Growing Impact of Intramolecular Click Chemistry in Organic Synthesis

被引:15
作者
Jaiswal, Manoj K. [1 ]
Tiwari, Vinod K. [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, India
关键词
Azides; Alkyne; Click Chemistry; CuAAC; RuAAC; Intramolecular Cyclization; Triazole; Regioselectivity; macrocyclization; AZIDE-ALKYNE CYCLOADDITION; DIVERSITY-ORIENTED SYNTHESIS; ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; AMINO-ACID; PEPTIDOMIMETIC MACROCYCLES; HUISGEN CYCLOADDITION; CYCLODEXTRIN ANALOGS; INSPIRED SYNTHESIS; FACILE SYNTHESIS;
D O I
10.1002/tcr.202300167
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Click Chemistry, a modular, rapid, and one of the most reliable tool for the regioselective 1,2,3-triazole forming [3+2] reaction of organic azide and terimal alkyne is widely explored in various emerging domains of research ranging from chemical biology to catalysis and medicinal chemistry to material science. This regioselective reaction from a diverse range of azido-alkyne scaffolds has been well performed in both intermolecular as well as intramolecular fashions. In comparison to the intermolecular metal (Cu/Ru/Ni) variant of 'Click Chemistry', the intramolecular click tool is little addressed. The intramolecular click chemistry is exemplified as a mordern tool of cyclization which involves metal-catalyzed (CuAAC/RuAAC) cyclization, organo-catalyzed cyclization, and thermal-induced topochemical reaction. Thus, we report herein the recent approaches on intramolecular azide-alkyne cycloaddition 'Click Chemistry' with their wide-spread emerging applications in the developement of a diverse range of molecules including fused-heterocycles, well-defined peptidomemics, and macrocyclic architectures of various notable features.
引用
收藏
页数:71
相关论文
共 237 条
[61]   Chemistry and Biology Of Multicomponent Reactions [J].
Domling, Alexander ;
Wang, Wei ;
Wang, Kan .
CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135
[62]  
Dörner S, 2005, CHEM COMMUN, P2852, DOI 10.1039/b502682b
[63]   The exploration of macrocycles for drug discovery - an underexploited structural class [J].
Driggers, Edward M. ;
Hale, Stephen P. ;
Lee, Jinbo ;
Terrett, Nicholas K. .
NATURE REVIEWS DRUG DISCOVERY, 2008, 7 (07) :608-624
[64]   Click inspired synthesis of triazole-linked vanillin glycoconjugates [J].
Dwivedi, Pratibha ;
Mishra, Kunj B. ;
Pritika ;
Mishra, Bhuwan B. ;
Tiwari, Vinod K. .
GLYCOCONJUGATE JOURNAL, 2017, 34 (01) :61-70
[65]   "Triazole Bridge": Disulfide-Bond Replacement by Ruthenium-Catalyzed Formation of 1,5-Disubstituted 1,2,3-Triazoles [J].
Empting, Martin ;
Avrutina, Olga ;
Meusinger, Reinhard ;
Fabritz, Sebastian ;
Reinwarth, Michael ;
Biesalski, Markus ;
Voigt, Stephan ;
Buntkowsky, Gerd ;
Kolmar, Harald .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) :5207-5211
[66]   Photoclick Chemistry: A Bright Idea [J].
Fairbanks, Benjamin D. ;
Macdougall, Laura J. ;
Mavila, Sudheendran ;
Sinha, Jasmine ;
Kirkpatrick, Bruce E. ;
Anseth, Kristi S. ;
Bowman, Christopher N. .
CHEMICAL REVIEWS, 2021, 121 (12) :6915-6990
[67]   Fused ring aziridines as a facile entry into triazole fused tricyclic and bicyclic heterocycles [J].
Fang, Fang ;
Vogel, Megan ;
Hines, Jennifer V. ;
Bergmeier, Stephen C. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (15) :3080-3091
[68]   A Hitchhiker's Guide to Click-Chemistry with Nucleic Acids [J].
Fantoni, Nicolo Zuin ;
El-Sagheer, Afaf H. ;
Brown, Tom .
CHEMICAL REVIEWS, 2021, 121 (12) :7122-7154
[69]   DNA-Encoded Chemistry: Drug Discovery from a Few Good Reactions [J].
Fitzgerald, Patrick R. ;
Paegel, Brian M. .
CHEMICAL REVIEWS, 2021, 121 (12) :7155-7177
[70]   Building blocks from monosaccharides for synthesis of scaffolds, including macrocycles. Application of allylic azide rearrangement, azide-alkyne cycloaddition and ring closing metathesis [J].
Fox, Karen A. ;
Chadda, Rekha ;
Cardona, Francisco ;
Barron, Stephen ;
McArdle, Patrick ;
Murphy, Paul, V .
TETRAHEDRON, 2020, 76 (45)