Organocatalyzed Synthesis of Functionalized Quinolines

Li, Lianhua; Niu, Zhi-Jie; Liang, Yong‐Min

doi:10.1002/asia.201901380

Cited by 32 publications

(5 citation statements)

References 88 publications

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“…[15,16] The conundrum is that homogeneous reactions usually entail tedious separation of catalyst residues, whereas the use of heterogeneous catalysts leads to undesired side reactions. [17,18] There is therefore a compelling need to develop SACs that enable efficient access to valuable quinoline derivatives with high selectivity and are easily separable from the reaction mixtures.…”

Section: Introductionmentioning

confidence: 99%

Iron Single Atom Catalyzed Quinoline Synthesis

Chen¹,

Song

Peng

et al. 2021

Advanced Materials

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has seen limited progress owing to their instability in solution and insufficient activation of reactants by single metal sites under ambient conditions. [4,5] Consequently, applications of SACs in organic synthesis were limited to certain hydrogenations, [6,7] oxidations, [8,9] and CC bond formations. [10] Very recently, we have reported the first SAC-catalyzed preparation of pharmaceuticals (Lonidamine etc., and their 15 N-labeled analogues) by selective hydrogenation to E-hydrazones and subsequent cyclization using Pt 1 /CeO 2 catalyst. [11] We have also developed the latestage functionalization of pharmaceuticals (Tamiflu) by chemoselective oxidation of sulfides using Co 1 -in-MoS 2 catalyst. [12] Despite excellent functional group tolerance and synthetic utility in both cases, the scope is limited by the use of complex starting materials (i.e., carboxylic esters mediated α-diazoesters synthesis and multifunctionalized sulfides), and the inaccessibility to synthesize multi-ring system as the reactions mainly involve simple hydrogenation/oxidation. [11,12] Quinolines, a major class of heterocycles, are widely occurring in natural and synthetic products with diverse pharmacological and physical properties. [13,14] Among the many methods to synthesize quinolines, the classical Friedländer condensation of an aromatic 2-amino-substituted carbonyl compound with another substituted carbonyl derivative is one of the simplest The production of high-value chemicals by single-atom catalysis is an attractive proposition for industry owing to its remarkable selectivity. Successful demonstrations to date are mostly based on gas-phase reactions, and reports on liquid-phase catalysis are relatively sparse owing to the insufficient activation of reactants by single-atom catalysts (SACs), as well as, their instability in solution. Here, mechanically strong, hierarchically porous carbon plates are developed for the immobilization of SACs to enhance catalytic activity and stability. The carbon-based SACs exhibit excellent activity and selectivity (≈68%) for the synthesis of substituted quinolines by a three-component oxidative cyclization, affording a wide assortment of quinolines (23 examples) from anilines and acetophenones feedstock in an efficient, atom-economical manner. Particularly, a Cavosonstat derivative can be synthesized through a one-step, Fe 1 -catalyzed cyclization instead of traditional Suzuki coupling. The strategy is also applicable to the deuteration of quinolines at the fourth position, which is challenging by conventional methods. The synthetic utility of the carbon-based SAC, together with its reusability and scalability, renders it promising for industrial scale catalysis.

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Section: Introductionmentioning

confidence: 99%

Iron Single Atom Catalyzed Quinoline Synthesis

Chen¹,

Song

Peng

et al. 2021

Advanced Materials

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“…This involves utilizing various catalysts such as transition metals, photocatalysts, and organo‐catalysts, which have demonstrated their efficacy in initiating desired reactions. Aniline, 2‐substituted aniline, and N ‐substituted aniline derivatives are commonly utilized as substrates [91,94–98] . In these substrates, aniline serves as a nitrogen‐carbon‐carbon (N−C−C) building block, 2‐substituted aniline functions as a nitrogen‐carbon‐carbon‐carbon (N−C−C−C) precursor, and N ‐substituted aniline acts as a carbon‐nitrogen‐carbon‐carbon (C−N−C−C) synthetic agent.…”

Section: Quinolinesmentioning

confidence: 99%

“…Aniline, 2-substituted aniline, and N-substituted aniline derivatives are commonly utilized as substrates. [91,[94][95][96][97][98] In these substrates, aniline serves as a nitrogen-carbon-carbon (NÀ CÀ C) building block, 2-substituted aniline functions as a nitrogen-carbon-carbon-carbon (NÀ CÀ CÀ C) precursor, and N-substituted aniline acts as a carbon-nitrogen-carbon-carbon (CÀ NÀ CÀ C) synthetic agent.…”

Section: Synthetic Strategies Of Quinolinementioning

confidence: 99%

Six‐Membered Aromatic Nitrogen Heterocyclic Anti‐Tumor Agents: Synthesis and Applications

Li,

Gu,

Nong

et al. 2023

The Chemical Record

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Cancer stands as a serious malady, posing substantial risks to human well‐being and survival. This underscores the paramount necessity to explore and investigate novel antitumor medications. Nitrogen‐containing compounds, especially those derived from natural sources, form a highly significant category of antitumor agents. Among these, antitumor agents with six‐membered aromatic nitrogen heterocycles have consistently attracted the attention of chemists and pharmacologists. Accordingly, we present a comprehensive summary of synthetic strategies and clinical implications of these compounds in this review. This entails an in‐depth analysis of synthesis pathways for pyridine, quinoline, pyrimidine, and quinazoline. Additionally, we explore the historical progression, targets, mechanisms of action, and clinical effectiveness of small molecule inhibitors possessing these structural features.

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“…16 a , b A comprehensive literature survey indicates that very few methods are available for obtaining molecules with quinone cores fused to quinoline or dihydroquinoline. These methods used syncarpic acid and rapanone as starting materials, which pose a significant challenge for synthesizing C-alkylation derivatives 17 (Scheme 1). In 2015, Nishimura et al reported the C-alkylation of syncarpic acids by Friedel–Crafts acylation of phloroglucinol, followed by tetra-methylation and reduction.…”

Section: Introductionmentioning

confidence: 99%