Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 363(1), С. 2 - 39

Опубликована: Окт. 12, 2020

Abstract While remarkable progress has recently been made for the direct C−H‐functionalization of azines, its application is still limited by a lack accessible functional groups (primarily carbon‐based) and poor regioselectivity. In contrast, C2‐functionalized pyridines quinolines can be easily synthesized treating readily available N ‐oxides with various reagents under appropriate activation conditions. This review seeks to comprehensively document synthetic methods introducing at C2 position quinolines. this work, we highlight recent developments in C2‐functionalization pyridine quinoline address both mechanisms regioselectivity reactions. We also describe pathways reactive species involved these processes number medically relevant nitrogen heteroaromatics. magnified image

Язык: Английский

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Regioselective synthesis of 4-functionalized pyridines

Chem, Год журнала: 2023, Номер 10(2), С. 628 - 643

Опубликована: Ноя. 21, 2023

Язык: Английский

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Visible-Light-Driven Synergistic Se/Fe Catalysis for the Synthesis of 2-Aminoquinoline Derivatives

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 3, 2025

A visible-light-driven Se/Fe synergistic catalytic reaction between isocyanides and amines has been developed, employing air as the terminal oxidant. This efficient strategy offers facile access to 2-aminoquinoline scaffolds. The use of cost-effective readily available Fe(OTf)3 modulates selenium catalyst's oxidation state, enhancing method's environmental friendliness practicality. protocol is further distinguished by its good yields, broad substrate scope, mild conditions.

Язык: Английский

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Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate

Chinese Chemical Letters, Год журнала: 2021, Номер 32(11), С. 3518 - 3521

Опубликована: Май 7, 2021

Язык: Английский

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C2-Selective, Functional-Group-Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(7), С. 2885 - 2892

Опубликована: Фев. 9, 2022

Synthesis of heteroaryl amines has been an important topic in organic chemistry because their importance small-molecule discovery. In particular, 2-aminopyrimidines represent a highly privileged structural motif that is prevalent bioactive molecules, but general strategy to introduce the pyrimidine C2–N bonds via direct functionalization elusive. Here we describe synthetic platform for site-selective C–H affords pyrimidinyl iminium salt intermediates, which then can be transformed into various amine products situ. Mechanism-based reagent design allowed C2-selective amination pyrimidines, opening new scope functionalization. Our method compatible with broad range pyrimidines sensitive functional groups and access complex aminopyrimidines high selectivity.

Язык: Английский

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Lipid Trolling to Optimize A₃ Adenosine Receptor-Positive Allosteric Modulators (PAMs)

Journal of Medicinal Chemistry, Год журнала: 2024, Номер 67(14), С. 12221 - 12247

Опубликована: Июль 3, 2024

A

Язык: Английский

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Green and fast 2-aryloxylation/amination of quinolines

Green Chemistry, Год журнала: 2024, Номер 26(8), С. 4659 - 4664

Опубликована: Янв. 1, 2024

The direct C2-H functionalization of quinolines has always been a widely concerned area. Herein we report rapid and eco-friendly synthesis 2-aroxyquinolines 2-aminoquinolines through deoxygenative quinoline N -oxides.

Язык: Английский

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Phosphonium Salt-Promoted C2–H Functionalization of Heterocyclic N-Oxides

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9181 - 9185

Опубликована: Дек. 20, 2023

We report the development of a phosphonium salt as remarkable activating agent that enables direct conversion C2–H bonds variety heterocyclic N-oxides into C2–N, C2–O, or C2–S with high efficiency. The was prepared on >150 g scale in single step and is tolerant multiple functionalities.

Язык: Английский

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Selective SNH Alkylamination of 3(5,6,7,8)‐Nitroquinoline and 5‐Nitroisoquinoline in an Aqueous Medium

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 14, 2024

Abstract Direct oxidative S N H alkylamination of 3‐, 5‐, 6‐, 7‐, 8‐nitroquinolines and 5‐nitroisoquinoline in an aqueous solution aliphatic amines gives rise to the corresponding alkylamino dialkylamino derivatives these nitrohetarenes. The nitro group solely dictates regioselectivity reactions. antibacterial activity some them has been studied.

Язык: Английский

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Reaction of Pyridine‐N‐Oxides with Tertiary sp²‐N‐Nucleophiles: An Efficient Synthesis of Precursors for N‐(Pyrid‐2‐yl)‐Substituted N‐Heterocyclic Carbenes

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(24), С. 5777 - 5782

Опубликована: Окт. 15, 2020

Abstract N ‐(Pyrid‐2‐yl)‐substituted azolium and pyridinium salts, precursors for hybrid NHC‐containing ligands, were obtained with excellent regioselectivity, employing a deoxygenative CH‐functionalization of pyridine‐ ‐oxides substituted imidazoles, thiazoles, pyridine. Unlike the traditional S Ar‐based methods, this approach provides high yields substrates bearing substituents different electronic nature. The utility salts thus prepared was also highlighted by synthesis pyridyl‐substituted imidazolyl‐2‐thione, benzodiazepine as well 2‐aminopyridines. magnified image

Язык: Английский

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