Synthesis of Quinoline Derivatives by Multicomponent Reaction Using Niobium Pentachloride as Lewis Acid

Andrade, Alexandre de Melo; Santos, Giovanny Carvalho dos; Silva‐Filho, Luiz Carlos da

doi:10.1002/jhet.1980

Cited by 27 publications

(7 citation statements)

References 58 publications

(56 reference statements)

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“…Consequently, many excellent catalytic systems such as AuCl 3 in methanol, Ph 3 PAuCl/AgOTf in THF and Au/TiO 2 were disclosed. In addition to Au‐catalysts, other homogeneous catalysts for example FeCl 3 , Fe(OTf) 3 , Yb(Pfb) 3 , YCl 3 , silver triflimide, Yb(OTf) 3 , Zn(OTf) 2 , NbCl 5 , triflic acid, Cu(OTf) 2 and molecular I 2 were also examined successfully. A large variety of aldehydes, alkynes and amines were screened to achieve quinolines under various conditions.…”

Section: Synthetic Utility Of A3 Coupling Reactionsmentioning

confidence: 99%

Recent Advances in the A³ Coupling Reactions and their Applications

2019

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Propargylamines are an important class of organic compounds that have been widely used as building blocks for the synthesis of various kinds of chemically and biologically relevant compounds. Over the last few years, there have been a rapid growth in the research dedicated to developing the synthetic protocol for propargylamine derivatives. Among various methods that are reported for the synthesis of propargylamines, the three‐component coupling of aldehyde, amine and alkyne (commonly termed as A3 coupling reactions) secured a special place because of its convenient/atom economical approach and thus broadly used by researchers. Our aim in this review is to highlight the most recent advancement on A3 coupling reactions for the synthesis of various propargylamine derivatives as well as on the developments of subsequent transformation of these compounds to useful heterocyclic compounds and the related products.

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Section: Synthetic Utility Of A3 Coupling Reactionsmentioning

confidence: 99%

Recent Advances in the A³ Coupling Reactions and their Applications

2019

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“…Brazil holds 86% of the world niobium reserves and this is one of the reasons why this metal became popular around here. Niobium(V) pentachloride has been employed as a very efficient Lewis acid in esterification reactions (de Sairre et al 2005, Aranda et al 2009, Diels-Alder (Constantino et al 2006), intramolecular Friedel-Crafts (Polo et al 2008), multicomponent reactions (de Andrade et al 2015) and others (Lacerda et al 2012) ( Figure 15).…”

Section: Catalysis By Metallic Speciesmentioning

confidence: 99%

Organic Synthesis: New Vistas in the Brazilian Landscape

Pilli

Assis

2018

An. Acad. Bras. Ciênc.

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In this overview, we present our analysis of the future of organic synthesis in Brazil, a highly innovative and strategic area of research which underpins our social and economical progress. Several different topics (automation, catalysis, green chemistry, scalability, methodological studies and total syntheses) were considered to hold promise for the future advance of chemical sciences in Brazil. In order to put it in perspective, contributions from Brazilian laboratories were selected by the citations received and importance for the field and were benchmarked against some of the most important results disclosed by authors worldwide. The picture that emerged reveals a thriving area of research, with new generations of well-trained and productive chemists engaged particularly in the areas of green chemistry and catalysis. In order to fulfill the promise of delivering more efficient and sustainable processes, an integration of the academic and industrial research agendas is to be expected. On the other hand, academic research in automation of chemical processes, a well established topic of investigation in industrial settings, has just recently began in Brazil and more academic laboratories are lining up to contribute. All these areas of research are expected to enable the future development of the almost unchartered field of scalability.

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“…Recently, our research group described the synthesis of quinoline derivatives through multicomponent reaction (MCR) between arylaldehydes, anilines and alkynes catalyzed by Niobium Pentachloride [71]. In this work, we describe the synthesis of nitroquinoline derivatives by MCRs, using the promoter NbCl 5 , followed by the reduction of nitro groups for obtaining the aminoquinoline derivatives.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Facile Synthesis and Photophysical Characterization of New Quinoline Dyes

et al. 2016

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This paper describes the synthesis of new quinoline derivatives, molecules that has been long interest in the organic and medicinal chemistry. Through the Multicomponent Reaction (MCR), an important tool in modern synthetic methodology, that generate products with good structural complexity, in addition to economy of atoms and selectivity, we provide easy access to the preparation of quinoline derivatives. The reactions were promoted by niobium pentachloride, as a Lewis acid. Subsequently, the synthesis of new aminoquinoline derivatives with good yields was performed using Pd/C and hydrazine. The photophysical investigations of quinoline derivatives show the substituent effect on the optical properties characterization was done by absorption and photoluminescence measurements with quantum yields of up to 83 %, the presence of the amino group at position 6 at the quinoline backbone was crucial for obtaining these increased quantum yields. Results show that these molecules may have potential use for a variety of applications and mainly attracts attention because of its wide potential of applicability in optoelectronic devices.

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Synthesis of Quinoline Derivatives by Multicomponent Reaction Using Niobium Pentachloride as Lewis Acid

Cited by 27 publications

References 58 publications

Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications

Organic Synthesis: New Vistas in the Brazilian Landscape

Facile Synthesis and Photophysical Characterization of New Quinoline Dyes

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Synthesis of Quinoline Derivatives by Multicomponent Reaction Using Niobium Pentachloride as Lewis Acid

Cited by 27 publications

References 58 publications

Recent Advances in the A3 Coupling Reactions and their Applications

Recent Advances in the A3 Coupling Reactions and their Applications

Organic Synthesis: New Vistas in the Brazilian Landscape

Facile Synthesis and Photophysical Characterization of New Quinoline Dyes

Contact Info

Product

Resources

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Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications