1,2,3-Triazole synthesis
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Synthesis of 1,2,3-triazoles and benzotriazoles
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The synthesis of 1-monosubstituted aryl 1,2,3-triazoles was achieved in good
yields using calcium carbide as a source of acetylene. The copper-catalyzed
1,3-dipolar cycloaddition reactions were carried out without nitrogen protection
and in a MeCN-H2O mixture.
Y. Jiang, C. Kuang, Q. Yang, Synlett, 2009,
p-TsOH is a vital additive in the 1,3-dipolar cycloaddition of
nitroolefins and sodium azide. This p-TsOH-mediated cycloaddition enables
a rapid synthesis of valuable 4-aryl-NH-1,2,3-triazoles in high yields.
X.-J. Quan, Z.-H. Ren, Y.-Y. Wang, Z.-H. Guan, Org. Lett.,
A Pd-catalyzed synthesis of 1H-triazoles from alkenyl halides and
sodium azide represents a completely new reactivity pattern in the context of Pd
chemistry.
J. Barluenga, C. Valdés, G. Beltrán, M. Escribano, F. Aznar, Angew. Chem. Int. Ed., 2006, 45, .
J. Barluenga, C. Valdés, G. Beltrán, M. Escribano, F. Aznar, Angew. Chem. Int. Ed., 2006, 45, .
A regioselective one-pot synthesis of 1,5-disubstituted 1,2,3-triazoles through
N/C-heterocyclization of allenylindium bromide across aryl azides is carried out
under mild conditions in aqueous medium and proceeds in good yields.
A. H. Banday, V. J. Hruby,
Synlett, 2014, 25, .
A tandem catalysis protocol based on decarboxylative coupling of alkynoic acids
and 1,3-dipolar cycloaddition of azides avoids usage of gaseous or highly
volatile terminal alkynes, reduces handling of potentially unstable and
explosive azides to a minimum, and furnishes various functionalized
1,2,3-triazoles in excellent yields and a very good purity without the need for
additional purification.
A. Kolarovič, M. Schnürch, M. D. Mihovilovic, J. Org. Chem., 2011,
Self-assembly of copper sulfate and a poly(imidazole-acrylamide) amphiphile
provides a highly active, reusable, globular, solid-phase catalyst for click
chemistry. The insoluble amphiphilic polymeric imidazole Cu catalyst drove the
cycloaddition of various of alkynes and organic azides at very low catalyst
loadings and can be readily reused without loss of activity to give the
corresponding triazoles quantitatively.
Y. M. A. Yamada, S. M. Sarkar, Y. Uozumi, J. Am. Chem. Soc., 2012,
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3-dibromopropanoic
acids and sodium azide by using inexpensive copper(I) iodide as the catalyst in
the presence of cesium carbonate as base and DMSO as solvent.
Y. Jiang, C. Kuang, Q. Yang, Synthesis, 2010,
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3-dibromopropanoic
acids and sodium azide by a one-pot method using N,N-dimethylformamide as
solvent in the presence of Pd2(dba)3 and Xantphos.
W. Zhang, C. Kuang, Q. Yang, Synthesis, 2010,
1-Substituted-1,2,3-triazoles were conveniently synthesized from the
corresponding aromatic and aliphatic azides in the presence of acetylene gas
using mild, copper(I)-catalyzed ‘click chemistry'.
L.-Y. Wu, Y.-X. Xie, Z.-S. Chen, Y.-N. Niu, Y.-M. Liang, Synlett, 2009,
A true Click catalytic system is based on commercially available [CuBr(PPh3)3].
This system is active at room temperature, with catalyst loadings of 0.5 mol %
or less, in the absence of any additive, and it does not require any
purification step to isolate pure triazoles.
S. Lal, S. Díez-González, J. Org. Chem., 2011,
Acid-Base Jointly Promoted Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
C. Shao, X. Wang, Q. Zhang, S. Luo, J. Zhao, Y. Hu, J. Org. Chem., 2011,
A well-defined copper(I) isonitrile complex is an efficient, heterogeneous
catalyst for azide-alkyne 1,3-dipolar cycloadditions and three-component
reactions of halides, sodium azide and alkynes to form 1,4-disubstituted
1,2,3-triazoles in high yields under mild conditions in water. The complex can
be recycled for at least five runs without significant loss of activity by
simple precipitation and filtration.
M. Liu, O. Reiser, Org. Lett., 2011,
Cycloadditions of copper(I) acetylides to azides and nitrile oxides provide
ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted
isoxazoles, respectively. The process is highly reliable and exhibits an
unusually wide scope with respect to both components. Computational studies
revealed a nonconcerted mechanism involving unprecedented metallacycle
intermediates.
F. Himo, T. Lovell, R. Hilgraf, V. V. Rostovtsev, L. Noodleman, K. B. Sharpless,
V. V. Fokin, J. Am. Chem. Soc., 2005,
127, 210-216.
An efficient I2/TBPB mediated oxidative formal [4 + 1] cycloaddition
of N-tosylhydrazones with anilines represents a simple, general, and
efficient approach for the construction of 1,2,3-triazoles under metal-free and
azide-free conditions.
Z.-J. Cai, X.-M. Lu, Y. Zi, C. Yang, L.-J. Shen, J. Li, S.-Y. Wang, S.-J. Ji, Org. Lett.,
A mild, zinc-mediated method for regioselective formation of 1,5-substituted
1,2,3-triazoles from a wide range of azides and alkynes works at room
temperature. Additionally, the triazole 4-position can be further functionalized
by reaction of the intermediate aryl-zinc with various electrophiles to
accommodate a diverse three-component coupling strategy.
C. D. Smith, M. F. Greaney, Org. Lett., 2013,
A Ce(OTf)3-catalyzed [3 + 2] cycloaddition of organic azides with
nitroolefins and subsequent elimination reaction selectively produces
1,5-disubstituted 1,2,3-triazoles in very good yields. Both benzyl and phenyl
azides react with a broad range of aryl nitroolefins containing a wide range of
functionalities.
Y.-C. Wang, Y.-Y. Xie, H.-E. Qu, H.-S. Wang, Y.-M. Pan, F.-P. Huang, J. Org. Chem., 2014,
1,5-Diarylsubstituted 1,2,3-triazoles are formed in high yield from aryl
azides and terminal alkynes in DMSO in the presence of a catalytic amount of
tetraalkylammonium hydroxide or t-BuOK for base-labile substrates. The
reaction is experimentally simple, does not require a transition-metal catalyst,
and is not sensitive to atmospheric oxygen and moisture.
S. W. Kwok, J. R. Fotsing, R. J. Fraser, V. O. Rodinov, V. V. Fokin, Org. Lett., 2010,
The use of t-BuOK in wet DMF as desilylating reagent in a cycloaddition
reaction of aromatic azides and trimethylsilyl alkynes generated
1,5-disubstituted 1,2,3-triazoles regioselectively in good yields at ambient
temperature.
L. Wu, X. Chen, M. Tang, X. Song, G. Chen, X. Song, Q. Lin, Synlett, 2012, 23,
A Cu/Pd transmetalation relay catalysis enables a three-component click reaction
of azide, alkyne, and aryl halide to yield 1,4,5-trisubstituted 1,2,3-triazoles
in one step in high yields with complete regioselectivity. This reaction offers
an alternative to the well-established CuAAC click reactions only working on
terminal alkynes.
F. Wei, H. Li, C. Song, Y. Ma, L. Zhou, C.-H. Tung, Z. Xu, Org. Lett.,
In the presence Cp*RuCl(PPh3)2 or Cp*RuCl(COD) as catalyst,
primary and secondary azides react with a broad range of terminal alkynes
containing a range of functionalities selectively producing 1,5-disubstituted
1,2,3-triazoles. Both complexes also promote the cycloaddition reactions of
organic azides with internal alkynes, providing access to fully-substituted
1,2,3-triazoles.
B. C. Boren, S. Narayan, L. K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V.
V. Fokin, J. Am. Chem. Soc., 2008,
In the presence of inexpensive copper (I) iodide as the catalyst, a series of
1,4-disubstituted 1,2,3-triazoles were synthesized in a one-pot process from
anti-3-aryl-2,3-dibromopropanoic acids and organic azides in dimethyl
sulfoxide.
X. Chen, Y. Yang, C. Kuang, Q. Yang, Synthesis, 2011,
A copper(I)-catalyzed three-component reaction of amines, propargyl halides and
azides forms 1-substituted-1H-1,2,3-triazol-4-ylmethyl)-dialkylamines in
water. Synthetic advantages are high atom economy, low environmental impact,
atmospheric oxygen, wide substrate scope, mild reaction condition and good
Z.-Y. Yan, Y.-B. Zhao, M.-J. Fan, W.-M. Liu, Y.-M. Liang, Tetrahedron, 2005,
A method for the regiospecific synthesis of
1,4,5-trisubstituted-1,2,3-triazole catalyzed by copper(I) iodide was developed.
This is the first example of a regiospecific synthesis of
5-iodo-1,4-disubstituted-1,2,3-triazole, which can be further elaborated to a
range of 1,4,5-trisubstituted-1,2,3-triazole derivatives.
Y.-M. Wu, J. Deng, Y. L. Li, Q.-Y. Chen, Synthesis, 2005,
Inexpensive copper catalysts enabled modular one-pot multicomponent syntheses
of fully decorated triazoles through a sustainable “click” reaction/direct
arylation sequence.
L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett.,
L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett.,
Microwave irradiation significantly enhances the rate of formation of
1,4-disubstituted 1,2,3-triazoles from alkynes and in situ generated azides.
Azides are derived from an efficient one-pot azidation of anilines with the
reagent combination t-BuONO and TMSN3.
A. D. Moorhouse, J. E. Moses, Synlett, 2008,
A reliable and operationally simple one-pot reaction for a one-carbon
homologation of various aldehydes followed by Cu-catalyzed azide-alkyne click
chemistry gives 1,4-disubstituted 1,2,3-triazoles in good yields without the
need for isolation of the alkyne intermediates.
D. Luvino, C. Amalric, M. Smietana, J.-J. Vasseur, Synlett, 2007,
1,2,3-Triazoles were prepared in good to modest yields by cycloaddition of
alkyl azides onto enol ethers under solventless conditions. The reaction can
access ring-fused triazoles that are unavailable by azide-alkyne cycloadditions
and is easily scalable. The 1,2,3-triazole products bear functionality that may
be readily derivatized.
D. R. Rogue, J. L. Neill, J. W. Antoon, E. P. Stevens, Synthesis, 2005, .
Triazoles have been synthesized via a three-component coupling reaction of
unactivated terminal alkynes, allyl carbonate, and trimethylsiyl azide under
Pd(0)-Cu(I) bimetallic catalysis. The deallylation of the resulting
allyltriazoles is described.
S. Kamijo, T. Jin, Z. Huo, Y. Yamamoto, J. Am. Chem. Soc., 2003, 125, .
Reaction of 4-bromo-NH-1,2,3-triazoles with alkyl halides in the presence
of K2CO3 in DMF produced the corresponding 2-substituted
4-bromo-1,2,3-triazoles in a regioselective process. Subsequent Suzuki
cross-coupling reaction provided an efficient synthesis of 2,4,5-trisubstituted
triazoles, whereas hydrogenation furnished an efficient synthesis of
2,4-disubstituted triazoles.
X.-j. Wang, K. Sidhu, L. Zhang, S. Campbell, N. Haddad, D. C. Reeves, D.
Krishnamurthy, C. H. Senanayake, Org. Lett., 2009,
A palladium-catalyzed and ultrasonic promoted Sonogashira coupling/1,3-dipolar
cycloaddition of acid chlorides, terminal acetylenes, and sodium azide in one
pot enables an efficient synthesis of 4,5-disubstituted-1,2,3-(NH)-triazoles in
excellent yields.
J. Li, D. Wang, Y. Zhang, J. Li, B. Chen, Org. Lett., 2009,
TBAF-catalyzed [3 + 2] cycloadditions of 2-aryl-1-cyano- or
2-aryl-1-carbethoxy-1-nitroethenes with TMSN3 under solvent free
conditions allow the preparation of 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles under mild reaction conditions with good to excellent yields.
D. Amantini, F. Fringuelli, O. Piermatti, F. Pizzo, E. Zunino, L. Vaccaro, J. Org. Chem., 2005, 70, .
D. Amantini, F. Fringuelli, O. Piermatti, F. Pizzo, E. Zunino, L. Vaccaro, J. Org. Chem., 2005, 70, .
Triazole-based monophosphine ligands have been prepared via efficient
cycloadditions. Palladium complexes derived from these ligands are highly
active catalysts for Suzuki-Miyaura coupling and amination reactions of aryl
chlorides.
D. Liu, W. Gao, Q. Dai, X. Zhang, Org. Lett.,
2005, 7, .
A highly efficient method for the synthesis of multisubstituted 1,2,3-triazoles
via a direct Pd-catalyzed C-5 arylation has been developed.
S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org. Lett., 2007,
The use of nontoxic polyethylene glycol (PEG) as solvent and MesCO2H
as cocatalyst enabled user-friendly palladium(0)-catalyzed C-H bond
functionalizations under air in the absence of phosphine ligands. Direct
arylations of 1,2,3-triazoles gave substituted triazoles in good yields.
Recycling of the catalytic system led to a slight decrease of activity.
L. Ackermann, R. Vicente, Org. Lett., 2009,
Conditions for the palladium-catalyzed direct arylation of a wide range of
heterocycles with aryl bromides employ a stoichiometric ratio of both coupling
partners, as well as a substoichiometric quantity of pivalic acid, which results
in significantly faster reactions. An evaluation of the influence of the nature
of the aryl halide has also been carried out.
B. Liégault, D. Lapointe, L. Caron, A. Vlassova, K. Fagnou, J. Org. Chem., 2009,
A copper-catalyzed [3 + 2] cycloaddition/oxidation reaction of nitro-olefins
with organic azides affords a broad range of 1,4(-NO2),5-trisubstituted
1,2,3-triazoles with high regioselectivities and in very good yields without
elimination of HNO2.
Y. Chen, G. Nie, Q. Zhang, S. Ma, H. Li, Q. Hu, Org. Lett.,
A ruthenium-catalyzed cycloaddition of N-Boc ynamides with azides gives
protected 5-amino-1,2,3-triazole-4-carboxylic acids, which are suitable for the
preparation of peptidomimetics. When aryl or alkyl azides are reacted with N-Boc-aminopropiolates
or arylynamides, the cycloaddition occurs with complete regiocontrol, while N-Boc-alkyl
ynamides yield a mixture of regioisomers.
S. Ferrini, J. Z. Chandanshive, S. Lena, M. C. Franchini, G. Giannini, A. Tafi,
M. Taddei, J. Org. Chem.,
A cyclocondensation of 2-(arylamino)aryliminophosphoranes enables the synthesis
of 1-aryl-1,2,3-benzotriazoles under mild conditions. The reaction involves a
three-step, halogen-free route starting from simple nitroarenes and arylamines.
E. Łukasik, Z. Wróbel,
Synlett, 2014, 25, .
A [3 + 2] cycloaddition of azides to benzynes affords a rapid and easy entry to
a variety of substituted, functionalized benzotriazoles under mild conditions.
F. Shi, J. P. Waldo, Y. Chen, R. C. Larock, Org. Lett., 2008,
A 1,7-palladium migration-cyclization-dealkylation sequence for the
regioselective synthesis of benzotriazoles proceed in excellent yields with high
regioselectivities. The mechanism of the reaction has also been investigated.
J. Zhou, J. He, B. Wang, W. Yang, H. Ren, J. Am. Chem. Soc., 2011,
C-H activation of aryl triazene compounds followed by intramolecular amination
in the presence of a catalytic amount of Pd(OAc)2 provides 1-aryl-1H-benzotriazoles
at moderate temperature.
R. K. Kumar, M. A. Ali, T. Punniyamurthy, Org. Lett., 2011,
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扫一扫发现精彩That sounds good 1、改为一般疑问句并否定回答 2、改为否定句
你好,知道英语牛人团为你解答.1 -一般疑问句：Does that sound good?否定回答：No. That doesn't sound good.2 -这句话的意思是说“这听起来是个好主意.”否定的话,可以有两种表述：“这听起来不是个好主意”或者“这听起来是个坏主意”.因此解答也就有两种方式：第一种对应的英文是：That doesn't sound good.第二种对应的英文是：That sounds awful.就题目本身来看,标准答案可能更偏爱直接语法上的否定,所以我觉得第一种更容易得分.两种都写出来,供你参考 :-)
为什么用Does
不用Is that ？
是这样的，这句话当中动词是sound，改写疑问句的时候，需要把助动词请出来提到前面来帮忙。类似的句子其实非常多：He likes swimming.DOES he like swimming?这里的动词是like，改疑问句的时候助动词DOES提前。
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