Literature DB >> 33797930

Silver Mediated Banert Cascade with Carbon Nucleophiles.

Juliana R Alexander1, Paul V Kevorkian1, Joseph J Topczewski1.   

Abstract

The Banert cascade of propargylic azides can be promoted by simple silver salts, and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. The Mayr nucleophilicity parameter (N) was found to correlate to the reaction efficiency, which enabled the formation of Csp3-Csp2 and Csp3-Csp3 bonds under otherwise identical conditions from structurally dissimilar nucleophiles.

Entities:  

Year:  2021        PMID： 33797930      PMCID： PMC8120647          DOI： 10.1021/acs.orglett.1c01032

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


  33 in total

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Authors:  Warren G Lewis; Luke G Green; Flavio Grynszpan; Zoran Radić; Paul R Carlier; Palmer Taylor; M G Finn; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-15       Impact factor: 15.336

Review 2.  Cu-catalyzed azide-alkyne cycloaddition.

Authors:  Morten Meldal; Christian Wenzel Tornøe
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

3.  Silver-Catalyzed Activation of Terminal Alkynes for Synthesizing Nitrogen-Containing Molecules.

Authors:  Paramasivam Sivaguru; Shanshan Cao; Kaki Raveendra Babu; Xihe Bi
Journal:  Acc Chem Res       Date:  2020-02-20       Impact factor: 22.384

Review 4.  Click chemistry in complex mixtures: bioorthogonal bioconjugation.

Authors:  Craig S McKay; M G Finn
Journal:  Chem Biol       Date:  2014-09-18

5.  Systematically Mitigating the p38α Activity of Triazole-based BET Inhibitors.

Authors:  Angela S Carlson; Huarui Cui; Anand Divakaran; Jorden A Johnson; Ryan M Brunner; William C K Pomerantz; Joseph J Topczewski
Journal:  ACS Med Chem Lett       Date:  2019-08-02       Impact factor: 4.345

Review 6.  Pharmacological significance of triazole scaffold.

Authors:  Rajeev Kharb; Prabodh Chander Sharma; Mohammed Shahar Yar
Journal:  J Enzyme Inhib Med Chem       Date:  2010-06-28       Impact factor: 5.051

7.  Nucleophilic reactivities of indoles.

Authors:  Sami Lakhdar; Martin Westermaier; François Terrier; Régis Goumont; Taoufik Boubaker; Armin R Ofial; Herbert Mayr
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

Review 8.  Medicinal attributes of 1,2,3-triazoles: Current developments.

Authors:  Divya Dheer; Virender Singh; Ravi Shankar
Journal:  Bioorg Chem       Date:  2017-01-18       Impact factor: 5.275

9.  Silver-catalysed reactions of alkynes: recent advances.

Authors:  Guichun Fang; Xihe Bi
Journal:  Chem Soc Rev       Date:  2015-07-29       Impact factor: 54.564

10.  Molecular Basis for the N-Terminal Bromodomain-and-Extra-Terminal-Family Selectivity of a Dual Kinase-Bromodomain Inhibitor.

Authors:  Anand Divakaran; Siva K Talluri; Alex M Ayoub; Neeraj K Mishra; Huarui Cui; John C Widen; Norbert Berndt; Jin-Yi Zhu; Angela S Carlson; Joseph J Topczewski; Ernst K Schonbrunn; Daniel A Harki; William C K Pomerantz
Journal:  J Med Chem       Date:  2018-10-16       Impact factor: 7.446
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  1 in total

1.  Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinated NH-1,2,3-triazoles.

Authors:  J R Alexander; P V Kevorkian; J J Topczewski
Journal:  Chem Commun (Camb)       Date:  2021-05-20       Impact factor: 6.222
  1 in total

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