furthermore, control experiments suggested that a single electron
transfer (SET) mechanism was involved. Finally, this method may
provide an efficient synthetic pathway to build functionalized 5-
hydroxyquinoline derivatives, which were utilized as the pivotal
intermediates in the synthesis of drug candidates.
From screened results of solvents, we could know that the
acetoxy group maybe came from AcOH. Fortunately, we use the
CD3CO2D instead of AcOH as solvent in this reaction and 2r was
obtained (Table 3). After this, many liquid acids have been
investigated and target products were obtained with good yields. It
was disappointing that we did not obtain corresponding
compounds when use other liquid acid such as butyric acid,
chloroacetic acid and trifluoroacetate. Furthermore, we attempt to
employ many solid aromatic acids in different solvents such as
DMSO, dioxane, t-BuOH, acetonitrile and other reaction conditions
are identical but yields are naught.
Many analogous substrates of 8-aminoquinoline amides were
investigated under the standard conditions (Scheme 2). And no
related acetoxylation compounds were detected. Based on these
results, we knew that 8-aminoquinoline unit was very important for
the reaction and a free NH was necessary.
This work was supported by the Zhejiang Provincial Natural
Science Foundation of China (No. LZ13B020001) and Projects
of Medical and Health Technology Development Program in
Shandong Province (No. 2015WS0102).
Notes and references
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