One-Pot Synthesis of 1-Monosubstituted 1,2,3-Triazoles from Propargyl Alcohol

Article abstract of DOI:10.1055/s-0036-1589157

A one-pot synthesis of 1-monosubstituted-1,2,3-triazoles from propargyl alcohol and various aryl azides was achieved. This simple method provides concise and efficient access to various 1-monosubstituted 1,2,3-triazole derivatives through a three-step one

Full text of DOI:10.1055/s-0036-1589157

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© Georg Thieme Verlag Stuttgart · New York
2018, 29, A–E
letter
A
de
C. Han et al.
Letter
Synlett
One-Pot Synthesis of 1-Monosubstituted 1,2,3-Triazoles from
Propargyl Alcohol
Chunmei Hana
1) CuI, NaAsc, MeCN, 80 °C, 5 h
2) KMnO4, Na2CO3, 80 °C, 8 h
N
N
Suping Donga
Wensheng Zhangb
Zhen Chen*a
R
N3
+
N
R
OH
3) Ag2O, K2S2O8, 100 °C, 24 h
NaAsc = sodium ascorbate
R = Aryl bearing Me, OMe, F, Cl, Br, SO2NH2, NO2
17 examples 70–93% yields three steps one-pot
a Faculty of Science, Kunming University of Science and Technology,
Kunming 650500, P. R. of China
b School of Science and Technology, Jiaozuo Teachers’ College, Jiaozuo
454001, P. R. of China
chenzhen69@qq.com
Received: 11.10.2017
Accepted after revision: 29.11.2017
Published online: 31.01.2018
Owing to their wide range of uses, several strategies for
the syntheses of 1,2,3-triazoles have been reported. The
first method that was used to construct the 1,2,3-triazole
ring was the Huisgen dipolar cycloaddition, which gives
1,4- and 1,5-disubstituted regioisomers without regioselec-
tivity; in this reaction, an alkyne and an azide are mixed
and heated.9 In 2002, the Sharpless group10 developed a
copper-catalyzed 1,3-dipolar cycloaddition reaction of ter-
minal alkynes and azides for the regioselective construc-
tion of 1,4-disubstituted 1,2,3-triazoles. This method is
simple and vigorous. Subsequently, these compounds came
into the limelight, attracting interested researchers who ex-
plored more-effective methods for the construction of this
type of molecule through various approaches.11 For exam-
ple, the Fokin group12 used a triazole ligand to stabilize
Cu(I), which can vigorously catalyze the Huisgen cycloaddi-
tion reaction to form 1,4-substituted 1,2,3-triazoles at
ambient temperatures. Orgueira et al.13 found that active
nanoparticulate copper also catalyzes the Huisgen cycload-
dition reaction with high efficiency in a broad range of sol-
vents, including THF, MeOH, MeCN, DMSO, and DMF.14
Ramachary et al.15 reported an organocatalytic enolate-me-
diated synthesis of 1,2,3-triazoles from aldehydes and aryl
azides as starting materials, which constitutes an important
alternative method. Meanwhile, syntheses of 1,5-disubsti-
tuted 1,2,3-triazoles were reported, in which ruthenium or
a base was usually applied as a catalyst.16 Recently, 1,4,5-
trisubstituted 1,2,3-triazoles have been synthesized by us-
ing a three-component system or from starting materials
other than terminal alkynes and azides.17 Some simple one-
pot syntheses have been demonstrated that use aryldi-
azonium silica sulfates,18 arylboronic acids,19 aryl halides,20
or aromatic amines21 as starting materials.
DOI: 10.1055/s-0036-1589157; Art ID: st-2017-w0753-l
Abstract A one-pot synthesis of 1-monosubstituted-1,2,3-triazoles
from propargyl alcohol and various aryl azides was achieved. This sim-
ple method provides concise and efficient access to various 1-mono-
substituted 1,2,3-triazole derivatives through a three-step one-pot
sequence in good to excellent yields.
Key words triazoles, propargyl alcohol, aryl azides, copper catalysis
As an important group of heterocyclic compounds con-
taining a five-membered ring with three nitrogen atoms,
1,2,3-triazole derivatives are widely applied in many fields,
such as biology,1 materials science,2 and medicinal3 and
synthetic organic chemistry.4 In particular, in the last ten
years many compounds of this type have found use as clini-
cal and commercial drugs such as antibiotics,5 indoleamine
2,3-dioxygenase (IDO) inhibitors,6 antiviral drugs,7 and
histone deacetylase inhibitors (HDIs) (Figure 1).8
N
N
N
HO
RO
N
NH
OH
NH
N
O
R
N
O
(CH2)n
R = H, Cl, Br
n = 4–8
HDIs
IDO inhibitor
O
N
N
H
O
O
S
N
CO2Et
H
N
AcO
N
N
N
O
AcO
OAc
COOH
Antibiotic
Antiviral drug
Figure 1 Some 1,2,3-triazoles possessing various pharmaceutical
activities
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E

B
C. Han et al.
Letter
Synlett
Owing to their recently identified particular biological
activity, 1-monosubstituted 1,2,3-triazole derivatives have
attracted a great deal of attention, especially in relation to
their preparation, and they have been mainly prepared
from azides and various acetylene sources, including
acetylene22 and its derivatives, such as acetylides
[ethynyl(trimethyl)silane, ethynyl(tributyl)tin, sodium
acetylide, or calcium carbide];23 vinyl compounds (vinyl
acetate, vinyl ethers, vinyl amines, or vinyl sulfoxides);24 or
propiolic acid (Scheme 1).25
Na
Sn(nBu)3
SiMe3
Ca
N
N
O2CR'
N
R
OR'
CO2H
As part of our continuing interest in the synthesis and
modification of various 1,2,3-triazole derivatives,26 we de-
scribe a convenient and efficient one-pot three-step meth-
od for the preparation of monosubstituted 1,2,3-triazoles 3
O2SR'
NR'R''
Scheme 1 Methods for synthesizing 1-monosubstituted 1,2,3-triazoles
Table 1 Selected Optimizations of the Reaction Conditionsa
1) CuI, NaAsc, Solvent, 80 °C
2) Oxidant 1, Base, 80 °C
N
N
N3
+
N
OH
3) Cat., Oxidant 2, 100 °C
1a
2
3a
Entry
Solvent
Oxidant 1 (2.5 equiv) Base (1.5 equiv)
Catalyst (mol%)
Oxidant 2 (2 equiv)
Yieldb (%)
1
2
DMF
–
–
–
–
62c
76c
68c
96c
74d
88d
72d
82d
86d
92d
0e
DMF–H2O (8:1)
MeCN–H2O (8:1)
MeCN
–
–
–
–
3
–
–
–
–
4
–
–
–
–
5
MeCN
tBuOOH
K2S2O8
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
KMnO4
–
–
–
6
MeCN
–
–
–
7
MeCN
–
–
–
8
MeCN
KOH
–
–
9
MeCN
K2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
–
–
10
11
12
13
14
15
16
17
18
19
20
21
22
MeCN
–
–
MeCN
PdCl2 (20)
Pd(OAc)2 (20)
AgOAc (20)
AgOAc (20)
Ag2CO3 (20)
AgNO3 (20)
Ag2O (20)
Ag2O (20)
Ag2O (20)
Ag2O (20)
Ag2O (10)
Ag2O (5)
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
K2S2O7
K2S2O7
K2S2O7
K2S2O7
(NH4)2S2O7
KMnO4
–
MeCN
25e
30e
36e
30e
52e
86e
74e
26e
32e
88e
65e
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
K2S2O7
K2S2O7
MeCN
a Reaction conditions: (1) 1-azido-4-methylbenzene (1a; 0.3 mmol), propargyl alcohol (2; 0.36 mmol), CuI (0.03 mmol), NaAsc (0.06 mmol), solvent (2 mL)
solvent, 15 mL sealed pressure tube, stirring, 80 °C; (2) oxidant 1 (0.75 mmol), base (0.45 mmol), stirring, 80 °C; (3) catalyst and oxidant 2 (0.6 mmol), stirring,
100 °C.
b Isolated yield.
c Yield of [1-(4-tolyl)-1H-1,2,3-triazol-4-yl]methanol.
d Yield of 1-(4-tolyl)-1H-1,2,3-triazole-4-carboxylic acid.
e Yield of 1-(4-tolyl)-1H-1,2,3-triazole (3a).
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E

C
C. Han et al.
Letter
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by using aryl azides 1 and propargyl alcohol (2) as starting
materials.
10). t-BuOOH, K2S2O8, KMnO4, KMnO4–KOH, and KMnO4–
K2CO3 gave inferior results as oxidants (entries 5–9). En-
couraged by these results, we screened various catalysts
and oxidants for the final step of the process (entries 11–
20). None of the target molecule was detected when we
used PdCl2 as a catalyst and Cu(OAc)2 as the oxidant (entry
11). When the PdCl2 catalyst was replace with Pd(OAc)2, the
reaction gave 1-(4-tolyl)-1H-1,2,3-triazole (3a) in 25% yield
(entry 12). We then investigated other catalysts (AgOAc,
Ag2CO3, AgNO3, and Ag2O) (entries 13–17) and we found
that Ag2O was the most efficient. Oxidant screening showed
that K2S2O7 was the best choice, giving an 86% yield (entry
17). An oxidant is essential for this coupling, as a very low
yield was obtained in the absence of an oxidant (entry 20).
Next, we examined the amount of Ag2O and we found that
10% AgNO3 was efficient in this transformation, affording
the desired product 3a in 88% yield (entry 21); reducing the
amount to 5% an inferior result was obtained(entry 22).
We chose the reaction of 1-azido-4-methylbenzene (1a)
and propargyl alcohol (2) as a model system (Table 1). Ini-
tially, we explored the first step of the process by using CuI
and sodium ascorbate (NaAsc) as a catalyst system in vari-
ous solvents, and we obtained the intermediate product [1-
(4-tolyl)-1H-1,2,3-triazol-4-yl]methanol in 62% yield by us-
ing DMF as a solvent, through a Cu-catalyzed azide–alkyne
Huisgen cycloaddition (Table 1, entry 1). DMF–H2O (8:1),
MeCN–H2O (8:1), and MeCN were also examined as sol-
vents, and an excellent yield of 96% was obtained in MeCN
after five hours (entries 2–4). We then studied the second
process of oxidizing the intermediate product [1-(4-tolyl)-
1H-1,2,3-triazol-4-yl]methanol to 1-(4-tolyl)-1H-1,2,3-tri-
azole-4-carboxylic acid by using various oxidants and bases
(entries 5–10). A combination of KMnO4 and Na2CO3 was
the best choice, giving a 92% yield after eight hours (entry
Table 2 Substrates scopea,b
3) Oxidant 2,
Cat., 100 °C
1) CuI, NaAsc,
N
2) Oxidant 1,
Base, 80 °C
N
N
N
N
Solvent, 80 °C
N
N
p-Tol N3
N
+
p-Tol
N
p-Tol
p-Tol
OH
CO2H
1a
2
5a
3a
4a
OH
N
N
N
N
N
N
N
N
N
3a; 88%
3b; 83%
3c; 81%
MeO
N
N
N
N
N
N
OMe
NO2
F
N
N
N
3e; 93%
3d; 83%
3f; 87%
O2N
N
N
N
N
N
N
N
SO2NH2
N
N
3g; 79%
3h; 73%
3i; 70%
F
Cl
Br
N
N
N
N
N
N
N
N
N
3k; 76%
3j; 70%
3l; 73%
Cl
N
N
N
N
N
N
N
Cl
N
N
3n; 81%
3m; 75%
3o; 77%
Br
N
N
N
N
N
Br
N
3q; 82%
3p; 80%
a Reaction conditions: (1) azide 1 (0.3 mmol), propargyl alcohol (2; 0.36 mmol), CuI (0.03 mmol), NaAsc (0.06 mmol), MeCN (2 mL), sealed 15 mL pressure tube,
80 °C, 5 h. (2) KMnO4 (0.75 mmol), Na2CO3 (0.45 mmol), 80 °C, 8 h; (3) Ag2O (0.03 mmol), K2S2O7 (0.6 mmol), 100 °C, 24 h.27
bYields of the isolated products after column chromatography are reported.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E

D
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By using the optimized reaction conditions, we then ex-
plored the scope of the aryl azide in this transformation
(Table 2). A broad spectrum of substrates bearing various
substituents was investigated. All the reactions proceeded
smoothly and they consistently gave the target molecules
3a–q in good to excellent yield, regardless of whether the
substrates bore electron-donating or electron-withdrawing
substituents (Table 2, 3a–q). The reactions of aryl azides
with electron-donating groups such as methyl or methoxy
in the ortho-, meta-, or para-position all gave the corre-
sponding products in good yields (3a–f). Substrates with an
electron-withdrawing group such as as sulfonamide, nitro,
fluoro, chloro, or bromo also reacted smoothly, although
the yields were somehow lower (2g–q).
Aryl azides with substituents in the para-position pro-
duced higher yields than did those bearing groups in the
meta- or ortho-position, probably owning to the steric ef-
fects (Table 2, 3a versus 3c and 3d or 3e versus 3f). Note
that substrates possessing more-electron-rich groups gave
higher yields of the corresponding products. Furthermore, a
substrate bearing group a sulfonamido group was also suit-
able for this transformation, giving a good yield of the cor-
responding product 3g.
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In summary, we successfully synthesized 1-monosub-
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aryl azides as starting materials. The 1-monosubstituted
1,2,3-triazole derivatives were readily prepared in good to
excellent yields by a simple three-step one-pot sequence.
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Funding Information
The authors would like to thank the National Natural Science Founda-
tion of China (No. 51464021) for financial support.
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Supporting Information
Supporting information for this article is available online at
https://doi.org/10.1055/s-0036-1589157.
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reduced pressure to afford a crude product that was purified by
column chromatography [silica gel, EtOAc–PE (1:3)].
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(27) 1-Substituted 1H-1,2,3-Triazoles; General Procedure
Aryl azide 1 (0.3 mmol), propargyl alcohol (2; 0.36 mmol), CuI
(0.03 mmol), NaAsc (0.06 mmol), and MeCN (2 mL) were added
to a 15 mL pressure tube. The tube was sealed and the mixture
was stirred at 80 °C for 5 h until the reaction was complete.
KMnO4 (0.75 mmol) and Na2CO3 (0.45 mmol) were added, and
the mixture was stirred at 80 °C for 8 h. Ag2O (0.03 mmol) and
K2S2O7 (0.6 mmol) were then added, and the mixture was
heated at 100 °C for 24 h until the reaction was complete (TLC).
H2O (25 mL) was added, and the mixture was extracted with
EtOAc (3 × 20 mL). The organic layers were combined, washed
with brine (3 × 5 mL), dried (Na2SO4), and concentrated under
White solid; yield: 42 mg (88%); mp 85.5–86.5 °C. 1H NMR (500
MHz, CDCl3): δ = 7.96 (d, J = 0.8 Hz, 1 H), 7.83 (s, 1 H), 7.62 (d,
J = 8.4 Hz, 2 H), 7.32 (d, J = 8.2 Hz, 2 H), 2.43 (s, 3 H).
1-(2-Methoxyphenyl)-1H-1,2,3-triazole (3f)
White solid; yield: 46 mg (87%); mp 81–82.3 °C. 1H NMR (400
MHz, CDCl3): δ = 8.13 (d, J = 1.0 Hz, 1 H), 7.82 (d, J = 1.0 Hz, 1 H),
7.79 (dd, J = 7.9, 1.7 Hz, 1 H), 7.46–7.41 (m, 1 H), 7.14–7.08 (m, 2
H), 3.89 (s, 3 H).
4-(1H-1,2,3-Triazol-1-yl)benzenesulfonamide (3g)
White solid; yield: 53 mg (79%); mp 187–187.5 °C. 1H NMR (500
MHz, CDCl3): δ = 8.93 (s, 1 H), 8.14 (d, J = 8.6 Hz, 2 H), 8.04 (d,
J = 6.1 Hz, 3 H), 7.55 (s, 2 H).
1-(3-Chlorophenyl)-1H-1,2,3-triazole (3m)
White solid; yield: 40 mg (75%); mp 91.6–92.4 °C. 1H NMR (400
MHz, CDCl3): δ = 8.02 (d, J = 1.1 Hz, 1 H), 7.86 (d, J = 1.0 Hz, 1 H),
7.80 (t, J = 2.0 Hz, 1 H), 7.66 (ddd, J = 7.9, 2.0, 1.3 Hz, 1 H), 7.51–
7.40 (m, 2 H).
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E