Copper-mediated three-component synthesis of 3-cyanoimidazo[1,2-a]pyridines

Wen, Qiaodong; Lü, Ping; Wang, Yanguang

doi:10.1039/c5cc05821j

Cited by 49 publications

(16 citation statements)

References 58 publications

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“…Imidazo[1,2-a]pyridines are an important class of chemicals finding applications in the pharmaceutical industries as medicinally important compounds (See Figure 47). [58] Copper nitrate [Cu(NO 3 ) 2 .3H 2 O] effectively catalyzed cyanation of terminal alkynes using benzoyl cyanides as the "CN'' source under mild and aerobic conditions giving moderate to excellent catalytic performance for a broad range of aryl alkynes. Benzoyl cyanide was used as the non-toxic, facile and benign "CN'' source (See Figure 48).…”

Section: Benzyl Cyanidementioning

confidence: 99%

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Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

et al. 2021

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Earth‐abundant transition metal based catalytic materials can become pivotal for clean chemical manufacturing due to their facile handling and air moisture stability replacing conventional expensive noble metal based catalytic systems. Amongst the non‐noble metals, copper based catalytic systems due to the variable oxidation states have been effectively used as the tunable and multifunctional catalytic materials for the promotion of selective organic transformations. These copper based catalytic systems effectively promote multifarious organic transformations promoting functionalization of the easily available organic substrates. Nitriles are a significant class of nitrogen‐containing compounds finding applications in pharmaceutical and fine chemical industries. Several organic and inorganic cyanide sources have been effectively usedto cyanate organic compounds by using multi‐ferrous copper catalysts. Furthermore, nitrile compounds are key components used for the synthesis of drug molecules and fabrication of functionalized materials.

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Section: Benzyl Cyanidementioning

confidence: 99%

“…Imidazo[1,2‐ a ]pyridines are an important class of chemicals finding applications in the pharmaceutical industries as medicinally important compounds (See Figure 47). [58] …”

Section: Organic Cyanide Sourcementioning

confidence: 99%

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

et al. 2021

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“…Of late, many methods have been explored for the C‐3 functionalization of imidazo[1,2‐ a ]pyridines, viz . trifluoromethylation,9a sulfenylation,9b fluorination,9c cyanation,9d thiocyanation,9e dicarbonylation,9f aminomethylation9g as well as oxidative homocoupling of two imidazo[1,2‐ a ]pyridine moieties 9h. Although there have been significant developments toward the regioselective functionalization at the C‐3 carbon, the quest for further derivatizations is still ongoing.…”

Section: Introductionmentioning

confidence: 99%

N,N‐Dimethylacetamide (DMA) as a Methylene Synthon for Regioselective Linkage of Imidazo[1,2‐a]pyridine

2016

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Ac opper(II)-catalyzed oxidative methylene-bridged dimerizationo ft wo analogousi midazo[1,2-a]pyridines has been achieved using N,N-dimethylacetamide (DMA)a ss olvent cum methylene source.T hisr eactionw orks with av ariety of substituted imidazo[1,2-a]pyridines giving theirp roductsi n moderate to good yields. Isotopic labellinge xperiments revealed that the methylene group in the product originates from the N,N-dimethyl moiety of DMA.

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“…The theoretical study was carried out to check the feasibility of the reaction by calculating Gibbs free energy difference for each step (Scheme 42). The capability of copper to catalyze the cyanation reaction was well exploited by Wen and Lu for a one-pot MCR for the synthesis of cyanoimidazo[1,2- a ]pyridines 129 [128]. A variety of copper salts including CuI, CuBr, CuCl, Cu(OAc) 2 and Cu 2 O were tried but only CuI gave some appreciable results.…”

Section: Reviewmentioning

confidence: 99%

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

Reen

Kumar

Sharma

2019

Beilstein J. Org. Chem.

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A comprehensive account of recent advances in the synthesis of imidazopyridines, assisted through transition-metal-catalyzed multicomponent reactions, C–H activation/functionalization and coupling reactions are highlighted in this review article. The basic illustration of this review comprises of schemes with concise account of explanatory text. The schemes depict the reaction conditions along with a quick look into the mechanism involved to render a deep understanding of the catalytic role. At some instances optimizations of certain features have been illustrated through tables, i.e., selectivity of catalyst, loading of the catalyst and percentage yield with different substrates. Each of the reported examples has been rigorously analyzed for reacting substrates, reaction conditions and transition metals used as the catalyst. This review will be helpful to the chemists in understanding the challenges associated with the reported methods as well as the future possibilities, both in the choice of substrates and catalysts. This review would be quite appealing to a wider range of organic chemists in academia and industrial R&D sectors working in the field of heterocyclic syntheses. In a nutshell, this review will be a guiding torch to envisage: (i) the role of various transition metals in the domain dedicated towards method development and (ii) for the modifications needed thereof in the R&D sector.

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Copper-mediated three-component synthesis of 3-cyanoimidazo[1,2-a]pyridines

Cited by 49 publications

References 58 publications

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

N,N‐Dimethylacetamide (DMA) as a Methylene Synthon for Regioselective Linkage of Imidazo[1,2‐a]pyridine

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

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