Ultrasound-promoted organocatalytic enamine-azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

Article abstract of DOI:10.3762/bjoc.13.68

The use of sonochemistry is described in the organocatalytic enamine-azide [3 + 2] cycloaddition between 1,3-diketones and aryl azidophenyl selenides. These sonochemically promoted reactions were found to be amenable to a range of 1,3-diketones or aryl az

Full text of DOI:10.3762/bjoc.13.68

Ultrasound-promoted organocatalytic enamine–azide
[3 + 2] cycloaddition reactions for the synthesis of
((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones
Gabriel P. Costa1, Natália Seus1, Juliano A. Roehrs1, Raquel G. Jacob1,
Ricardo F. Schumacher1, Thiago Barcellos2, Rafael Luque*3 and Diego Alves*1
Full Research Paper
Open Access
Address:
Beilstein J. Org. Chem. 2017, 13, 694–702.
1Laboratório de Síntese Orgânica Limpa - LASOL - CCQFA -
Universidade Federal de Pelotas - UFPel - P.O. Box 354 - 96010-900,
Pelotas, RS, Brazil, 2Laboratory of Biotechnology of Natural and
Synthetic Products, Universidade de Caxias do Sul, Caxias do Sul,
RS, Brazil and 3Departamento de Quimica Organica, Universidad de
Cordoba, Campus de Rabanales, Cordoba, Spain
doi:10.3762/bjoc.13.68
Received: 14 December 2016
Accepted: 22 February 2017
Published: 11 April 2017
This article is part of the Thematic Series "Green chemistry".
Guest Editor: L. Vaccaro
Email:
Rafael Luque* - q62alsor@uco.es; Diego Alves* -
diego.alves@ufpel.edu.br
© 2017 Costa et al.; licensee Beilstein-Institut.
License and terms: see end of document.
* Corresponding author
Keywords:
cycloadditions; organocatalysis; organoselenium compounds;
sonochemistry; 1,2,3-triazoles
Abstract
The use of sonochemistry is described in the organocatalytic enamine–azide [3 + 2] cycloaddition between 1,3-diketones and aryl
azidophenyl selenides. These sonochemically promoted reactions were found to be amenable to a range of 1,3-diketones or aryl
azidophenyl selenides, providing an efficient access to new ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones in good to excellent
yields and short reaction times. In addition, this protocol was extended to β-keto esters, β-keto amides and α-cyano ketones.
Selanyltriazoyl carboxylates, carboxamides and carbonitriles were synthesized in high yields at short times of reaction under very
mild reaction conditions.
Introduction
Substituted 1,2,3-triazoles are an interesting class of hetero- [16-19]. More recently, transition metal catalysts based on
cyclic compounds distinguished by their biological activities copper, ruthenium, silver and iridium salts have been used for
[1-3] as well as in various fields of chemistry [4-15]. The most this cycloaddition reaction [20-29].
attractive way for their preparation is the thermal 1,3-dipolar
cycloaddition of alkynes and azides, introduced by Huisgen Organocatalytic approaches based on β-enamine–azide or
which usually gives rise to a mixture of 1,4 and 1,5-isomers enolate–azide cycloadditions have been employed to synthesize
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Beilstein J. Org. Chem. 2017, 13, 694–702.
1,2,3-triazole scaffolds [30-32]. Depending on the organocata- reduce the number and quantities of side reaction products [62-
lyst employed, different carbonyl compounds could successful- 67].
ly generate an enamine or an enolate, and these species react as
dipolarophiles with organic azides in organocatalyzed 1,3- There are only a few contributions describing the use of sono-
dipolar cycloadditions. Our research group has demonstrated chemistry for the preparation of functionalized 1,2,3-triazoles
β-enamine–azide cycloaddition reactions for the synthesis of [68-74]. As a recent example, our research group described the
selenium-functionalized 1,2,3-triazoles [33-37]. Selanyltriazoyl use of sonochemistry in the organocatalytic enamine–azide
carboxylates, carboxamides, carbonitriles or sulfones were syn- [3 + 2] cycloadditions of β-oxo-amides with a range of substi-
thesized in good to excellent yields using catalytic amounts of tuted aryl azides providing and efficient access to new N-aryl-
an organocatalyst.
1,2,3-triazoyl carboxamides in good to excellent yields and
short reaction times of [75].
Organoselenium compounds are attractive synthetic targets
because of their selective reactions [38-43], photophysical prop- However, to the best of our knowledge, the use of sonochem-
erties [44-49] and interesting biological activities [50-52]. An istry to synthesize complex selenium-functionalized 1,2,3-tri-
interesting class of molecules are the selanyl-1,2,3-triazoles azoles via organocatalytic enamine–azide cycloaddition has not
[53-61] which can present some biological applications. As ex- been explored to date. As a continuation of our ongoing studies
ample, 4-phenyl-1-(phenylselanylmethyl)-1,2,3-triazole A (Se- towards the development of new 1,2,3-triazoles bearing
TZ) demonstrated an antidepressant-like effect (Figure 1) [60]. organoselenium moieties, this contribution was aimed to
In another example, 5-phenyl-1-(2-(phenylselanyl)phenyl)-1H- disclose a sonochemical approach for the organocatalyzed
1,2,3-triazole-4-carbonitrile B (Se-TZCN) was reported to ex- synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones
hibit antioxidant activities in different in vitro assays (Figure 1) by reacting a range of 1,3-diketones with substituted aryl
[36]. Selenanyl-quinone-based 1,2,3-triazoles C and D were azidophenyl selenides (Scheme 1).
synthesized and evaluated against six types of cancer cell lines.
The synthesized compounds emerge as promising molecules for Results and Discussion
the therapeutic use of cancers overexpressing NQO1 (Figure 1) Due to the fact that organocatalyzed β-enamine–azide cycload-
[61].
dition reactions between azidophenyl aryl selenides and
1,3-diketones were not described, preliminary studies were
Thus, the search for efficient methods using appropriate and en- attempted to react 2-azidophenyl phenyl selenide (1a) and 2,4-
vironmentally sound substrates for the preparation of selenium- pentanedione (2a) as model reaction substrates. Based on our
functionalized 1,2,3-triazoles still remains a challenge in previous report on such reaction [33], a mixture of substrates
organic synthesis.
1a (0.3 mmol) and 2a (0.3 mmol) in DMSO (0.6 mL) was
stirred at room temperature in the presence of 1 mol % of
Ultrasonic irradiation has emerged in the past decades as a Et2NH as organocatalyst, providing an excellent yield
versatile tool in industrial and academic applications [62-67]. (98%) of the desired product 3a after 2 h (conditions A,
The use of sonication in organic synthesis (sonochemistry) is Scheme 2).
well documented and is generally considered as an environmen-
tally sound energy source, comparatively less energy intensive With the aim to compare the effect of different energy sources
to conventional heating and microwave irradiation, also able to in this β-enamine–azide cycloaddition, the reaction between
Figure 1: Biologically relevant selanyl-1,2,3-triazoles.
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Beilstein J. Org. Chem. 2017, 13, 694–702.
Scheme 1: General scheme of the reaction.
Scheme 2: Comparative study of the conventional conditions and ultrasound irradiation. Conditions A: Reaction at 25 °C for 2 h (3a, 98%);
Conditions B: Reaction under ultrasound irradiation (20% of the amplitude) at 25 °C for 20 min (3a, 92%).
substrates 1a and 2a in DMSO using Et2NH (1 mol %) was also Initially, substrates 1a and 2a were reacted in DMSO under
performed under ultrasound irradiation.
ultrasound irradiation for 20 min using different amplitudes
(Table 1, entries 1–4). We observed that the desired product 3a
was obtained in excellent yields in all reactions. However,
product yield of 3a decreased to 70% (Table 1, entry 5) in
10 minutes under 20% sonochemistry amplitude. To our
delight, reactions performed using 40% of amplitude during 10
or 5 min gave excellent yields of selanyltriazole 3a (Table 1,
entries 6 and 7). We observed that the amplitude effect could be
The reaction performed under ultrasound irradiation with 20%
of the amplitude for 20 minutes (followed by TLC until the total
consumption of the starting materials) yielded product 3a in
92% (conditions B, Scheme 2). Inspired by results described
under conditions B, we performed additional experiments using
ultrasound irradiation with Et2NH as organocatalyst (Table 1).
Table 1: Optimization of reaction conditions.a
Entry
Amplitude
Et2NH (mol %)
Time (min)
Yield 3a (%)b
1
2
20
25
30
40
20
40
40
40
40
40
40
40
1
1
20
20
20
20
10
10
5
92
92
3
1
93
4
1
96
5
1
70
6
1
95
7
1
93
8
0.5
0.1
–
25
60
60
5
85
9
n.d.
n.d.
27
10
11c
12d
1
1
5
85
aReactions were performed with 2-azidophenyl phenyl selenide (1a, 0.3 mmol) and 2,4-pentanedione (2a, 0.3 mmol) in DMSO (0.6 mL) as solvent
under ultrasound irradiation at 25 °C. bYields are given for isolated products. cReaction was performed with L-proline as a catalyst. dReaction was
performed with pyrrolidine (1 mol %). n.d.: not detected.
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Beilstein J. Org. Chem. 2017, 13, 694–702.
correlated to the product formation time, since that in reaction steric hindrance effect in 2,2,6,6-tetramethyl-3,5-heptanedione
carried out in 40% of amplitude the yield of compound 3a was 2d displays an important role in the overall reaction and only
excellent (93%) after 5 min reaction time (Table 1, entry 5 vs traces of product 3d was observed (Table 2, entries 1–3 vs 4).
7). A slight decrease in reaction yields could be observed after Unfortunately, no reaction occurred when cyclic β-diketone 2e
decreasing the loading of organocatalyst to 0.5 mol % (Table 1, was employed as substrate (Table 2, entry 5). We next evalu-
entry 8). Finally, in blank runs (in the absence of organocata- ated the reactivity of 2,4-pentanedione (2a) with different func-
lyst) or performed using 0.1 mol % of catalyst the reaction did tionalized aryl azidophenyl selenides 1b–f under identical reac-
not occur, even under sonication for 60 min using 40% of tion conditions. Aryl azidophenyl selenides containing either an
amplitude (Table 1, entries 9 and 10). Reactions performed with EDG or an EWG on the aromatic ring delivered the expected
other catalysts (L-proline and pyrrolidine) gave lower yields of selanyltriazoles 3f–i in good isolated yields (Table 2, entries
3a than those using 1 mol % of Et2NH (Table 1, entry 7 vs 6–9). However, a decrease in yield was observed when the reac-
entries 11 and 12).
tion was performed with aryl azidophenyl selenide containing a
–CF3 group (Table 2, entry 9). In addition, 4-azidophenyl phe-
From Table 1, optimum reaction conditions to obtain 1-(5- nyl selenide (1f) was treated with 2,4-pentanedione (2a) to
methyl-1-(2-(phenylselanyl)phenyl)-1H-1,2,3-triazol-4- afford the desired product 3j in 92% yield as a mixture of regio-
yl)ethan-1-one (3a) were clearly present in entry 7, in which a isomers (6:1) (Table 2, entry 10).
mixture of azidophenyl phenyl selenide (1a, 0.3 mmol), 2,4-
pentanedione (2a, 0.3 mmol) and Et2NH (1 mol %) in DMSO In addition, the possibility to perform the reaction of
(0.6 mL) was sonicated using 40% of amplitude at room tem- 2-azidophenyl phenyl selenide (1a) with β-keto-esters, β-keto-
perature for 5 minutes. In order to extend the scope of the reac- amides and α-cyano-ketones 2f–k was also investigated. The
tion, optimum reaction conditions were extended to other 1,3- reaction conditions optimized for 1,3-diketone 2a were em-
diketones 2a–e with different substitution patterns (Table 2). ployed, but independently using as substrates ethyl acetoacetate
High yields of desired 1,2,3-triazoles were obtained using β-di- (2f), ethyl benzoylacetate (2g), 3-oxo-N-phenylbutanamide
ketones 2a, 2b and 2c bearing methyl, ethyl and phenyl substit- (2h), 3-oxo-N-(p-tolyl)butanamide (2i), benzoylacetonitrile (2j)
uents (Table 2, entries 1–3). However, we observed that the and 4-toluoylacetonitrile (2k). The corresponding esters 3k,l
Table 2: Scope of substrates: Variation of the aryl azidophenyl selenides 1 and 1,3-diketones 2.a
Entry
Aryl azidophenyl
1,3-Diketone 2
Product 3
Isolated Yield (%)b
selenides 1
1
93
2a
1a
3a
2
91
2b
1a
3b
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Beilstein J. Org. Chem. 2017, 13, 694–702.
Table 2: Scope of substrates: Variation of the aryl azidophenyl selenides 1 and 1,3-diketones 2.a (continued)
3
85
1a
2c
3c
4
traces
1a
1a
2d
3d
5
n.d.
2e
3e
6
74
2a
1b
3f
7
84
2a
1c
3g
8
87
2a
1d
3h
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Beilstein J. Org. Chem. 2017, 13, 694–702.
Table 2: Scope of substrates: Variation of the aryl azidophenyl selenides 1 and 1,3-diketones 2.a (continued)
9
56
2a
1e
3i
10
92
2a
1f
3j
aReactions were performed with aryl azidophenyl selenides 1a–f (0.3 mmol) and 1,3-diketones 2a–e (0.3 mmol), using Et2NH (1 mol %) as catalyst in
DMSO (0.6 mL) as solvent under ultrasound irradiation (40% of amplitude) at room temperature for 5 min. bYields are given for isolated products. n.d.:
not detected.
[33], amides 3m,n [34] and nitriles 3o,p [36] were obtained in Comparing these results with already published ones under
good yields (Scheme 3) after 5 minutes reaction under ultra- conventional conditions, our methodology using ultrasound ir-
sound irradiation (40% of amplitude) at room temperature. radiation affords the products in 5 minutes and in comparable
Scheme 3: Reaction of 2-azidophenyl phenyl selenide 1a with activated ketones 2f–k.
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Beilstein J. Org. Chem. 2017, 13, 694–702.
yields while the other methods mostly provide the products in was sonicated for 5 min. The crude product obtained was subse-
times above 60 minutes [33,34,36].
quently purified by column chromatography on silica gel using
a mixture of hexane/ethyl acetate (5:1) as eluent to afford the
desired products 3a–p.
Conclusion
In summary, we have described the use of sonochemistry in the
organocatalytic enamine–azide [3 + 2] cycloaddition between
1,3-diketones and aryl azidophenyl selenides. These sonochem-
ical promoted reactions were found to be amenable to a range of
1,3-diketones or aryl azidophenyl selenides, providing an effi-
cient access to novel selenium-containing 1,2,3-triazole com-
pounds in good to excellent yields, in a few minutes of reaction
at room temperature. The protocol was extended to activated
ketones and selanyltriazoyl carboxylates, with carboxamides
and carbonitriles synthesized in high yields and short times of
reaction.
Supporting Information
Supporting Information File 1
Experimental and analytical data.
[http://www.beilstein-journals.org/bjoc/content/
supplementary/1860-5397-13-68-S1.pdf]
Acknowledgements
We thank the CNPq (Grants 306430/2013-4, 400150/2014-0
and 447595/2014-8), CAPES and FAPERGS (PRONEM 6/
2551-0000240-1) for the financial support. Rafael Luque grate-
fully acknowledges support from Ciência sem Fronteiras
Program (Grant 303415/2014-2) as Visiting Scientist to Univer-
sidade Federal de Pelotas, RS.
Experimental
General information
The reactions were monitored by TLC carried out on Merck
silica gel (60 F254) by using UV light as visualizing agent and
5% vanillin in 10% H2SO4 and heat as developing agents.
Baker silica gel (particle size 0.040–0.063 mm) was used for
flash chromatography. A Cole Parmer-ultrasonic processor
Model CPX 130, with a maximum power of 130 W, operating
at an amplitude of 40% and a frequency of 20 kHz was used.
The temperature of the reaction was monitored using an
Incoterm digital infrared thermometer Model Infraterm (Brazil)
(in most reactions the temperature was in the range between 60
and 65 °C). Proton nuclear magnetic resonance spectra
(1H NMR) were obtained at 400 MHz on Bruker DPX 400
spectrometer. Spectra were recorded in CDCl3 solutions. Chem-
ical shifts are reported in ppm, referenced to tetramethylsilane
(TMS) as the external reference. Coupling constants (J) are re-
ported in Hertz. Abbreviations to denote the multiplicity of a
particular signal are s (singlet), d (doublet), t (triplet),
q (quartet) and m (multiplet). Carbon-13 nuclear magnetic reso-
nance spectra (13C NMR) were obtained at 100 MHz on Bruker
DPX 400 spectrometer. Chemical shifts are reported in ppm,
referenced to the solvent peak of CDCl3. Low-resolution mass
spectra were obtained with a Shimadzu GC-MS-QP2010 mass
spectrometer. High resolution mass spectra (HRMS) were re-
corded on a Bruker Micro TOF-QII spectrometer 10416.
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