Angew Chem Int Ed Engl 47: 1127–1129.
6-е. -М.: URSS, 2012.-421 с.
Tetrahedron Asymmetry 10: 4261–4264.
S.; Kajiki, R.; Hanatani, H.; Kong, X.; Ozoe, F.; Matsui, Y.; Matsumura, F.; Ozoe, Y., Synthesis and Structure-Activity Relationships of 1-Phenyl-1-1,2,3-triazoles as Selective Insect GABA Receptor Antagonists.
A practical and efficient synthesis of triazolothiadiazepine-1,1-dioxide derivatives via copper-catalyzed [3+2]cycloaddition, followed by N-arylation is described. The method is also applicable to the synthesis of indoline- and thiophene-fused triazolothiadiazepine 1,1-dioxide derivatives.
Colloid Interface Sci. 2007, , 491-496.
h.; Selkti, M.; Lavergne, J.-P.; Compain, P., Synthesis of a novel heterocyclic ring system by way of highly regio- and chemoselective 1,3-dipolar cycloaddition of nitrilimines to 1,3,4-benzotriazepin-5-one derivatives.
J.; Buerkstuemmer, E.; Linclau, B., Short Synthesis of Enantiopure 2-Symmetric 1,2:4,5-Diepoxypentane and "Pseudo"-2-Symmetric 3-Azido-1,2:4,5-diepoxypentane from Arabitol.
4. Журнал прикладной спектроскопии. -2012.-Т.79, N 1.
Sharpless, Reengineering Antibiotics to Combat Bacterial Resistance: Click Chemistry [1,2,3]-Triazole Vancomycin Dimers with Potent Activity against MRSA and VRE.
A microwave-assisted one-pot, three-step Sonogashira cross coupling-desilylation-cycloaddition sequence was developed for the convenient preparation of 1,4-disubstituted 1,2,3-triazoles starting from a range of halides, acyl chlorides, ethynyltrimethylsilane and azides.
14. Патенты и лицензии. -2012.-N 1.
17. Письма в Журнал технической физики. -2011.-Т.37, N 24.
3. Ш143.24я2/З18 Зак Ю.А.
Martin, Tsutomu Katsuki (1946-2014), , 54 (16), 4708 (2015).
Application of one-pot synthesis of Cu(I)-catalyzed cycloaddition between azides and terminal alkynes.
19. Физика горения и взрыва. -2012.-Т.48, N 1.
Multi-component one-pot reactions generally afford good yields which is important in combinatorial synthesis.
23. Balkan Journal of Medical Genetics. -2011.-Vol.14, N 2.
In this study 1,4-disubstituted 1,2,3-triazoles were obtained by a high-yielding copper (I) catalyzed 1,3-dipolar cycloaddition reaction between in situ generated azides and terminal acetylenes.
24. Biological Reviews. -2011.-Vol.86, N 4.
N2 - A practical and efficient synthesis of triazolothiadiazepine-1,1-dioxide derivatives via copper-catalyzed [3+2]cycloaddition, followed by N-arylation is described. The method is also applicable to the synthesis of indoline- and thiophene-fused triazolothiadiazepine 1,1-dioxide derivatives.
25. Bulletin of Chemical Society of Japan. -2011.-Vol.84, N 8.
AB - A practical and efficient synthesis of triazolothiadiazepine-1,1-dioxide derivatives via copper-catalyzed [3+2]cycloaddition, followed by N-arylation is described. The method is also applicable to the synthesis of indoline- and thiophene-fused triazolothiadiazepine 1,1-dioxide derivatives.
28. Chemical Physics. -2011.-Vol.384, N 1-3.
The exquisite regioselectivity, high tolerance to the presence of functional groups and exceptional high yields of Cu(I)-catalyzed 1,3-dipolar cycloadditions of azides with terminal alkynes (CuAAC) to give 1,4-disubstituted triazoles have made it a powerful approach for bioconjugation, construction and modification of materials and the parallel combinatorial synthesis of libraries of compounds for drug discovery. Recent efforts to further develop CuAAC have focused on one-pot multi-component reactions in which azides are prepared in-situ prior to the cycloaddition. The attraction of such an approach is that it minimizes time-consuming work-up and purification protocols and avoids handling of potentially explosive azides. Most methods for in-situ preparation of azides take advantage of the nucleophilicity of sodium azide towards electrophiles such as aromatic fluorides, iodides, benzylic bromides as well as epoxides and boronic acids. Organic azides have also been generated in-situ by Cu(II)-catalyzed diazo-transfer of triflyl azide or azidotrimethylsilane to amines. Surprisingly, one-pot multi-step reactions involving in-situ generation of terminal alkynes for click chemistry have not been reported. The attraction of such an approach is that a wide variety of alkynes can be generated from simple and readily available starting materials, such as aromatic halides.
Synthesis and Application of Glycopeptide and Glycoprotein Mimetics.
Herein, we describe a microwave-assisted one-pot three-step procedure entailing Sonogashira cross-coupling of aromatic halides with ethynyltrimethylsilane (TMS-acetylene) to give TMS-protected alkynes, which were desilylated and then employed in 1,3-dipolar cycloadditions with various azides to give a range of 1,2,3-triazoles (). In addition, it was found that the use of aromatic acyl chlorides in the Sonogashira cross-coupling gave TMS-protected ynones, which after desilylation and Cu(I)-catalyzed cycloadditions with azides led to the regioselective formation of 1-substituted 4-phenylacyl-1H-1,2,3-triazoles.
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