Literature DB >> 35842885

A synthesis of functionalized 3-amino-1,2,4-triazoles from nitrile imines and guanidine derivatives.

Issa Yavari1, Zohreh Taheri2, Sara Sheikhi2.   

Abstract

A regioselective synthesis of trisubstituted 1,2,4-triazoles through reaction of nitrile imines with guanidine derivatives is described. These 1,3-dipolar cycloaddition reactions proceeded smoothly in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides fast access to a range of functionalized 3-amino-1,2,4-triazoles.
© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

Entities:  

Keywords:  Aminotriazole; Cyanoguanidine; Huisgen reaction; Nitrile imine; Tetramethylguanidine

Year:  2022        PMID： 35842885     DOI： 10.1007/s11030-022-10471-z

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   3.364


  13 in total

1.  Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones.

Authors:  Zeyang Wei; Qi Zhang; Meng Tang; Siyu Zhang; Qian Zhang
Journal:  Org Lett       Date:  2021-05-14       Impact factor: 6.005

2.  I2-Catalyzed Oxidative Coupling Reactions of Hydrazones and Amines and the Application in the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles.

Authors:  Zhengkai Chen; Hongli Li; Weipeng Dong; Maozhong Miao; Hongjun Ren
Journal:  Org Lett       Date:  2016-02-25       Impact factor: 6.005

Review 3.  The chemistry and biology of organic guanidine derivatives.

Authors:  Roberto G S Berlinck; Amaro E Trindade-Silva; Mario F C Santos
Journal:  Nat Prod Rep       Date:  2012-09-20       Impact factor: 13.423

4.  Development of a cell-based, high-throughput screening assay for ATM kinase inhibitors.

Authors:  Kexiao Guo; Anang A Shelat; R Kiplin Guy; Michael B Kastan
Journal:  J Biomol Screen       Date:  2014-01-24

5.  Recent development of synthetic preparation methods for guanidines via transition metal catalysis.

Authors:  Wen-Xiong Zhang; Ling Xu; Zhenfeng Xi
Journal:  Chem Commun (Camb)       Date:  2014-10-09       Impact factor: 6.222

6.  A Multicomponent Electrosynthesis of 1,5-Disubstituted and 1-Aryl 1,2,4-Triazoles.

Authors:  Na Yang; Gaoqing Yuan
Journal:  J Org Chem       Date:  2018-09-11       Impact factor: 4.354

7.  [3 + 2] Cycloaddition of Nitrile Ylides with Diazonium Salts: Copper-Catalyzed One-Pot Synthesis of Fully Substituted 1,2,4-Triazoles.

Authors:  Huihuang Li; Xueli Wu; Weiwei Hao; Haiyan Li; Yanwei Zhao; Yaxiong Wang; Pengcheng Lian; Yonggao Zheng; Xiaoguang Bao; Xiaobing Wan
Journal:  Org Lett       Date:  2018-08-27       Impact factor: 6.005

8.  Binding kinetics of ZM241385 derivatives at the human adenosine A2A receptor.

Authors:  Dong Guo; Lizi Xia; Jacobus P D van Veldhoven; Marc Hazeu; Tamara Mocking; Johannes Brussee; Adriaan P Ijzerman; Laura H Heitman
Journal:  ChemMedChem       Date:  2014-03-03       Impact factor: 3.466

9.  Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition-oxidative cyclization.

Authors:  Satoshi Ueda; Hideko Nagasawa
Journal:  J Am Chem Soc       Date:  2009-10-28       Impact factor: 15.419

10.  3-Dialkylamino-1,2,4-triazoles via ZnII-Catalyzed Acyl Hydrazide-Dialkylcyanamide Coupling.

Authors:  Sevilya N Yunusova; Dmitrii S Bolotin; Vitalii V Suslonov; Mikhail A Vovk; Peter M Tolstoy; Vadim Yu Kukushkin
Journal:  ACS Omega       Date:  2018-07-03
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