Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

Fairoosa, Jaleel; Neetha, Mohan; Anilkumar, Gopinathan

doi:10.1039/d0ra10472h

Cited by 45 publications

(17 citation statements)

References 56 publications

(55 reference statements)

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“…The reliability, high efficiency, mild reaction conditions and wide scope of the substrate have led to its wide range of applications. [18] In order to find the best conditions for carrying out the one-pot three-component reaction leading to products 5, we first investigated the substitution reaction of 2-chloromethyl-3iodo-imidazo[1,2-a]pyridine 3 a with sodium azide. Different reaction parameters were examined for the optimization of this reaction step.…”

Section: Resultsmentioning

confidence: 99%

Cu/Pd‐Catalyzed One‐Pot Synthesis of 2‐(1,2,3‐Triazolyl)methyl‐3‐alkynylImidazo[1,2‐a]pyridines Involving Sequential SN Reaction/[3+2] Cycloaddition/Sonogashira Coupling Reactions

et al. 2021

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An efficient one-pot regioselective synthesis of 2-(1,2,3-triazolyl)methyl-3-alkynyl imidazo[1,2-a]pyridines is reported under simple and mild reaction conditions. The new imidazo[1,2-a] pyridines embedded with 4-substituted-[1,2,3]-triazole were obtained in good to excellent yields from 2-(chloromethyl)-3iodo imidazo[1,2-a]pyridines via a one-pot sequence involving an SN reaction with azide, followed by copper-catalyzed [3 + 2] cycloaddition and a Sonogashira coupling reaction.

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Section: Resultsmentioning

confidence: 99%

Cu/Pd‐Catalyzed One‐Pot Synthesis of 2‐(1,2,3‐Triazolyl)methyl‐3‐alkynylImidazo[1,2‐a]pyridines Involving Sequential SN Reaction/[3+2] Cycloaddition/Sonogashira Coupling Reactions

et al. 2021

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“…[37,38] In the presence of atmospheric oxygen, copper can change its oxidation state from + 2 to + 1 and reverse back to + 2, much more easily than zinc and cobalt. [22][23][24] As a result, the copper complex may produce more 4a than zinc and cobalt complexes. A detailed investigation of the redox mechanism of all these tested transition metals is part of our future work.…”

Section: Comparative Study Of 4' 5'-dinitro Anacardic Acid Copper(ii)...mentioning

confidence: 99%

Dinitro Anacardic Acid Copper(II) Complex—A Bio‐based Catalyst for Room Temperature Synthesis of Indolizine

Nagarkar

Dapurkar

2022

ChemistrySelect

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This article reports the room temperature, gram-scale synthesis of a novel, bio-based 4',5'-dintro anacardic acid copper(II) complex (2 : 1 form) and its application as a homogeneous catalyst for room temperature synthesis of 1,4-napthoquinone based indolizines. The bio-based 4',5'-dinitro anacardic acid copper(II) complex was derived from cashew nut shell liquid which is a renewable but underutilized agro by-product of the cashew industry. The synthesized copper complex was characterized through different techniques such as FT-IR, UV, ESI-MS, 1 H NMR, 13 C NMR, TGA, ICP-MPAES, and HPLC analysis. To evaluate catalyst performance, the synthesis of indolizine resulting from a three component reaction of 1, 4-naphthoquinone, pyridine, and ethyl acetoacetate was taken as a model reaction. Due to structural advantages, performance of the catalyst was excellent over the conventional copper salts in an array of green solvents. Further, the catalyst performance was tested using 3-substituted pyridines in model reaction and gave excellent regioselectivity. This article highlights the novel applications of naturally occurring anacardic acid and its copper derivatives in organic transformations.

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“…Multicomponent reactions (MCRs) are key transformations included in the modern synthetic chemistry toolbox since they allow rapid construction of diverse and complex libraries of bioactive compounds. Recent reviews on different types and aspects of MCRs exemplifies their prominence [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Among the most popular and studied types are, for example, the Ugi, Passerini, Biginelli, Hantzsch, and Mannich MCRs ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

In Melting Points We Trust: A Review on the Misguiding Characterization of Multicomponent Reactions Adducts and Intermediates

et al. 2022

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We discuss herein the problems associated with using melting points to characterize multicomponent reactions’ (MCRs) products and intermediates. Although surprising, it is not rare to find articles in which these MCRs final adducts (or their intermediates) are characterized solely by comparing melting points with those available from other reports. A brief survey among specialized articles highlights serious and obvious problems with this practice since, for instance, cases are found in which as many as 25 quite contrasting melting points have been attributed to the very same MCR adduct. Indeed, it seems logical to assume that the inherent non-confirmatory nature of melting points could be vastly misleading as a protocol for structural confirmation, but still many publications (also in the Q1 and Q2 quartiles) insist on using it. This procedure contradicts best practices in organic synthesis, and articles fraught with limitations and misleading conclusions have been published in the MCRs field. The drawbacks inherent to this practice are indeed serious and have misguided MCRs advances. We therefore suggest some precautions aimed at avoiding future confusions.

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Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

Abstract: Heterocycles are abundant in several pharmaceutical and naturally occurring compounds. Copper-catalyzed multicomponent reactions are a convenient method for easy access to heterocycles. In this review, we focus on the advancement in this field for the past two years.

Cited by 45 publications

References 56 publications

Cu/Pd‐Catalyzed One‐Pot Synthesis of 2‐(1,2,3‐Triazolyl)methyl‐3‐alkynylImidazo[1,2‐a]pyridines Involving Sequential SN Reaction/[3+2] Cycloaddition/Sonogashira Coupling Reactions

Cu/Pd‐Catalyzed One‐Pot Synthesis of 2‐(1,2,3‐Triazolyl)methyl‐3‐alkynylImidazo[1,2‐a]pyridines Involving Sequential SN Reaction/[3+2] Cycloaddition/Sonogashira Coupling Reactions

Dinitro Anacardic Acid Copper(II) Complex—A Bio‐based Catalyst for Room Temperature Synthesis of Indolizine

In Melting Points We Trust: A Review on the Misguiding Characterization of Multicomponent Reactions Adducts and Intermediates

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