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Literature DB >> 18597477

Efficient synthesis of 2-substituted-1,2,3-triazoles.

Jarosław Kalisiak¹, K Barry Sharpless, Valery V Fokin.

Abstract

In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2 H-1,2,3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to N H-1,2,3-triazoles. The reaction is experimentally simple and readily scalable.

Entities: Chemical

Mesh：

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Year: 2008 PMID： 18597477 DOI： 10.1021/ol8006748

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

20 in total

1. Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.

Authors: Zhiwei Wen; Paloma R Tuttle; A Hasan Howlader; Anna Vasilyeva; Laura Gonzalez; Antonija Tangar; Ruipeng Lei; Eduardo E Laverde; Yuan Liu; Jaroslava Miksovska; Stanislaw F Wnuk
Journal: J Org Chem Date: 2019-03-06 Impact factor: 4.354

2. Azo-triazolide bis-cyclometalated Ir(iii) complexes via cyclization of 3-cyanodiarylformazanate ligands.

Authors: Ge Mu; Zhili Wen; Judy I-Chia Wu; Thomas S Teets
Journal: Dalton Trans Date: 2019-11-27 Impact factor: 4.390

3. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal.

Authors: Anwar Shamim; Frederico B Souza; Gustavo H G Trossini; Fernando M Gatti; Hélio A Stefani
Journal: Mol Divers Date: 2015-01-14 Impact factor: 2.943

Review 4. Strategies for Tuning the Selectivity of Chemical Probes that Target Serine Hydrolases.

Authors: Franco Faucher; John M Bennett; Matthew Bogyo; Scott Lovell
Journal: Cell Chem Biol Date: 2020-07-28 Impact factor: 8.116

5. Discovery and optimization of piperidyl-1,2,3-triazole ureas as potent, selective, and in vivo-active inhibitors of α/β-hydrolase domain containing 6 (ABHD6).

Authors: Ku-Lung Hsu; Katsunori Tsuboi; Jae Won Chang; Landon R Whitby; Anna E Speers; Holly Pugh; Benjamin F Cravatt
Journal: J Med Chem Date: 2013-10-23 Impact factor: 7.446

6. Development and optimization of piperidyl-1,2,3-triazole ureas as selective chemical probes of endocannabinoid biosynthesis.

Authors: Ku-Lung Hsu; Katsunori Tsuboi; Landon R Whitby; Anna E Speers; Holly Pugh; Jordon Inloes; Benjamin F Cravatt
Journal: J Med Chem Date: 2013-10-23 Impact factor: 7.446

Efficient synthesis of 2-substituted-1,2,3-triazoles.

1. Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.

2. Azo-triazolide bis-cyclometalated Ir(iii) complexes via cyclization of 3-cyanodiarylformazanate ligands.

3. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal.

Review 4. Strategies for Tuning the Selectivity of Chemical Probes that Target Serine Hydrolases.

5. Discovery and optimization of piperidyl-1,2,3-triazole ureas as potent, selective, and in vivo-active inhibitors of α/β-hydrolase domain containing 6 (ABHD6).

6. Development and optimization of piperidyl-1,2,3-triazole ureas as selective chemical probes of endocannabinoid biosynthesis.

7. Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.

8. New structural scaffolds for centrally acting oxime reactivators of phosphylated cholinesterases.

Review 9. Carbohydrate recognition by boronolectins, small molecules, and lectins.

10. Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.