Click chemistry -: What's in a name?: Triazole synthesis and beyond

被引:310
作者
Gil, Maria Victoria [1 ]
Arevalo, Maria Jose
Lopez, Oscar
机构
[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain
[2] Univ Seville, Fac Quim, Dept Quim Organ, E-41012 Seville, Spain
来源
SYNTHESIS-STUTTGART | 2007年 / 11卷 / 11期
关键词
drug research; supramolecular chemistry; Huisgen cycloadditions; triazole; aziridine opening; epoxide opening;
D O I
10.1055/s-2007-966071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The environmentally amiable route to carbon-heteroatorn bond formation, described by Sharpless as 'click chemistry', has become known as a fast, efficient, and reliable approach to the synthesis of novel compounds with desired functionalities. Readily available starting materials must be used in this methodology and they should be essentially inert to most biological and organic conditions, including water and molecular oxygen. In this review, we cover reactions included in this label such as cycloadditions, nucleophilic ring-opening reactions of strained cycles, and amide synthesis, as well as their applications in organic synthesis, molecular biology, macromolecular chemistry and materials science.
引用
收藏
页码:1589 / 1620
页数:32
相关论文
共 198 条
[1]   (-)-FR182877 is a potent and selective inhibitor of carboxylesterase-1 [J].
Adam, GC ;
Vanderwal, CD ;
Sorensen, EJ ;
Cravatt, BF .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5480-5484
[2]   A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].
Agard, NJ ;
Prescher, JA ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047
[3]   Mechanism of carbamate inactivation of FAAH: Implications for the design of covalent inhibitors and in vivo functional probes for enzymes [J].
Alexander, JP ;
Cravatt, BF .
CHEMISTRY & BIOLOGY, 2005, 12 (11) :1179-1187
[4]   A3-type star polymers via click chemistry [J].
Altintas, O. ;
Yankul, B. ;
Hizal, G. ;
Tunca, U. .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (21) :6458-6465
[5]   Bromolysis and iodolysis of α,β-epoxycarboxylic acids in water catalyzed by indium halides [J].
Amantini, D ;
Fringuelli, F ;
Pizzo, F ;
Vaccaro, L .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) :4463-4467
[6]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[7]  
ARCAMONE F, 1981, MED CHEM, V17, P1
[8]   Immobilization of biomaterials to nano-assembled films (self-assembled monolayers, Langmuir-Blodgett films, and layer-by-layer assemblies) and their related functions [J].
Ariga, Katsuhiko ;
Nakanishi, Takashi ;
Michinobu, Tsuyoshi .
JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY, 2006, 6 (08) :2278-2301
[9]   Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].
Bae, I ;
Han, H ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039
[10]   InBr3-catalyzed friedel-crafts addition of indoles to chiral aromatic epoxides:: A facile route to enantiopure indolyl derivatives [J].
Bandini, M ;
Cozzi, PG ;
Melchiorre, P ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5386-5389