Recent Progress in Catalytic Synthesis of 1,2,3-Triazoles

被引:41
作者
De Nino, Antonio [1 ]
Maiuolo, Loredana [1 ]
Costanzo, Paola [1 ]
Algieri, Vincenzo [1 ]
Jiritano, Antonio [1 ]
Olivito, Fabrizio [1 ]
Tallarida, Matteo Antonio [1 ]
机构
[1] Univ Calabria, Dipartimento Chim & Tecnol Chim, Via P Bucci,Cubo 12-C, I-87036 Arcavacata Di Rende, CS, Italy
关键词
1; 2; 3-triazoles; click chemistry; 3-dipolar cycloaddition; Huisgen reactions; triazole synthesis; AZIDE-ALKYNE CYCLOADDITION; METAL-FREE ROUTE; REGIOSELECTIVE SYNTHESIS; ONE-POT; 1,5-DISUBSTITUTED 1,2,3-TRIAZOLES; 1,3-DIPOLAR CYCLOADDITION; IONIC LIQUID; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; MULTICOMPONENT REACTION; BIOLOGICAL EVALUATION;
D O I
10.3390/catal11091120
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
1,2,3-triazoles represent a functional heterocyclic core that has been at the center of modern organic chemistry since the beginning of click chemistry. Being a versatile framework, such an aromatic ring can be observed in uncountable molecules useful in medicine and photochemistry, just to name a few. This review summarizes the progress achieved in their synthesis from 2015 to today, with particular emphasis on the development of new catalytic and eco-compatible approaches. In doing so, we subdivided the report based on their degree of functionalization and, for each subparagraph, we outlined the role of the catalyst employed.
引用
收藏
页数:48
相关论文
共 141 条
[11]   Enamine-Mediated Azide-Ketone [3+2] Cycloaddition of Azidoperfluoroalkanes [J].
Blastik, Zsofia E. ;
Klepetarova, Blanka ;
Beier, Petr .
CHEMISTRYSELECT, 2018, 3 (25) :7045-7048
[12]   Natural Deep Eutectic Solvent as Extraction Media for the Main Phenolic Compounds from Olive Oil Processing Wastes [J].
Bonacci, Sonia ;
Di Gioia, Maria Luisa ;
Costanzo, Paola ;
Maiuolo, Loredana ;
Tallarico, Sofia ;
Nardi, Monica .
ANTIOXIDANTS, 2020, 9 (06) :1-14
[13]   Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism [J].
Boren, Brant C. ;
Narayan, Sridhar ;
Rasmussen, Lars K. ;
Zhang, Li ;
Zhao, Haitao ;
Lin, Zhenyang ;
Jia, Guochen ;
Fokin, Valery V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8923-8930
[14]   The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition [J].
Breugst, Martin ;
Reissig, Hans-Ulrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (30) :12293-12307
[15]   I2/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines: Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions [J].
Cai, Zhong-Jian ;
Lu, Xin-Mou ;
Zi, You ;
Yang, Chao ;
Shen, Ling-Jie ;
Li, Jian ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
ORGANIC LETTERS, 2014, 16 (19) :5108-5111
[16]   A Presentation of Ionic Liquids as Lubricants: Some Critical Comments [J].
Calandra, Pietro ;
Szerb, Elisabeta I. ;
Lombardo, Domenico ;
Algieri, Vincenzo ;
De Nino, Antonio ;
Maiuolo, Loredana .
APPLIED SCIENCES-BASEL, 2021, 11 (12)
[17]   Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline [J].
Cao, Guorui ;
Yang, Kun ;
Li, Yue ;
Huang, Longjiang ;
Teng, Dawei .
MOLECULES, 2016, 21 (02)
[18]   Alkyl Propiolates Participated [3+2] Annulation for the Switchable Synthesis of 1,5-and 1,4-Disubstituted 1,2,3-Triazoles Containing Ester Side Chain [J].
Cao, Shuo ;
Liu, Yunyun ;
Hu, Changfeng ;
Wen, Chengping ;
Wan, Jie-Ping .
CHEMCATCHEM, 2018, 10 (21) :5021-5025
[19]   One-Pot, Three-Component Reaction Using Modified Julia Reagents: A Facile Synthesis of 4,5-Disubstituted 1,2,3-(NH)-Triazoles in a Wet Organic Solvent [J].
Chai, Huihui ;
Guo, Ruiqiang ;
Yin, Wei ;
Cheng, Lingping ;
Liu, Renhua ;
Chu, Changhu .
ACS COMBINATORIAL SCIENCE, 2015, 17 (03) :147-151
[20]   Synthesis of 1,4,5-trisubstituted triazoles by [3+2] cycloaddition of a ruthenium azido complex with ynoate esters [J].
Chang, Chao-Wan ;
Lee, Gene-Hsiang .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2019, 896 :146-153