Literature DB >> 16465320

Regioselective functionalization of trisubstituted pyridines using a bromine-magnesium exchange.

Hongjun Ren1, Paul Knochel.   

Abstract

A tosyloxy substituent in position 2 allows a highly regioselective Br/Mg exchange reaction on 3,5-dibromopyridine derivatives using iso-PrMgCl.LiCl. The resulting functionalized pyridylmagnesium reagents react with various electrophiles in position 3. Acylated pyridines of this type can be readily converted into pyrazolo [3,4-b] pyridines.

Entities:  

Year:  2005        PMID： 16465320     DOI： 10.1039/b515168f

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


  3 in total

1.  A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 5: A Complete Set of Pyridine Boronic Acid Pinacol Esters Featuring Side Chains of Proteinogenic Amino Acids.

Authors:  Melanie Trobe; Till Schreiner; Martin Vareka; Sebastian Grimm; Bernhard Wölfl; Rolf Breinbauer
Journal:  European J Org Chem       Date:  2022-02-24

2.  Reliable Functionalization of 5,6-Fused Bicyclic N-Heterocycles Pyrazolopyrimidines and Imidazopyridazines via Zinc and Magnesium Organometallics.

Authors:  Saroj Kumar Rout; Agonist Kastrati; Harish Jangra; Kuno Schwärzer; Alisa S Sunagatullina; Maximilien Garny; Fabio Lima; Cara E Brocklehurst; Konstantin Karaghiosoff; Hendrik Zipse; Paul Knochel
Journal:  Chemistry       Date:  2022-05-11       Impact factor: 5.020

3.  Isothiourea-mediated one-pot synthesis of functionalized pyridines.

Authors:  Daniel G Stark; Louis C Morrill; Pei-Pei Yeh; Alexandra M Z Slawin; Timothy J C O'Riordan; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336
  3 in total

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