A facile one-pot synthesis of 2-o-cyanoaryl oxazole derivatives mediated by CuCN

Article abstract of DOI:10.1016/j.tetlet.2018.02.058

A convenient, inexpensive and effective approach to the synthesis of 2-o-cyanoaryl oxazole derivatives has been developed. Generally, the copper-mediated cyclization/coupling reactions afforded corresponding 2-cyanoaryl oxazoles and oxazolines in moderate

Full text of DOI:10.1016/j.tetlet.2018.02.058

Accepted Manuscript
A facile one-pot synthesis of 2-o-cyanoaryl oxazole derivatives mediated by
CuCN
Senbao Fan, Tao Tong, Liting Fang, Jingyi Wu, Erfei Li, Honglan Kang, Xiaoxia
Wang, Xin Lv
PII:
S0040-4039(18)30258-2
https://doi.org/10.1016/j.tetlet.2018.02.058
TETL 49743
DOI:
Reference:
Tetrahedron Letters
To appear in:
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Revised Date:
Accepted Date:
16 January 2018
20 February 2018
23 February 2018
Please cite this article as: Fan, S., Tong, T., Fang, L., Wu, J., Li, E., Kang, H., Wang, X., Lv, X., A facile one-pot
synthesis of 2-o-cyanoaryl oxazole derivatives mediated by CuCN, Tetrahedron Letters (2018), doi: https://doi.org/
10.1016/j.tetlet.2018.02.058
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A facile one-pot synthesis of 2-o-cyanoaryl
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oxazole derivatives mediated by CuCN
Senbao Fan, Tao Tong, Liting Fang, Jingyi Wu, Erfei Li, Honglan Kang, Xiaoxia Wang* and Xin Lv *

1
Tetrahedron Letters
A facile one-pot synthesis of 2-o-cyanoaryl oxazole derivatives mediated by CuCN
Senbao Fan,a Tao Tong,a Liting Fang,a Jingyi Wu,a Erfei Li,a Honglan Kang,a Xiaoxia Wanga,b,* and Xin
Lva, *
aDepartment of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People’s Republic of China.
Email: lvxin@zjnu.cn; wangxiaoxia@zjnu.cn.
bSchool of Environment and Civil Engineering, Dongguan University of Technology, Dongguan, 523808, People’s Republic of China.
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
A convenient, inexpensive and effective approach to the synthesis of 2-o-cyanoaryl oxazole
derivatives has been developed. Generally, the copper-mediated cyclization/coupling reactions
afforded corresponding 2-cyanoaryl oxazoles and oxazolines in moderate to excellent yields.
The functionalized oxazole derivatives may be useful in biological chemistry and medicinal
science. Our investigation indicates that the formation of the oxazole ring might favor the C-C
bond forming process on the ortho-position of the aryl ring. And CuCN plays dual roles as a
Lewis acid catalyst and a C-nucleophile in this transformation.
Available online
Keywords:
One-pot;
2-Cyanoaryl oxazole;
Copper;
2009 Elsevier Ltd. All rights reserved.
Cyclization;
Coupling
Substituted oxazoles are found in many natural products and
synthetic drugs exhibiting important biological activities.1 They
are also applied as intermediates2 in organic synthesis. And 2-
aryl substituted oxazoles and oxazolines are important
heterocycles because of their bioactivities and physical
properties.1b,3 Among these heterocyclic molecules, 2-cyanoaryl
oxazole derivatives were reported as useful molecules in
biological chemistry and medicinal science. For example, a 2-o-
cyanoaryl oxazole derivative (Figure 1, A) can be utilized for
treating PPAR related diabetes, dyslipidemia, obesity and
inflammatory disorders;4 an N-cyanomethylcyclohexane-
carboxamide containing 2-cyanoaryl oxazole moiety (B) was
studied as a cathepsin cysteine protease inhibitor;5 2-o-
cyanophenyl oxazole (C) might possess antiprotozoal activity;6
and certain oxazoles bearing cyanoaryl substituent such as (D)
were evaluated to have potential activity against eIF4A3.7
The typical methods utilized to build the 2-aryl oxazole motif
include the condensation between -hydroxynitriles and
benzaldehydes (Fischer oxazole synthesis),8 the arylation of
oxazoles9 or 2-halo oxazoles,10 the cylization of N-
propargylbenzamides,11 etc.1b,12 Although there are numerous
synthetic routes to the assembly of 2-aryl oxazoles, there still
remains a need for more convenient and efficient approaches that
afford 2-o-cyanoaryl oxazoles in one pot.
Copper-mediated domino reactions has recently aroused
increasing interest since they provide facile and efficient
approaches to the one-pot construct of structurally diversified
molecules.13 Our group are interested in developing copper-
mediated one-pot reactions for the convenient assembly of
various heterocycles.14 Herein, we report a facile one-pot
synthesis of 2-o-cyanoaryl oxazole derivatives from the domino
reactions of o-bromo N-propargylbenzamides mediated by
CuCN.
At the outset of our studies, the reaction of o-bromo N-
propargylbenzamide 1a with CuCN was chosen as the model
reaction to study the feasibility of this one-pot synthesis (Table
1, entry 1). A moderate yield of the expected o-cyano-modified
2-phenyl oxazole 2a was delivered when the substrate 1a reacted
with CuCN in the presence of diisopropylethylamine (DIPEA, 2
equiv) in refluxing dioxane (entry 1). Under these conditions, a
small amount (23%) of by-product 3a generated from the simple
cyclization of 1a was isolated. Two common ligands (L-proline
and 1,10-phen) were tested for this copper-mediated one-pot
transformation in order to enhance the efficiency of the coupling
process. However, the results were unsatisfying in both cases
(entries 2 and 3). Then a variety of bases were evaluated. The
Figure 1. Some biologically active 2-o-cyanoaryl oxazole derivatives.

2
Tetrahedron
investigation indicated that the bases have significant effect on
desired product 2a could be improved slightly when the mixture
was stirred at 115 °C (entry 18). However, the result was
deteriorated when the reaction was performed at 120 °C (entry
19), probably because the rate of hydrolysis of the amide-type
substrate increased at a higher temperature under the basic
conditions. All of the trials afforded the cyclized product with
excellent regioselectivity and 5-exo-dig cyclization was
exclusively observed in each case.
the reaction efficacy (entries 4-11). TEA and DMAP showed
slightly less effective than DIPEA, and the use of TMEDA,
DABCO, DBU and inorganic bases (such as K2CO3 and Cs2CO3)
were ineffective for this transformation. Gratifyingly, the
reaction worked better when TMPEA was employed (entry 9).
Different solvents were also studied for this transformation
(entries 9 and 12-17). And DMAc was proven to be the optimal
solvent for the one-pot reaction (entry 14). The yield of the
Table 1. Optimization of the reaction conditionsa
Entry
Solvent
Base
Ligand
Yield of 2ab
Yield of 3ab
Temp. (°C)
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
dioxane
dioxane
dioxane
dioxane
dioxane
dioxane
dioxane
dioxane
dioxane
dioxane
dioxane
toluene
DIPEAc
DIPEA
DIPEA
TEA
-
101
101
101
101
101
101
101
101
101
101
101
105
110
110
110
110
110
115
120
45%
32%
nd
38%
trace
trace
trace
34%
56%
nd
23%
18%
trace
34%
nd
51%
45%
40%
16%
trace
nd
32%
18%
12%
nd
21%
20%
7%
L-prolined
1,10-phend
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
TMEDAe
DABCO
DBU
DMAP
TMPEAf
K2CO3
Cs2CO3
TMPEA
TMPEA
TMPEA
TMPEA
TMPEA
TMPEA
TMPEA
TMPEA
nd
trace
61%
70%
trace
49%
46%
75%
62%
DMF
DMAc
DMSO
NMP
2-methoxy ethanol
DMAc
DMAc
trace
a Reaction conditions: unless otherwise noted, the reaction was carried out with substrate 1a (0.5 mmol), CuCN (0.65 mmol, 1.3 equiv.),
base (2.0 mmol, 4.5 equiv.), in solvent (2 mL) at indicated temperature for 24 h.
b Isolated yield.
c DIPEA = Diisopropylethylamine.
d Ligand (20 mol%) was added.
e TMEDA = Tetramethylethylenediamine.
f TMPEA = Tetramethylpropylenediamine.
Having established the optimal reaction conditions for the
copper-mediated cycloisomerization/coupling, the scope and
generality of this method were subsequently investigated. As
summarized in Table 2, the one-pot transformation showed broad
substrate scope and furnished the corresponding 2-o-cyanoaryl
oxazoles 2 in moderate to excellent yields.15 First, several
substrates with different substituents on the o-bromophenyl ring
were employed (the synthesis of 2a-2d). The reaction proceeded
smoothly when the substrates have either electron-withdrawing
group (p-Cl, p-CF3) or electron-donating group (p-OMe) on the
aromatic ring. Variation of the substituents at the -position of
the N-propargyl group was also feasible (the synthesis of 2e-2u).
A variety of alkyl groups such as benzyl (2e-2f), phenethyl (2g-
2i), phenylpropyl (2j-2k) were well tolerated. The reactions of
substrates bearing long linear or branched groups also afforded
the corresponding substituted oxazoles in moderate yields (the
synthesis of 2l-2m). Interestingly, the substrates with -
disubstituted N-propargyl groups reacted more effectively and
gave excellent yields of the desired 2-o-cyanoaryl oxazolines (the
synthesis of 2n-2t). Notably, several spirocyclic oxazoline
derivatives were efficiently assembled when o-bromo N-(1-
ethynylcyclohexyl)benzamides were utilized as the substrates
(the synthesis of 2q-2t). A relatively lower yield was obtained
when the phenyl was introduced onto -position of the N-
propargyl group (the synthesis of 2u). The reaction of a piperinic
acid-derived substrate also proceeded successfully and the
corresponding heterocyclic derivative was constructed in a
moderate yield (the synthesis of 2v). When a substrate with an
α,γ-disubstituted N-propargyl group was applied, the desired
oxazoline product could also be generated, despite the relatively
lower the yield (the synthesis of 2w).
We then attempted to apply our method to the synthesis of m-
cyanoaryl and p-cyanoaryl oxazoles. To our surprise, only
moderate yields of the by-products (3h and 3g) generated from
the simple cyclization were detected in company with trace
amounts of final products 2 in both cases (Scheme 1, eq. 1 and eq

3
Table 2. CuCN-mediated one-pot synthesis of various 2-o-cyanoaryl oxazole derivativesa,b
a Reaction conditions: unless otherwise noted, the reaction was carried out with substrate 1 (0.5 mmol), CuCN (0.65 mmol, 1.3 equiv.),
TMPEA (2.0 mmol, 4.5 equiv.), in DMAc (2 mL) at 115 °C for 24 h.
b
Isolated yields of product 2 were reported. In some cases, by-product 3 generated from the simple cyclization of 1 was also isolated
and the yields were given in parentheses.
c At 120 °C.
2). Almost no cyanated products were detected when the isolated
2-m- and 2-p-bromophenyl oxazoles 3h and 3i were subjected to
the reactions under the CuCN-mediated conditions respectively
(eq. 3 and eq. 4). However, the reaction of intermediate 3a
afforded the corresponding o-cyanophenyl oxazole 2a in a good
yield under the same conditions. These results indicate that the
oxazole moiety at the ortho-position of the phenyl ring might
facilitate the cyanation process.
In order to further probe the pathway of the one-pot synthesis
of 2-o-cyanophenyl oxazoles, two additional control experiments
were also performed as shown in Scheme 2. A 63% yield of
product 3a derived from the simple cycloisomerization was

4
Tetrahedron
and o-bromoaryl ring of IV to form Cu(I) complex V. V
underwent an oxidative addition/reductive elimination process to
provide the final 2-o-cyanophenyl oxazole 2 along with the
regenerated Cu(I) species. It is worth noting that the coordination
between the copper(I) species and the oxazole ring might
stabilize the intermediates and facilitate the C-C bond formation
on the ortho-position of the phenyl ring.
Scheme 3. A plausible pathway for the CuCN-mediated one-
pot synthesis of 2-o-cyanoaryl oxazole
Scheme 1. The reactions of m-bromo and p-bromo substrates
In conclusion, we have developed a facile and efficient one-
pot synthesis of 2-o-cyanoaryl oxazole derivatives. Mediated by
CuCN/TMPEA,
a
variety of substituted 2-o-cyanoaryl
oxazole/oxazolines could be assembled in moderate to excellent
yields from o-bromo N-propargylbenzamides and CuCN through
a cyclization/coupling process. Various substituents were well
tolerated under these conditions. In this transformation, CuCN
plays dual roles as a Lewis acid catalyst and a cyanide anion
source. Moreover, our studies found that the formation of the
oxazole moiety might favor the subsequent intermolecular
coupling process.18 The convenient procedures, easily accessible
starting materials and good efficiency would make the protocol
useful for the synthesis of related heterocyclic molecules with
interesting biological activities.
Acknowledgments
Scheme 2. Two additional control experiments
We are grateful to the Natural Science Foundation of Zhejiang
Province (No. LY16B020003 and LY14B020001) for financial
support.
isolated in company with trace amount of 2a after the mixture
was stirred at 100 °C (eq. 1). When the reaction was performed at
110 °C for 24 h, the desired product 3a was isolated in 70% yield
with small amount of 2a (eq. 2), indicating that 3a was an
intermediate that could be converted into the final product under
these conditions. However, when the reaction time was
prolonged to 48 h, a slightly higher yield of 2a was obtained in
company with 7% yield of 3a (eq. 3).16
References and notes
1.
For selected reviews, see: (a) Yeh, V. S. C. Tetrahedron 2004; 60:
11995− 12042. (b) Turchi, I. J.; Dewar M. J. S. Chem. Rev. 1975;
75:389–437.
On the basis of the experimental observations and the related
reports,11,17 a plausible pathway for the one-pot transformation is
depicted in Scheme 3. Copper(I)-ligand species (ligand =
TMPEA) coordinated with the alkynyl group of substrate 1 to
afford Cu(I) complex I (the alkyne was electrophilically
activated). Then the regioselective 5-exo-dig-type intramolecular
cyclization followed by protonolysis gave the corresponding
oxazoline-type intermediate III, which was subsequently
converted into oxazole-type intermediate IV via an isomerization
process. CuCN-ligand species coordinated with the oxazole ring
2.
3.
4.
Wasserman, H. H.; McCarthy, K. E.; Prowse, K. S. Chem. Rev.
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A selected review: Zificsak, C. A.; Hlasta, D. J. Tetrahedron
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(a) Su W. G. US patent 20050187266, 2005; Chem. Abstr. 143:
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5
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(a) Brooks, D. A. Fischer Oxazole Synthesis In Name Reactions in
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Z.-K.; Hu, T.-T.; Shao, L.-X. Org. Lett. 2014; 16:1984–1987. (b)
Yu, X. Z.; Li, X. W.; Wan, B. S. Org. Biomol. Chem. 2012;
10:7479–7482. (c) Yang, F. Z.; Xu, Z. Q.; Wang, Z.; Yu, Z. K.;
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T. T.; Wang, X. X.; Lv, X. Tetrahedron Lett. 2015; 56:1624–
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Wang, X. X.; Lv, X. J. Org. Chem. 2014; 79:9000–9008. (f) Yuan,
G. D.; Liu, H. Q.; Gao, J. L.; Xu, H. J.; Jiang, L.; Wang, X. X.; Lv,
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Chen, L. B.; Shao, Y. Y.; Zhu, J. Q.; Huang, Y. J.; Wang, X. X.;
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Lv, X. Adv. Synth. Catal. 2013; 355:1185–1192.
9.
15. General procedure for the Cu-mediated one-pot synthesis of 2-o-
cyanoaryl oxazoles: An oven-dried Schlenk tube was charged with
a magnetic stir bar, substrate 1 (0.5 mmol, 1.0 equiv), CuCN (0.65
mmol, 1.3 equiv), The tube was capped, and then evacuated and
backfilled with nitrogen (3 times). TMPEA (2.25 mmol, 4.5
equiv) in DMAc (1.5 mL) was added via syringe under nitrogen at
room temperature. Then the mixture was stirred at 120 °C for 24 h
(monitored by TLC). The mixture was cooled to room
temperature, diluted with water (15 mL), and extracted with
EtOAc (20 mL). The aqueous layer was extracted with EtOAc (3
× 20 mL). The combined organic layers were washed with brine,
and dried over Na2SO4. After filtration and removal of the solvent
in vacuo, the residue was purified by column chromatography on
silica gel using petrol/AcOEt as eluent to give the product.
16. The yield increased rather slightly when the reaction time was
extended to 48 h, probably because that small amount of the
substrate was inevitably decomposed during the initial process,
and the reaction rate decreased when the concentration of cyanide
ion was lowered.
17. (a) Cristau, H.-J.; Ouali, A.; Spindler, J.-F.; Taillefer, M. Chem.
Eur. J. 2005; 11:2483–2492. (b) Zanon, J.; Klapars, A.; Buchwald,
S. L. J. Am. Chem. Soc. 2003; 125:2890–2891.
18. This is the first example that systematically studies the copper-
mediated intermolecular cyanation of aryl bromides assisted by an
o-oxazolyl group, which is constructed in situ. It was observed
that there was certain connection between the two different
processes and the effective combination of the two protocols
(cyclization and coupling) would give an alternative and
convenient access to a variety of 2-o-cyanoaryl oxazole
10. For selected examples, see: (a) Senger, J.; Melesina, J.; Marek, M.;
Romier, C.; Oehme, I.; Witt, O.; Sippl, W.; Jung, M. J. Med.
Chem. 2016; 59:1545–1555. (b) Haemmerle, J.; Spina, M.;
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2008:3099–3107.
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Su, J. H.; Du, J. F.; Song, W. L. Chem. Commun. 2017; 53:10366–
10369 (under Au catalysis). (b) Alhalib, A.; Moran, W. J. Org
Biomol Chem. 2014; 12:795–800. (c) Senadi, G. C.; Hu, W.-P.;
Hsiao, J.-S.; Vandavasi, J. K.; Chen, C. Y.; Wang, J. J. Org Lett.
2012; 14:4478–4481. (d) Egorova, O. A.; Seo, H.; Kim, Y.; Moon,
D.; Rhee, Y. M.; Ahn, K. H. Angew. Chem. Int. Ed. 2011;
50:11446–11450. (e) Jin, C.; Burgess, J. P.; Kepler, J. A.; Cook, C.
E. Org Lett. 2007; 9:1887–1890. (f) Hashmi, A. S. K.; Weyrauch,
J. P.; Frey, W.; Bats, J. W. Org Lett. 2004; 6:4391–4394.
12. The Robinson-Gabriel oxazole synthesis: (a) Palmer, D. C.;
Venkatraman, S. In Oxazoles: Synthesis, Reactivity and
Spectroscopy. Part A; Palmer, D. C., Ed.; John Wiley & Sons Inc.:
Hoboken, NJ, 2003. (b) Robinson, R. J. Chem. Soc.
1909;95:2167–2168. The oxidative annulation of carbonyl
compounds with amines: (a) Gao, Q.-H.; Fei, Z.; Zhu, Y.-P.; Lian,
M.; Jia, F.-C.; Liu, M.-C.; She, N.-F.; Wu, A.-X. Tetrahedron
2013; 69:22–28. (b) Xu, Z. J.; Zhang, C.; Jiao, N. Angew. Chem.
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3870.
derivatives. Till now, although many studies on o-oxazoline-
assisted C-X bond functionalization of aryl halides have been
reported, there is only one paper described the CuCN-mediated
synthesis of 2-o-cyanoaryl oxazole derivatives from o-haloaryl
oxazoles: Clark, R. L.; Pessolano, A. A.; Witzel, B.; Lanza, T.;
Shen, T. Y. J. Med. Chem. 1978; 21:1158-1162. The application
scope was rather narrow (the related substrates were limited to o-
halophenyl 2-oxazolo[4,5-b]pyridines), and the ortho effect of the
oxazolyl group was not mentioned.
13. For important reviews, see: (a) Liu, Y.; Wan J. Chem. Asian J.
2012; 7:1488–1501. (b) Liu, Y.; Wan, J. Org. Biomol. Chem.
2011; 9:6873–6894.
14. (a) Mao, X.; Tong, T.; Fan, S. B.; Fang, L. T.; Wu, J. Y.; Wang, X.
X.; Kang, H. L.; Lv, X. Chem. Commun. 2017; 53:4718–4721. (b)
Xu, B. Q.; Peng, B.; Cai, B. L.; Wang, S. S.; Wang, X. X.; Lv, X.
Adv. Synth. Catal. 2016; 358:653–660; (c) Tang, J. M.; Xu, B. Q.;
Mao, X.; Yang, H. Y.; Wang, X. X.; Lv, X. J. Org. Chem. 2015;

6
Tetrahedron
Highlights
▪ It provides a convenient and efficient access to 2-
o-cyanoaryl oxazole derivatives.
▪ Various substituents are well tolerated under these
conditions.
▪ The formation of oxazole ring at the ortho-
position favors the cyanation process.
▪ CuCN plays dual roles as a Lewis acid catalyst
and a cyanide anion source.

7
Graphical Abstract
A facile one-pot synthesis of 2-o-
cyanoaryl oxazole derivatives mediated
by CuCN
Senbao Fan,a Tao Tong,a Liting Fang,a Jingyi Wu,a
Erfei Li,a Honglan Kang,a Xiaoxia Wanga,b,* and
Xin Lva, *
aDepartment of Chemistry, College of Chemistry and Life Sciences,
Zhejiang Normal University, Jinhua 321004, People’s Republic of
China. Email: lvxin@zjnu.cn; wangxiaoxia@zjnu.cn.
bSchool of Environment and Civil Engineering, Dongguan University
of Technology, Dongguan, 523808, People’s Republic of China.