Oxime‐Derived Iminyl Radicals in Selective Processes of Hydrogen Atom Transfer and Addition to Carbon‐Carbon π‐Bonds

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(10), P. 2502 - 2528

Published: March 25, 2021

Abstract Oximes represent one of the fundamental organic compound classes with a wide range synthetic applications. In last decade O ‐substituted oximes were recognized as synthetically available and versatile precursors iminyl radicals via one‐electron oxidation or reduction employing visible light photoredox catalysts, salts abundant metals (such Cu Fe), other convenient reagents. Iminyl are powerful synthons for various processes cyclization, ring‐opening, CH‐functionalization, coupling. The present review is focused on methods based oxime‐derived developed in few years excluding ring opening reactions cyclic that summarized recent publications. consists two main parts: (1) involving 1,n‐hydrogen atom transfer (n=5 most cases) (2) addition radical to carbon‐carbon π‐bond. magnified image

Language: Английский

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Well-Defined Phosphine-Free Manganese(II)-Complex-Catalyzed Synthesis of Quinolines, Pyrroles, and Pyridines

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(13), P. 8351 - 8367

Published: June 21, 2022

Herein, we report a simple, phosphine-free, and inexpensive catalytic system based on manganese(II) complex for synthesizing different important N-heterocycles such as quinolines, pyrroles, pyridines from amino alcohols ketones. Several control experiments, kinetic studies, DFT calculations were carried out to support the plausible reaction mechanism. We also detected two potential intermediates in cycle using ESI-MS analysis. Based these metal-ligand cooperative mechanism was proposed.

Language: Английский

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Amine Functionalized Pincer-like Azo-aromatic Complexes of Cobalt and Their Catalytic Activities in the Synthesis of Quinoline via Acceptorless Dehydrogenation of Alcohols

Organometallics, Journal Year: 2023, Volume and Issue: 42(15), P. 1854 - 1868

Published: July 6, 2023

Herein we disclose a series of phosphine-free cobalt(II)-based catalytic systems bearing redox non-innocent amine functionalized azo-aromatic pincer-like ligand for the synthesis quinoline by dehydrogenative oxidation 2-amino benzyl alcohol and subsequent coupling with ketone. All precatalysts were characterized thoroughly using various spectroscopic techniques DFT studies. The protocol was efficient versatile, providing major advances in quinoline. It also found to be applicable gram-scale quinolines as well. Several control experiments, kinetic studies, studies have proposed plausible reaction mechanism where azo-pyridine moiety acts activate α-C–H bond Co(II) → Co(I) reduction leads formation aldehyde. generated aldehyde undergoes base-catalyzed C–C result quinolines. potential controls efficiency precatalysts. Thus, complex 3 most anodic best precatalyst among complexes 1–4.

Language: Английский

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Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2142 - 2164

Published: Jan. 17, 2024

Abstract N‐Heterocyclic compounds, in particular, quinolines and quinazolines are frequently used medicinal chemistry. Therefore, the direct clean synthesis of these valuable scaffolds has been a great interest for many years. 2‐Aminobenzyl alcohols as an alternative reactant instead unstable expensive 2‐aminobenzaldehydes can be construction N‐fused heterocycles including quinolines, quinazolines, oxazines, thiazines, selenazines, imidazoles, diazepines, etc. In this review article, we have discussed recent developments use 2‐aminobenzyl diverse heterocycles.

Language: Английский

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Access to 4-Trifluoromethyl Quinolines via Cu-Catalyzed Annulation Reaction of Ketone Oxime Acetates with ortho-Trifluoroacetyl Anilines under Redox-Neutral Conditions

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(9), P. 5804 - 5816

Published: April 27, 2022

An efficient Cu-catalyzed annulation reaction of ketone oxime acetates with ortho-trifluoroacetyl anilines has been disclosed. With the developed protocol, a series 4-trifluoromethyl quinolines were obtained in good to excellent yields (58-99%) under redox-neutral conditions. The protocol also could be extended ferrocene-based for construction ferrocene-substituted fluorine-containing quinolines.

Language: Английский

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Construction of effective and recyclable non-precious metal coordination polymers and their multiple applications in water

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111165 - 111165

Published: April 1, 2025

Language: Английский

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Iodine‐Promoted Synthesis of Dipyrazolo/Diuracil‐Fused Pyridines and o‐Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4‐Methylazaarenes

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(19), P. 4632 - 4638

Published: Aug. 24, 2021

Abstract The iodine‐promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biologically important azaarene‐substituted bis‐pyrazolo[3,4‐ b :4′,3′‐ e ]pyridines (BPPs), diuracilpyridines o ‐amino diheteroaryl ketones. procedure proceeded with easily available methyl azaarenes, 5‐aminouracils substituted 5‐aminopyrazoles. This protocol is a simple metal‐free approach which exhibits high functional group compatibility broad substrates scope. Moreover, this transformation can be applied preparation dipyrazolo/diuracil‐fused pyridines on gram scale. magnified image

Language: Английский

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Potent pincer-zinc catalyzed homogeneous α-alkylation and Friedländer quinoline synthesis reaction of secondary alcohols/ketones with primary alcohols

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6393 - 6408

Published: Jan. 1, 2024

Herein, we describe an air- and moisture-stable, homogeneous zinc catalyst stabilised using electron deficient N^N^N pincer-type ligand.

Language: Английский

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Recent Advances in Green Synthesis of Functionalized Quinolines of Medicinal Impact (2018‐Present)

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(40)

Published: Oct. 25, 2022

Abstract The synthetic chemists are awakening to make substantial development in finding safer drugs against the rising communicable and non‐communicable type of diseases. By replacing traditional methods more sustainable greener approaches, multicomponent reactions rapid efficient tool for synthesis organic molecules structural diversity complexity. Heterocyclic chemistry transforms small set precursors into series by domino reactions. This review covers recent trends last five years (2018–2022) construction potentially drug‐like quinoline derivatives. discussed here preferable over conventional approaches being inexpensive, consuming lesser reaction time, atom economical, saving energy manpower while avoiding toxic reagents/materials, chemical wastes environmental/occupational benign. contributions covered involve metallic, metal free strategies other catalytic pathways including nanoparticles, ionic liquids photocatalysis which operationally safe reliable.

Language: Английский

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Acid/base-co-catalyzed cyclization of ketones with o-amino-benzylamines: Direct synthesis of quinoline compounds

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 128, P. 154700 - 154700

Published: Aug. 10, 2023

Language: Английский

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