meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates

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Abstract: The functionalization of C−H bonds in heterocycles holds considerable importance in chemical synthesis and drug discovery. Recently, the regioselective introduction of various functionalities at the meta‐position of azines, utilizing readily accessible dearomatized intermediates, has emerged as a highly attractive approach. Along these lines, the meta‐hydroxylation of azines is an appealing but challenging transformation due to the inherent electronic nature of these heterocycles. Herein, we report a meta‐selective hydroxylation of pyridines, quinolines and isoquinolines through easily accessible oxazinoaza‐arene intermediates. The nucleophilic C3‐position of these dienamine‐type intermediates engages in highly regioselective hydroxylation upon treatment with electrophilic peroxides.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates ; day:19 ; month:02 ; year:2025 ; extent:7
Angewandte Chemie ; (19.02.2025) (gesamt 7)

Creator: Bhattacharya, Debkanta
Studer, Armido

DOI: 10.1002/ange.202423512

URN: urn:nbn:de:101:1-2502191323157.606127998761

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2002, 7:26 AM CEST

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Associated

Bhattacharya, Debkanta
Studer, Armido

Other Objects (12)

meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates

meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Catalytic hydroxylation in biphasic systems using CYP102A1 mutants

Catalytic hydroxylation in biphasic systems using CYP102A1 mutants

Electrochemical meta-C–H sulfonylation of pyridines with nucleophilic sulfinates

Electrochemical meta-C–H sulfonylation of pyridines with nucleophilic sulfinates

Organocatalytic C-H Hydroxylation

Organocatalytic C-H Hydroxylation

Selective Synthesis of Pyridines and Pyrimidines Using Isopropene Derivatives

Selective Synthesis of Pyridines and Pyrimidines Using Isopropene Derivatives

Denitrative Hydroxylation of Unactivated Nitroarenes **

Denitrative Hydroxylation of Unactivated Nitroarenes **

Chemoenzymatic Distal C–H Hydroxylation

Chemoenzymatic Distal C–H Hydroxylation

Decarboxylative Hydroxylation of Benzoic Acids

Decarboxylative Hydroxylation of Benzoic Acids

meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates

meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Catalytic hydroxylation in biphasic systems using CYP102A1 mutants

Catalytic hydroxylation in biphasic systems using CYP102A1 mutants

Electrochemical meta-C–H sulfonylation of pyridines with nucleophilic sulfinates

Electrochemical meta-C–H sulfonylation of pyridines with nucleophilic sulfinates

Organocatalytic C-H Hydroxylation

Organocatalytic C-H Hydroxylation

Selective Synthesis of Pyridines and Pyrimidines Using Isopropene Derivatives

Selective Synthesis of Pyridines and Pyrimidines Using Isopropene Derivatives

Denitrative Hydroxylation of Unactivated Nitroarenes **

Denitrative Hydroxylation of Unactivated Nitroarenes **

Chemoenzymatic Distal C–H Hydroxylation

Chemoenzymatic Distal C–H Hydroxylation

Decarboxylative Hydroxylation of Benzoic Acids

Decarboxylative Hydroxylation of Benzoic Acids

meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates

meta ‐Hydroxylation of Pyridines, Quinolines, and Isoquinolines Using Dearomatized Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Catalytic hydroxylation in biphasic systems using CYP102A1 mutants

Catalytic hydroxylation in biphasic systems using CYP102A1 mutants

Electrochemical meta-C–H sulfonylation of pyridines with nucleophilic sulfinates

Electrochemical meta-C–H sulfonylation of pyridines with nucleophilic sulfinates

Organocatalytic C-H Hydroxylation

Organocatalytic C-H Hydroxylation

Selective Synthesis of Pyridines and Pyrimidines Using Isopropene Derivatives

Selective Synthesis of Pyridines and Pyrimidines Using Isopropene Derivatives

Denitrative Hydroxylation of Unactivated Nitroarenes **

Denitrative Hydroxylation of Unactivated Nitroarenes **

Chemoenzymatic Distal C–H Hydroxylation

Chemoenzymatic Distal C–H Hydroxylation

Decarboxylative Hydroxylation of Benzoic Acids

Decarboxylative Hydroxylation of Benzoic Acids

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