Literature DB >> 32048510

Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases.

Kuno Schwärzer1, Carl Phillip Tüllmann1, Simon Graßl1, Bartosz Górski2, Cara E Brocklehurst3, Paul Knochel1.   

Abstract

We report the metalation of the 1,3,4-oxadiazole and 1,2,4-triazole scaffolds via regioselective zincation or magnesiation using the TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) TMP2Zn·2LiCl, TMP2Zn·2MgCl2·2LiCl, TMPMgCl·LiCl, and TMPZnCl·LiCl under mild conditions in THF. Subsequent trapping with various electrophiles including hydroxylamino benzoates gives access to functionalized heterocycles while tolerating many functional groups.

Entities:  

Year:  2020        PMID： 32048510     DOI： 10.1021/acs.orglett.0c00238

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


  5 in total

1.  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

2.  Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

Authors:  Alexander Kremsmair; Andreas Hess; Benjamin Heinz; Paul Knochel
Journal:  Chemistry       Date:  2021-11-29       Impact factor: 5.020

3.  A One-Pot Synthesis-Functionalization Strategy for Streamlined Access to 2,5-Disubstituted 1,3,4-Oxadiazoles from Carboxylic Acids.

Authors:  Daniel Matheau-Raven; Darren J Dixon
Journal:  J Org Chem       Date:  2022-09-02       Impact factor: 4.198

4.  Directed regioselective ortho,ortho'-magnesiations of aromatics and heterocycles using sBu2Mg in toluene.

Authors:  Andreas Hess; Jan P Prohaska; Sabrina B Doerrich; Florian Trauner; Ferdinand H Lutter; Sébastien Lemaire; Simon Wagschal; Konstantin Karaghiosoff; Paul Knochel
Journal:  Chem Sci       Date:  2021-05-18       Impact factor: 9.825

5.  Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg-Exchange Reaction Using sBu2 Mg in Toluene.

Authors:  Alisa S Sunagatullina; Ferdinand H Lutter; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-09       Impact factor: 16.823
  5 in total

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