Progress in the Chemistry of Tetrahydroquinolines

Chemical Reviews, Год журнала: 2019, Номер 119(8), С. 5057 - 5191

Опубликована: Апрель 9, 2019

Tetrahydroquinoline is one of the most important simple nitrogen heterocycles, being widespread in nature and present a broad variety pharmacologically active compounds. This Review summarizes progress achieved chemistry tetrahydroquinolines, with emphasis on their synthesis, during period from mid-2010 to early 2018.

Язык: Английский

---

Cu(I) Complexes Catalyzed the Dehydrogenation of N-Heterocycles

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4530 - 4537

Опубликована: Март 14, 2024

A copper-catalyzed method for the dehydrogenation of various nitrogen-containing heterocycles to furnish quinolines and indoles has been developed. range 1,2,3,4-tetrahydroquinolines underwent by employing 2 mol % copper complex Cat 3 as a catalyst using O2 an oxidant at 120 °C in 1,2-dichlorobenzene afford desired quinolines. The enables variety indolines presence 2, 10 TEMPO additive under room temperature tetrahydrofuran high yields. Mechanistic studies suggested that dehydrogenative activity is ascribed formation copper(II) active species from copper(I) complexes oxidized O2, which was proved high-resolution mass spectrometry (HRMS). reaction proceeds via superoxide radical anion (·O2–) electron paramagnetic resonance (EPR) spectrometry. In situ infrared spectroscopy revealed dihydroquinoline intermediate formed 1,2,3,4-tetrahydroquinolines.

Язык: Английский

---

Recent Progress in the Synthesis of Quinolines

Current Organic Synthesis, Год журнала: 2019, Номер 16(5), С. 671 - 708

Опубликована: Июль 23, 2019

Quinoline-containing compounds present in both natural and synthetic products are an important class of heterocyclic compounds. Many the substituted quinolines have been used various areas including medicine as drugs. Compounds with quinoline skeleton possess a wide range bioactivities such antimalarial, anti-bacterial, anthelmintic, anticonvulsant, antiviral, anti-inflammatory, analgesic activity. Due to applicability, synthesis derivatives has attracted lot attention chemists develop effective methods. known methods expanded improved. Furthermore, new for established. This review will focus on considerable studies date which back 2014.In this review, we discussed recent achievements Some classical modified improved, while other developed. A vast variety catalysts were these transformations. In some studies, reaction mechanisms also displayed.Many rings developed recently. Over past five years, majority those reported based cycloisomerization cyclization processes. Undoubtedly, more imaginative approaches appear literature near future. The application product is probably next challenge field.

Язык: Английский

---

A Comprehensive Investigation of Diverse Synthetic Methodologies for Constructing Quinoline Frameworks: A Critical Overview

ChemistrySelect, Год журнала: 2025, Номер 10(10)

Опубликована: Март 1, 2025

Abstract Recently, quinoline has emerged as a critical heterocyclic structure, attracting attention for its diverse industrial and synthetic organic chemistry applications. This compound is essential developing novel lead compounds in drug discovery extensively studied therapeutic derivatives medicinal chemistry. An extensive body of literature details the methodologies synthesizing this key scaffold functionalization to enhance biological efficacy. Numerous synthesis protocols have been documented, highlighting significance ongoing chemical research. These include various strategies, such transition metal‐catalyzed reactions environmentally sustainable processes, which are crucial constructing functionalizing derivatives. review aims systematically examine procedures findings, addressing limitations these pathways their environmental impacts. Additionally, curated selection quinolines will be presented.

Язык: Английский

---

Palladium-Catalyzed Cyclization of N-Acyl-o-alkynylanilines with Isocyanides Involving a 1,3-Acyl Migration: Rapid Access to Functionalized 2-Aminoquinolines

Organic Letters, Год журнала: 2018, Номер 20(22), С. 7245 - 7248

Опубликована: Ноя. 5, 2018

A simple and expedient approach for the synthesis of functionalized 2-aminoquinolines via palladium-catalyzed annulation N-acyl-o-alkynylanilines with isocyanides has been developed high atom economy, in which an unconventional 6-endo-dig cyclization process is observed. Further investigations mechanism demonstrated that intramolecular acyl migration N-protecting groups was involved this transformation.

Язык: Английский

---

Direct α-C–H amination using various amino agents by selective oxidative copper catalysis: a divergent access to functional quinolines

Chemical Communications, Год журнала: 2018, Номер 54(72), С. 10096 - 10099

Опубликована: Янв. 1, 2018

Herein, we present, for the first time, direct dehydrogenative α-C-H amination of tetrahydroquinolines (THQs) using various amino agents by selective aerobic copper catalysis, which enables divergent access to 2-aminoquinolines, core structures numerous functional products. In which, catalyst system preferentially oxidizes between two reactants, and presence TEMPO significantly enhances capability oxidation THQs makes it a kinetically controlled process, thus favoring C-N bond-forming step. The developed chemistry features broad substrates, excellent tolerance, high chemo-selectivity, no need pre-preparation specific aminating agents, offers practical way diverse atom-economic synthesis 2-aminoquinolines that are difficult prepare or inaccessible with existing C-H approaches.

Язык: Английский

---

A mild and metal-free synthesis of 2- and 1-alkyl/aryl/dialkyl-aminoquinolines and isoquinolines

RSC Advances, Год журнала: 2020, Номер 10(13), С. 7628 - 7634

Опубликована: Янв. 1, 2020

A simple synthetic strategy has been developed for the synthesis of 2- and 1-alkyl/aryl/dialkylaminoquinolines isoquinolines from easily available quinoline isoquinoline-N-oxides, different amines, triflic anhydride as activating agent acetonitrile solvent in a one-pot reaction under metal-free conditions at 0 °C to room temperature.

Язык: Английский

---

Site-Specific Oxidative C–H Chalcogenation of (Hetero)Aryl-Fused Cyclic Amines Enabled by Nanocobalt Oxides

Organic Letters, Год журнала: 2018, Номер 20(20), С. 6554 - 6558

Опубликована: Окт. 4, 2018

By employing reusable nanocobalt oxides as the catalysts, a site-specific oxidative C-H chalcogenation of (hetero)aryl-fused cyclic amines with various thiols and diselenides is presented for first time. The reaction proceeds selectively at sites (hetero)aryl rings para to N atom, enables access wide array chalcogenyl N-heteroarenes. merits transformation involve high step- atom-efficiency, excellent substrate functional compatibility, operational simplicity, use naturally abundant Co/O2 system. present work has offered fundamental basis selective synthesis N-heteroarenes from readily available feedstocks.

Язык: Английский

---

Inhibition of Yeast-to-Hypha Transition and Virulence of Candida albicans by 2-Alkylaminoquinoline Derivatives

Antimicrobial Agents and Chemotherapy, Год журнала: 2019, Номер 63(4)

Опубликована: Янв. 21, 2019

A rapid increase in Candida albicans infection and drug resistance has caused an emergent need for new clinical strategies against this fungal pathogen. In study, we evaluated the inhibitory activity of a series 2-alkylaminoquinoline derivatives C. isolates.

Язык: Английский

---

Silver-catalyzed direct C–H oxidative carbamoylation of quinolines with oxamic acids

Organic & Biomolecular Chemistry, Год журнала: 2020, Номер 18(14), С. 2747 - 2757

Опубликована: Янв. 1, 2020

A facile and highly efficient method has been successfully developed for the synthesis of 2-carbamoylated quinolines. The current reaction exhibits broad substrate scope, good functional group compatibility, to excellent yields.

Язык: Английский

---