Categories: Synthesis of N-Heterocycles >
Synthesis of 1,2,3-triazoles
Recent Literature
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, 6893-6896.
J. Barluenga, C. Valdés, G. Beltrán, M. Escribano, F. Aznar, Angew. Chem. Int. Ed., 2006, 45, 6893-6896.
Highly efficient click chemistry between azides and terminal alkynes can be
heterogeneously catalyzed by copper nanoparticles mounted within the pores of
activated charcoal. Reactions can be accelerated with stoichiometric Et3N
or by increasing the reaction temperature using microwave irradiation.
B. H. Lipshutz, B. R. Taft, Angew. Chem. Int. Ed., 2006,
45, 8235-8238.
The CuI-catalyzed, stepwise cycloaddition of azides to terminal alkynes
exhibits broad scope and provides 1,4-disubstituted 1,2,3-triazoles in
excellent yields and high regioselectivity.
V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., 2002, 114, 2708-2711.
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
yields.
Z.-Y. Yan, Y.-B. Zhao, M.-J. Fan, W.-M. Liu, Y.-M. Liang, Tetrahedron, 2005,
61, 9331-9337.
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,
1314-1318.
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, 2497-2502.
The synthesis of aromatic azides from the corresponding amines is
accomplished under mild conditions with tert-butyl nitrite and
azidotrimethylsilane. 1,4-Disubstituted 1,2,3-triazoles were obtained in
excellent yields from various aromatic amines without the need for isolation of
the azide intermediates.
K. Barral, A. D. Moorhouse, J. E. Moses, Org. Lett., 2007,
9, 1809-1811.
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, 7786-7787.
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, 6526-6529.
D. Amantini, F. Fringuelli, O. Piermatti, F. Pizzo, E. Zunino, L. Vaccaro, J. Org. Chem., 2005, 70, 6526-6529.
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, 4907-4910.
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,
9, 2333-2336.
