scholarly journals Site-selective Ru-catalyzed C–H bond alkenylation with biologically relevant isoindolinones: a case of catalyst performance controlled by subtle stereo-electronic effects of the weak directing group

2019 ◽  
Vol 9 (17) ◽  
pp. 4711-4717 ◽  
Author(s):  
Yu-Chao Yuan ◽  
Christian Bruneau ◽  
Thierry Roisnel ◽  
Rafael Gramage-Doria
Keyword(s):  
Electronic Effects ◽  
Biologically Relevant ◽  
Directing Group ◽  
Site Selective

A general regio- and site-selective ruthenium-catalyzed C–H bond alkenylation with the biologically relevant isoindolinone fragment serving as a weak directing group is presented.

scholarly journals The Programmed Multiple C–H Bond Functionalization of 4-Hydroxyquinoline and Its Medicinal Potential

2021 ◽  
Author(s):  
Quentin Ronzon ◽  
Wei Zhang ◽  
Nicolas Casaretto ◽  
Elizabeth Mouray ◽  
Isabelle Florent ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Multiple Site ◽  
Fries Rearrangement ◽  
Bond Functionalization ◽  
Chemical Libraries ◽  
Biologically Relevant ◽  
Directing Group ◽  
Metal Catalyzed ◽  
Site Selective

<p>The introduction of substituents on bare heterocyclic scaffolds can selectively be achieved by directed C–H functionalization. However, such methods have only occasionally been used, in an iterative manner, to decorate various positions of a medicinal scaffold to build chemical libraries. We herein report the multiple, site selective, metal-catalyzed C–H functionalization of a "programmed" 4-hydroxyquinoline. This medicinally privileged template indeed possesses multiple reactive sites for diversity-oriented functionalization, of which four were targeted. The C-2 and C-8 decorations were directed by an <i>N</i>-oxide, before taking benefit of an <i>O</i>-carbamoyl protection at C-4 to perform a Fries rearrangement and install a carboxamide at C-3. This also released the carbonyl group of 4-quinolones, the ultimate directing group to functionalize position 5. Our study highlights the power of multiple C–H functionalization to generate diversity in a biologically relevant library, after showing its strong antimalarial potential.</p>

scholarly journals Programmed multiple C–H bond functionalisation of the privileged 4-hydroxyquinoline template

2021 ◽  
Author(s):  
Quentin Ronzon ◽  
Wei Zhang ◽  
Nicolas Casaretto ◽  
Elizabeth Mouray ◽  
Isabelle Florent ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Multiple Site ◽  
Fries Rearrangement ◽  
Chemical Libraries ◽  
Biologically Relevant ◽  
Directing Group ◽  
Metal Catalyzed ◽  
Site Selective

<div> <p>The introduction of substituents on bare heterocyclic scaffolds can selectively be achieved by directed C–H functionalisation. However, such methods have only occasionally been used, in an iterative manner, to decorate various positions of a medicinal scaffold to build chemical libraries. We herein report the multiple, site selective, metal-catalyzed C–H functionalisation of a "programmed" 4-hydroxyquinoline. This medicinally privileged template indeed possesses multiple reactive sites for diversity-oriented functionalisation, of which four were targeted. The C-2 and C-8 decorations were directed by an <i>N</i>-oxide, before taking benefit of an O-carbamoyl protection at C-4 to perform a Fries rearrangement and install a carboxamide at C-3. This also released the carbonyl group of 4-quinolones, the ultimate directing group to functionalise position 5. Our study highlights the power of multiple C–H functionalisation to generate diversity in a biologically relevant library, after showing its strong antimalarial potential.</p></div>

scholarly journals Programmed multiple C–H bond functionalisation of the privileged 4-hydroxyquinoline template

2021 ◽  
Author(s):  
Quentin Ronzon ◽  
Wei Zhang ◽  
Nicolas Casaretto ◽  
Elizabeth Mouray ◽  
Isabelle Florent ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Multiple Site ◽  
Fries Rearrangement ◽  
Chemical Libraries ◽  
Biologically Relevant ◽  
Directing Group ◽  
Metal Catalyzed ◽  
Site Selective

<div> <p>The introduction of substituents on bare heterocyclic scaffolds can selectively be achieved by directed C–H functionalisation. However, such methods have only occasionally been used, in an iterative manner, to decorate various positions of a medicinal scaffold to build chemical libraries. We herein report the multiple, site selective, metal-catalyzed C–H functionalisation of a "programmed" 4-hydroxyquinoline. This medicinally privileged template indeed possesses multiple reactive sites for diversity-oriented functionalisation, of which four were targeted. The C-2 and C-8 decorations were directed by an <i>N</i>-oxide, before taking benefit of an O-carbamoyl protection at C-4 to perform a Fries rearrangement and install a carboxamide at C-3. This also released the carbonyl group of 4-quinolones, the ultimate directing group to functionalise position 5. Our study highlights the power of multiple C–H functionalisation to generate diversity in a biologically relevant library, after showing its strong antimalarial potential.</p></div>

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

Site-Selective Halogenation of Polyoxovanadate Clusters: Atomically Precise Models for Electronic Effects of Anion Doping in VO2

2019 ◽  
Vol 142 (2) ◽  
pp. 1049-1056 ◽  
Author(s):  
Brittney E. Petel ◽  
Rachel L. Meyer ◽  
Michela L. Maiola ◽  
William W. Brennessel ◽  
Astrid M. Müller ◽  
...  
Keyword(s):  
Electronic Effects ◽  
Anion Doping ◽  
Site Selective ◽  
Polyoxovanadate Clusters

scholarly journals A lesson for site-selective C–H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls

2018 ◽  
Vol 9 (1) ◽  
pp. 22-32 ◽  
Author(s):  
Koji Hirano ◽  
Masahiro Miura
Keyword(s):  
Pharmaceutical Chemistry ◽  
Recent Advances ◽  
Directing Group ◽  
Site Selective

This minireview focuses on recent advances in site-selective C–H functionalization on 2-pyridone which is an important heterocyclic motif in medicinal and pharmaceutical chemistry.

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