Literature DB >> 15816729

Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles.

Steven J Coats1, Jeffrey S Link, Diane Gauthier, Dennis J Hlasta.   

Abstract

[reaction: see text] A regioselective method for the preparation of 1,5-trisubstituted 1H-1,2,3-triazoles via a 1,3-dipolar cycloaddition of 1-trimethylsilylacetylenes with organoazides is described. Immobilization of the azide on REM resin and subsequent cycloaddition afforded a 2 x 2 x 4 x 3 membered 1,5-disubstituted 1H-1,2,3-triazole library with an average purified yield of 68%.

Entities:  

Year:  2005        PMID： 15816729     DOI： 10.1021/ol047637y

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


  10 in total

1.  Glycosylated cell-penetrating peptides and their conjugates to a proapoptotic peptide: preparation by click chemistry and cell viability studies.

Authors:  Laurence Dutot; Pascaline Lécorché; Fabienne Burlina; Rodrigue Marquant; Vanessa Point; Sandrine Sagan; Gérard Chassaing; Jean-Maurice Mallet; Solange Lavielle
Journal:  J Chem Biol       Date:  2009-11-10

2.  Synthesis of purine modified 2'-C-methyl nucleosides as potential anti-HCV agents.

Authors:  Hong-wang Zhang; Longhu Zhou; Steven J Coats; Tamara R McBrayer; Phillip M Tharnish; Lavanya Bondada; Mervi Detorio; Sarah A Amichai; Melissa D Johns; Tony Whitaker; Raymond F Schinazi
Journal:  Bioorg Med Chem Lett       Date:  2011-09-20       Impact factor: 2.823

3.  A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes.

Authors:  Max M Majireck; Steven M Weinreb
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

4.  Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles.

Authors:  Sen W Kwok; Joseph R Fotsing; Rebecca J Fraser; Valentin O Rodionov; Valery V Fokin
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

5.  Iodine/palladium approaches to the synthesis of polyheterocyclic compounds.

Authors:  Saurabh Mehta; Richard C Larock
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

6.  Protein prosthesis: 1,5-disubstituted[1,2,3]triazoles as cis-peptide bond surrogates.

Authors:  Annie Tam; Ulrich Arnold; Matthew B Soellner; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2007-10-03       Impact factor: 15.419

7.  1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development.

Authors:  Grace H C Woo; Aaron B Beeler; John K Snyder
Journal:  Tetrahedron       Date:  2007-06-18       Impact factor: 2.457

8.  Preparation of ribavirin analogues by copper- and ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition.

Authors:  Ugo Pradere; Vincent Roy; Tamara R McBrayer; Raymond F Schinazi; Luigi A Agrofoglio
Journal:  Tetrahedron       Date:  2008-07-05       Impact factor: 2.457

9.  Parallel solid-phase synthesis of diaryltriazoles.

Authors:  Matthias Wrobel; Jeffrey Aubé; Burkhard König
Journal:  Beilstein J Org Chem       Date:  2012-07-06       Impact factor: 2.883

10.  Reactivity of ruthenium vinylidene complexes containing indenyl/dppe ligands and unsaturated bonds at Cδ with trimethylsilyl azide.

Authors:  Hui-Ling Sung; Tze-Min Her; Wen-Hsien Su; Chin-Pao Cheng
Journal:  Molecules       Date:  2012-07-17       Impact factor: 4.411
  10 in total

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