Synthesis of 3,3-Disubstituted Oxindoles Containing a 3-(4-Aminobut-2-ynyl) Unit via Domino Heck-Sonogashira Reaction in Water

Article abstract of DOI:10.1002/adsc.201500887

In this study, palladium-catalyzed domino Heck-Sonogashira reactions have been developed in water. Using this strategy, a series of 3-(4-aminobut-2-ynyl)oxindole derivatives with an all-carbon quaternary center at the 3-position were easily synthesized. The reactions provided products in excellent yields with a broad substrate tolerance. The target product was readily converted into a pharmaceutically active molecule, which is used as a 5-HT₇ receptor antagonist.

Full text of DOI:10.1002/adsc.201500887

UPDATES
DOI: 10.1002/adsc.201500887
Very Important Publication
Synthesis of 3,3-Disubstituted Oxindoles Containing a
3
-(4-Aminobut-2-ynyl) Unit via Domino Heck–Sonogashira
Reaction in Water
a,b
b
b
b
Dong-Chao Wang, Hai-Xia Wang, Er-Jun Hao, Xiao-Han Jiang,
b
a,b,
a,b,
Ming-Sheng Xie, Gui-Rong Qu, * and Hai-Ming Guo *
a
School of Environment, Henan Normal University, Xinxiang, Henan Province 453007, Peopleꢀs Republic of China
School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions of Ministry of
Education, Henan Normal University, 46 Jianshe Road, Xinxiang 453007, Peopleꢀs Republic of China
Fax: (+86)-373-332-9276; e-mail: quguir@sina.com or guohm518@hotmail.com
b
Received: September 22, 2015; Revised: December 9, 2015; Published online: January 18, 2016
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201500887.
Abstract: In this study, palladium-catalyzed domino
Heck–Sonogashira reactions have been developed
in water. Using this strategy, a series of 3-(4-amino-
but-2-ynyl)oxindole derivatives with an all-carbon
quaternary center at the 3-position were easily syn-
thesized. The reactions provided products in excel-
lent yields with a broad substrate tolerance. The
target product was readily converted into a pharma-
ceutically active molecule, which is used as a 5-HT7
receptor antagonist.
As a powerful method for constructing complex or-
ganic molecules, domino reactions for the one-step
formation of two or more bonds under identical reac-
tion conditions have been extensively employed by
[5]
synthetic chemists. Domino Heck reactions using
a Heck reaction as an initiation reaction have been
explored in the literature and are becoming a focus
[6]
for researchers. Several domino Heck reactions,
[
6a,7]
[8]
such as Heck–Suzuki,
reductive Heck, Heck-CÀ
[9]
[6b]
H activation,[ Heck-carbohalogenation, and Heck-
10]
aza-Michael,
have been reported, and some of
[11]
them have been employed for the total synthesis of
natural products and their analogs. Most recently, our
Keywords: domino reaction; Heck reaction; oxin-
doles; Sonogashira reaction; terminal alkynes;
water
The 3,3-disubstituted oxindole framework is a key
structural unit found in various natural products and
[
1]
[2a]
drugs. As shown in Figure 1, amedalin
(1) is an
antidepressant drug, which was synthesized in the
[
2b]
early 1970s, isapheninum (2) is a laxative used for
several years as a non-prescription drug before it was
[
2c]
taken off the market in 1972, and linopiridine (3) is
in Phase III clinical trials for the treatment of Alz-
heimerꢀs disease. Recently, a series of new oxindole
compounds exhibiting pharmaceutical activity has
[
3]
been reported.
(Phenylpiperazinylbutyl)oxindoles
(
4, Figure 1) are selective 5-HT receptor antagonists,
7
and (phenylpiperidinylbutyl)oxindoles (5) can be used
as neurokinin receptor antagonists. Thus, the 3,3-di-
substituted oxindole framework is commercially im-
portant; hence, it is imperative for organic chemists
to develop new synthetic procedures for obtaining
[
4]
these sub-units.
Figure 1. Pharmaceutically active compounds and drugs con-
taining 3,3-disubstituted oxindole units.
4
94
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2016, 358, 494 – 499

UPDATES
Synthesis of 3,3-Disubstituted Oxindoles Containing a 3-(4-Aminobut-2-ynyl) Unit
[
12]
group
has reported the first example of a three- Table 1. Optimization of the domino Heck–Sonogashira re-
[
a]
action conditions.
component domino Heck–Negishi coupling reaction
for synthesizing novel purine compounds. The domino
Heck reaction of 2-haloaniline derivatives is a very
direct, effective method for synthesizing oxindoles.
[
7a]
[6a]
Grigg and Somfai have employed domino Heck–
Suzuki coupling reactions for synthesizing 3,3-disub-
[13]
stituted oxindoles. In 2007, Zhu and co-workers
have developed a domino Heck-cyanation process for
obtaining 3,3-disubstituted oxindoles with the CN
[
14a]
group. Balalaie
has reported a domino carbopalla-
dation-Sonogashira reaction of N-(2-halophenyl)pro-
Entry Cat.
x
Base
Temp.
8C]
Yield
[%]
piolamide compounds for synthesizing 3-arylideneox-
[b]
[
[
14b]
indoles. Li
has developed a domino Heck–Sonoga-
1
2
3
4
5
6
7
8
9
PdCl2
10 Et N
10 Et N
10 Et N
10 Et N
60
60
60
60
60
60
60
49
57
80
32
75
95
40
88
88
65
50
65
39
96
96
94
96
95
90
shira palladium-catalyzed process in the presence of
a copper(I) co-catalyst. Recently, the development of
new synthetic methods with a low environmental
impact is one of the most important branches of
3
Pd(OAc)2
3
Pd(PPh3)4
PdCl ·dppf
PdCl ·(PPh ) 10 Et N
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
3
2
3
[
15]
2
3
2
3
modern synthetic chemistry.
Thus, the reactions
10 DBU
10 pyridine
10 pyrrolidine 60
10 piperidine 60
10 DABCO
10 K CO
10 DBU
10 DBU
10 DBU
10 DBU
10 DBU
5
2
1
using water as the medium have attracted significant
attention, and many organic reactions in water have
[
16]
[15,17]
been reported by our group and other
groups.
Herein, we report an efficient synthesis of new 3- 10
alkyl-3-(4-aminobut-2-ynyl)-substituted oxindole com- 11
60
60
40
r.t.
70
90
100
90
90
90
Pd(PPh
)
3
4
4
4
2
3
1
1
1
1
1
1
1
1
2
3
4
5
6
7
8
9
Pd(PPh3)
pounds by a domino Heck–Sonogashira sequence pal-
ladium-catalyzed process in water. The most impor-
tant aspect of this sequence is to easily construct the
structural framework of 3,3-disubstituted oxindoles 4
and 5.
Initially, N-(2-iodophenyl)methacrylamide (6a) and
N-methyl-N-propargylaniline (7a) were selected as
model substrates for optimizing the reaction condi-
Pd(PPh3)
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
DBU
DBU
DBU
[
a]
Reaction conditions: 6a (0.1 mmol), 7a (0.2 mmol), base
0.3 mmol), N , stirring for 15 h at the corresponding
tions (Table 1). When PdCl was used as the catalyst,
2
(
2
the reaction proceeded well in the presence of Et N,
3
temperature shown in the table.
Isolated yields of products are given based on 6a.
and the desired domino product 8aa was isolated in
[b]
4
9% yield (entry 1). A different palladium source can
affect the reaction outcome: higher yields were ob-
tained when Pd(PPh ) was employed (entry 3). Sub- process under the optimized conditions. Scheme 1
3
4
sequently, several bases were examined, and 1,8-di- shows the effect of the haloaniline subunit on the re-
azabicyclo[5.4.0]undec-7-ene (DBU) provided the de- action outcome. N-(2-Bromophenyl)methacrylamide
sired product in 95% yield (entry 6). The reaction was (6b) afforded the target products 8aa in 59% yield,
clearly affected by temperature. Poor yields were ob- while N-(2-chlorophenyl)methacrylamide (6c) failed
tained at lower temperature (entry 13), yet similar to produce 3,3-disubstituted oxindoles. On the other
yields were obtained above 608C, but the yield of the hand, the iodine-substituted aniline provided the
product decreased at 1008C (entry 16). Finally, product in 95% yield; hence, iodine is selected as the
a series of experiments was conducted for determin- best leaving group for the following investigation. As
ing the lowest effective amount of Pd(PPh ) , which shown in Scheme 2, a comparison experiment was
3
4
was determined to be 2 mol%; this reaction provided conducted to investigate the effect of the substitution
nearly the same yield as a reaction with 10 mol% of the amide nitrogen atom. N-Methylamide 6d
Pd(PPh ) (entries 17–19). Thus, the optimized reac- smoothly gave the 3,3-disubstituted oxindole 8da in
3
4
tion conditions are as follows: 2 mol% of Pd(PPh ) , 94% yield. The unprotected amide 6e afforded
3
4
[9b,14b]
0
2
3
.1 mmol of N-(2-iodophenyl)methacrylamide (6a), a result similar to that in a previous study
and
.0 equiv. of N-methyl-N-propargylaniline (7a), and failed to produce the target products 8ea. However,
.0 equiv. of DBU in 0.5 mL of water at 908C the desired product 8fa was not obtained when N-
(
entry 18).
Boc-amide 6f was used. 2-Iodoaniline derivatives 6g–j
Subsequently, a range of substituted aniline deriva- with electron-donating or electron-withdrawing
tives was employed in the domino Heck–Sonogashira groups were well tolerated and afforded the desired
Adv. Synth. Catal. 2016, 358, 494 – 499
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
495

Dong-Chao Wang et al.
UPDATES
Scheme 1. Effect of the haloaniline subunit on the reaction outcome. Reaction conditions: 6 (0.1 mmol), 7a (2.0 equiv.), DBU
(
3.0 equiv.), Pd(PPh ) (2 mol%), H O (0.5 mL), 908C, N , stirring overnight. Isolated yields of products are given based on
3 4 2 2
6.
Scheme 2. Reaction of various substituted aniline deriva-
tives. Reaction conditions: 6 (0.1 mmol), 7a (2.0 equiv.),
DBU (3.0 equiv.), Pd(PPh ) (2 mol%), H O (0.5 mL), 908C,
3
4
2
N , stirring overnight. Isolated yields of products are given
2
based on 6.
domino products in good yields (8ga–8ja). Subse-
quently, variation of the substituent on the acrylamide
was evaluated; the desired domino reaction of 2-
propyl-, 2-benzyl- and 2-phenylacrylamides (6k, 6l,
6
m) smoothly proceeded and afforded the corre-
sponding 3,3-disubstituted oxindole compounds in
good yields (8ka–8ma).
Next, various propargylamine-bearing compounds
were examined for determining the scope of the
domino reaction. From the experimental results
shown in Scheme 3, the substituents of the propargyl-
amine nitrogen atom marginally affect the domino
Heck–Sonogashira process. Unprotected amine 7b
and the acetyl-protected amine 7c afforded the de-
Scheme 3. Reaction of various alkyne derivatives. Reaction
conditions: 6a (0.1 mmol), 7 (2.0 equiv.), DBU (3.0 equiv.),
sired products in 94% and 95% yield, respectively Pd(PPh ) (2 mol%), H O (0.5 mL), 908C, N , stirring over-
3
4
2
2
(8ab and 8ac). Propargylamine derivatives (7d–g) night. Isolated yields of products are given based on 6a.
4
96
asc.wiley-vch.de
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2016, 358, 494 – 499

UPDATES
Synthesis of 3,3-Disubstituted Oxindoles Containing a 3-(4-Aminobut-2-ynyl) Unit
Scheme 5. Proposed mechanism of the domino Heck–Sono-
gashira reaction.
was transformed into known compound 4, which is
a selective 5-HT receptor antagonist.
7
A possible mechanism for this domino Heck–Sono-
[1b,18]
gashira process is shown in Scheme 5.
In this
mechanism, the first step involves the oxidative addi-
tion of Pd(0) to the carbon-iodine bond of acrylamide
6a to form intermediate 9. The intramolecular Heck
insertion of intermediate 9 proceeds to form a primary
alkylpalladium complex species 10. Then, one of the
Scheme 4. Synthesis of 5-HT receptor antagonists.
7
with electron-donating or electron-withdrawing ligands of the complex 10 is replaced by alkyne 7, af-
groups on the phenyl rings were well tolerated, af- fording intermediate 11. Ligated alkyne 11 is easily
fording the desired domino products in good yields dehydroiodinated in the presence of base, forming the
(8ad–8ag). Following this, the propargylamine-con- new intermediate 12. Finally, the reductive elimina-
taining chain or cyclic groups were also evaluated. tion of intermediate 12 occurs to regenerate the
The results show that all propargylamine-containing active Pd(0) species and afford the desired product 8.
chain or cyclic groups could readily afford the corre-
In summary, a mild, general domino palladium-cat-
sponding products in excellent yields (8ah–8al). For alyzed Heck–Sonogashira reaction in water was de-
developing the scope of the optimized reaction condi- veloped for the synthesis of 3-(4-aminobut-2-ynyl)ox-
tions again, other types of alkynes were employed in indole derivatives with an all-carbon quaternary
the domino processes. Ethynylbenzene 7m and 7n as center at the 3-position in excellent yields. This
well as propargyl alcohol 7o were smoothly trans- domino process can be applicable for various acryla-
formed into the desired oxindoles 8am–8ao. However, mides and terminal alkynes. This reaction is attractive
none of the desired products were obtained using because the structures of the target products are simi-
ethynyltrimethylsilane 7p and ethyl propiolate 7q lar to the molecules used as 5-HT receptor antago-
7
(8ap and 8aq).
nists and neurokinin receptor antagonists, which
The new products of the domino Heck–Sonogashira could be readily converted into the above antagonists.
reaction exhibit an all-carbon quaternary center at
the 3-position with a propargyl group. This character-
istic attracted our attention not only from a biological
viewpoint, but also as a synthetically valuable adduct.
Notably, the target products could be further convert-
Experimental Section
Typical Experimental Procedure for the Synthesis of
Oxindole Derivatives in Water
ed to molecules which can be used as 5-HT receptor
7
antagonists and neurokinin receptor antagonists. As
shown in Scheme 4, product 8nl prepared from acryl- To a Schlenk tube equipped with a magnetic stir bar, N-(2-
amide 6n and propargylpiperazine 7l in 95% yield iodophenyl)methacrylamide 6a (0.1 mmol, 37.7 mg), N-
Adv. Synth. Catal. 2016, 358, 494 – 499
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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497

Dong-Chao Wang et al.
UPDATES
methyl-N-propargylaniline 7a (0.2 mmol, 29 mg), and
Pd(PPh3)4 (2.3 mg, 2 mol%) were added. The tube was
sealed with threaded rubber stopper, evacuated and backfil-
led with N (this process was repeated for 3 times). H O
I. N. Gyoenos, K. Pallagi, M. Porcs-Makkay, G. SzØnµsi,
T. Mezel, G. Lukµcs, G. LØvay, A. Egyed, L. G.
Hµrsing, U.S. Patent Appl. US20120108607, 2012;
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Stroth, B. Volk, S. Lehel, A. Dyssegaard, A. Ettrup, P.
Svenningsson, G. M. Knudsen, J. L. Kristensen, J. Med.
Chem. 2015, 58, 3631.
2
2
(0.5 mL) and DBU (0.3 mmol, 45 mL) were then added via
syringe. The mixture was stirred at 908C until 6a had disap-
peared (monitored by TLC). The reaction mixture was ex-
tracted with ethyl acetate (10.0 mL). The organic phase was
dried over Na SO and concentrated under vacuum. The re-
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4
sulting residue was purified by flash chromatography over
silica gel (ethyl acetate/petroleum ether) to afford the de-
sired product 1-benzyl-3-methyl-3-{4-[methyl(phenyl)ami-
no]but-2-yn-1-yl}indolin-2-one (8aa) as a colorless oil; yield:
1
3
7.6 mg (95%). H NMR (CDCl , 400 MHz): d=7.26–7.30
3
(m, 7H), 7.12–7.16 (m, 2H), 6.93 (t, J=7.6 Hz, 1H), 6.84 (t,
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1
3
2
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2
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2
Acknowledgements
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We are grateful for the financial support from the National
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2
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