Literature DB >> 33890592

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

J R Alexander1, P V Kevorkian1, J J Topczewski1.   

Abstract

The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reaction is demonstrated on >15 examples with yields ranging from 37% to 86%.

Entities:  

Year:  2021        PMID： 33890592      PMCID： PMC8201930          DOI： 10.1039/d1cc01179k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  38 in total

1.  Pyrazolopyridinones as functionally selective GABAA ligands.

Authors:  Wesley P Blackaby; John R Atack; Frances Bromidge; Richard Lewis; Michael G N Russell; Alison Smith; Keith Wafford; Ruth M McKernan; Leslie J Street; José L Castro
Journal:  Bioorg Med Chem Lett       Date:  2005-11-15       Impact factor: 2.823

2.  Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.

Authors:  En-Chih Liu; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2019-03-21       Impact factor: 15.419

3.  Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition.

Authors:  Ute F Röhrig; Somi Reddy Majjigapu; Aurélien Grosdidier; Sylvian Bron; Vincent Stroobant; Luc Pilotte; Didier Colau; Pierre Vogel; Benoît J Van den Eynde; Vincent Zoete; Olivier Michielin
Journal:  J Med Chem       Date:  2012-05-22       Impact factor: 7.446

Review 4.  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

5.  Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3 + 2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions.

Authors:  David Amantini; Francesco Fringuelli; Oriana Piermatti; Ferdinando Pizzo; Ennio Zunino; Luigi Vaccaro
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

6.  Organic azides: an exploding diversity of a unique class of compounds.

Authors:  Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

Review 7.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622

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

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

Review 9.  Contribution of Organofluorine Compounds to Pharmaceuticals.

Authors:  Munenori Inoue; Yuji Sumii; Norio Shibata
Journal:  ACS Omega       Date:  2020-04-22

10.  4,5-Disubstituted 1,2,3-triazoles: Effective Inhibition of Indoleamine 2,3-Dioxygenase 1 Enzyme Regulates T cell Activity and Mitigates Tumor Growth.

Authors:  Subhankar Panda; Nirmalya Pradhan; Soumya Chatterjee; Sudhir Morla; Abhishek Saha; Ashalata Roy; Sachin Kumar; Arindam Bhattacharyya; Debasis Manna
Journal:  Sci Rep       Date:  2019-12-05       Impact factor: 4.379
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