Synthesis of benzenes from pyridines via N to C switch

Aífe Conboy; Michael f. Greaney

doi:10.1016/j.chempr.2024.05.004

Synthesis of benzenes from pyridines via N to C switch

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Abstract

The skeletal editing of hetero-arenes introduces new disconnections to the chemistry lexicon, enabling interconversion of ring systems via selective breaking / re-making of the carbon framework. We describe the one pot transformation of pyridines into benzene derivatives, using
a ring-opening / ring-closing (ANRORC) process with soft nucleophiles such as malonate. Triflic anhydride activates the pyridine to ANRORC synthesis via an isolable amine intermediate, which aromatizes on simple heating. The reaction has been exemplified with a room temperature protocol, along with direct syntheses of drug-like, tertiary-alkylated and isotopically-labelled benzoates.

Original language	English
Journal	Chem
Early online date	5 Jun 2024
DOIs	https://doi.org/10.1016/j.chempr.2024.05.004
Publication status	E-pub ahead of print - 5 Jun 2024

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10.1016/j.chempr.2024.05.004Licence: CC BY

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abstract = "The skeletal editing of hetero-arenes introduces new disconnections to the chemistry lexicon, enabling interconversion of ring systems via selective breaking / re-making of the carbon framework. We describe the one pot transformation of pyridines into benzene derivatives, using a ring-opening / ring-closing (ANRORC) process with soft nucleophiles such as malonate. Triflic anhydride activates the pyridine to ANRORC synthesis via an isolable amine intermediate, which aromatizes on simple heating. The reaction has been exemplified with a room temperature protocol, along with direct syntheses of drug-like, tertiary-alkylated and isotopically-labelled benzoates.",

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AU - Greaney, Michael f.

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AB - The skeletal editing of hetero-arenes introduces new disconnections to the chemistry lexicon, enabling interconversion of ring systems via selective breaking / re-making of the carbon framework. We describe the one pot transformation of pyridines into benzene derivatives, using a ring-opening / ring-closing (ANRORC) process with soft nucleophiles such as malonate. Triflic anhydride activates the pyridine to ANRORC synthesis via an isolable amine intermediate, which aromatizes on simple heating. The reaction has been exemplified with a room temperature protocol, along with direct syntheses of drug-like, tertiary-alkylated and isotopically-labelled benzoates.

U2 - 10.1016/j.chempr.2024.05.004

DO - 10.1016/j.chempr.2024.05.004

M3 - Article

SN - 2451-9294

JO - Chem

JF - Chem

ER -

Synthesis of benzenes from pyridines via N to C switch

Abstract

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