Literature DB >> 20380424

Fused tetrazoles as azide surrogates in click reaction: efficient synthesis of N-heterocycle-substituted 1,2,3-triazoles.

Buddhadeb Chattopadhyay1, Claudia I Rivera Vera, Stepan Chuprakov, Vladimir Gevorgyan.   

Abstract

It has been shown that various pyrido-, quinolino-, pyrazino-, and quinoxalinotetrazoles can be used efficiently as azide components in Cu-catalyzed click reaction with alkynes. This method allows for efficient synthesis of a wide variety of N-heterocyclic derivatives of 1,2,3-triazoles.

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Year:  2010        PMID： 20380424      PMCID： PMC2862078          DOI： 10.1021/ol100745d

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


  18 in total

1.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

2.  A novel potent nicotinamide phosphoribosyltransferase inhibitor synthesized via click chemistry.

Authors:  Giampiero Colombano; Cristina Travelli; Ubaldina Galli; Antonio Caldarelli; Maria Giovanna Chini; Pier Luigi Canonico; Giovanni Sorba; Giuseppe Bifulco; Gian Cesare Tron; Armando A Genazzani
Journal:  J Med Chem       Date:  2010-01-28       Impact factor: 7.446

3.  Ruthenium-catalyzed cycloaddition of alkynes and organic azides.

Authors:  Li Zhang; Xinguo Chen; Peng Xue; Herman H Y Sun; Ian D Williams; K Barry Sharpless; Valery V Fokin; Guochen Jia
Journal:  J Am Chem Soc       Date:  2005-11-23       Impact factor: 15.419

4.  Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis.

Authors:  M J Genin; D A Allwine; D J Anderson; M R Barbachyn; D E Emmert; S A Garmon; D R Graber; K C Grega; J B Hester; D K Hutchinson; J Morris; R J Reischer; C W Ford; G E Zurenko; J C Hamel; R D Schaadt; D Stapert; B H Yagi
Journal:  J Med Chem       Date:  2000-03-09       Impact factor: 7.446

5.  Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.

Authors:  H M Davies; R J Townsend
Journal:  J Org Chem       Date:  2001-10-05       Impact factor: 4.354

6.  (1,2,3-Triazol-4-yl)benzenamines: synthesis and activity against VEGF receptors 1 and 2.

Authors:  Alexander S Kiselyov; Marina Semenova; Victor V Semenov
Journal:  Bioorg Med Chem Lett       Date:  2009-01-20       Impact factor: 2.823

7.  Copper-catalyzed azide-alkyne cycloaddition: regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles.

Authors:  Christian Spiteri; John E Moses
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

8.  Click chemistry beyond metal-catalyzed cycloaddition.

Authors:  C Remzi Becer; Richard Hoogenboom; Ulrich S Schubert
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Synthesis of 3-(1,2,3-triazol-1-yl)- and 3-(1,2,3-triazol-4-yl)-substituted pyrazolo[3,4-d]pyrimidin-4-amines via click chemistry: potential inhibitors of the Plasmodium falciparum PfPK7 protein kinase.

Authors:  Michael Klein; Peter Dinér; Dominique Dorin-Semblat; Christian Doerig; Morten Grøtli
Journal:  Org Biomol Chem       Date:  2009-07-02       Impact factor: 3.876

10.  1,2,3-Triazole-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D- ribofuranosyl]-3'-spiro-5"-(4"-amino-1",2"-oxathiole 2",2"-dioxide) (TSAO) analogues: synthesis and anti-HIV-1 activity.

Authors:  R Alvarez; S Velázquez; A San-Félix; S Aquaro; E De Clercq; C F Perno; A Karlsson; J Balzarini; M J Camarasa
Journal:  J Med Chem       Date:  1994-11-25       Impact factor: 7.446
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  3 in total

1.  Triazolbenzo[d]thiazoles: efficient synthesis and biological evaluation as neuroprotective agents.

Authors:  Belem Avila; Aaron Roth; Heather Streets; Donard S Dwyer; Mark J Kurth
Journal:  Bioorg Med Chem Lett       Date:  2012-07-20       Impact factor: 2.823

2.  Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions.

Authors:  Sajedeh Safapoor; Mohammad G Dekamin; Arezoo Akbari; M Reza Naimi-Jamal
Journal:  Sci Rep       Date:  2022-06-24       Impact factor: 4.996

3.  Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof.

Authors:  Laura Holzhauer; Chloé Liagre; Olaf Fuhr; Nicole Jung; Stefan Bräse
Journal:  Beilstein J Org Chem       Date:  2022-08-24       Impact factor: 2.544
  3 in total

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