A Rhodium‐Catalyzed Route for Oxidative Coupling and Cyclization of 2‐Aminobenzyl Alcohol with Ketones Leading to Quinolines.

Cho, Chan Sik; Seok, Hyo Jin; Shim, Sang Chul

doi:10.1002/chin.200604138

Cited by 3 publications

(3 citation statements)

References 4 publications

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“…In addition to RuCl 2 (DMSO) 4 , an indirect Friedländer process was reportedly promoted by iridium, palladium, copper, and rhodium complexes [ 46 , 47 , 48 , 49 , 50 , 51 ]. Figure 4 presents the common catalysts used in the annulation between aniline derivatives and hydroxylic scaffolds to achieve quinoline motifs.…”

Section: Chloroquine and Hydroxychloroquinementioning

confidence: 99%

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

2021

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The outbreak of SARS-CoV-2 has drastically changed our everyday life and the life of scientists from all over the world. In the last year, the scientific community has faced this worldwide threat using any tool available in order to find an effective response. The recent formulation, production, and ongoing administration of vaccines represent a starting point in the battle against SARS-CoV-2, but they cannot be the only aid available. In this regard, the use of drugs capable to mitigate and fight the virus is a crucial aspect of the pharmacological strategy. Among the plethora of approved drugs, a consistent element is a heterocyclic framework inside its skeleton. Heterocycles have played a pivotal role for decades in the pharmaceutical industry due to their high bioactivity derived from anticancer, antiviral, and anti-inflammatory capabilities. In this context, the development of new performing and sustainable synthetic strategies to obtain heterocyclic molecules has become a key focus of scientists. In this review, we present the recent trends in metal-promoted heterocyclization, and we focus our attention on the construction of heterocycles associated with the skeleton of drugs targeting SARS-CoV-2 coronavirus.

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Section: Chloroquine and Hydroxychloroquinementioning

confidence: 99%

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

2021

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“…In this process 2-aminobenzyl alcohol (75) initially undergoes oxidation to give oaminobenzaldehyde which subsequently undergoes cross aldol reaction with a wide variety of ketones (100) followed by dehydration to afford the corresponding quinolines (101) in moderate to good yields (Scheme 40). 69 Another modification of the Friedlander synthesis was reported by Taguchi et al, producing suitably substituted quinolines (101). In this protocol 2-aminobenzyl alcohol (75) undergoes reaction with 2equivalent of ketones (100) utilizing catalytic amount of [IrCl(cod) 2 ] or IrCl 3 and KOH without using any solvent (Scheme 41).…”

Section: Various Approaches For the Synthesis Of Quinolines And Theirmentioning

confidence: 99%

A review on transition-metal mediated synthesis of quinolines

2018

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Quinoline is one of the important class of heterocyclic compounds which have gained considerable importance because of its high pharmaceutical efficacy and broad range of biological activities such as anticancer, anti-malarial, anti-microbial and anti-asthmatic. As a consequence, the desire for new versatile and efficient route for the synthesis of quinoline scaffolds remains an active and growing area of interest both in academia and industry. However, developments of transition-metal catalyzed synthetic methods have witnessed a dominant position over the past few years for the synthesis of diverse range of complex heterocyclics containing quinoline scaffolds. This review specifically provides an overview of the literature available on the transitionmetal catalyzed synthetic methodologies for the synthesis of polysubstituted quinoline derivatives.

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“…In this regard, stable 2-aminobenzyl alcohols and abundant alcohols are applied to overcome the disadvantages of the classic Friedländer reaction in the presence of transition metal complexes. In the early stage, such processes have been well established using noble transition metal catalysts, such as Ru, 6 Rh, 7 Pd, 8 Ir, 9 and Re 10 complexes (Fig. 1b).…”

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confidence: 99%