Novel achievements with an old metal: copper-promoted synthesis of four-membered azacycles

Alcaide, Benito; Almendros, Pedro; Luna, Amparo

doi:10.1039/c3ra43861a

Cited by 19 publications

(6 citation statements)

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“…In addition to isoxazoline synthesis, nitrones are key precursors to diverse β-lactam structures through the copper(I)-catalyzed Kinugasa reaction with acetylides [ 7 , 8 ]. Since the initial report of the reaction between copper(I) acetylides and nitrones in pyridine in 1972 [ 8 ], the scope and limitations of the Kinugasa reaction have been explored by a number of research groups [ 9 , 10 , 11 ]. Recent progress in expanding the scope of the reaction has afforded the transition from requiring polar aprotic reaction media to an ‘on water’ approach, as well as employing detergents to allow for a micelle-promoted reaction to occur in aqueous medium [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

Kinugasa Reactions in Water: From Green Chemistry to Bioorthogonal Labelling

et al. 2015

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Abstract:The Kinugasa reaction has become an efficient method for the direct synthesis of β-lactams from substituted nitrones and copper(I) acetylides. In recent years, the reaction scope has been expanded to include the use of water as the solvent, and with micelle-promoted [3+2] cycloadditions followed by rearrangement furnishing high yields of β-lactams. The high yields of stable products under aqueous conditions render the modified Kinugasa reaction amenable to metabolic labelling and bioorthogonal applications. Herein, the development of methods for use of the Kinugasa reaction in aqueous media is reviewed, with emphasis on its potential use as a bioorthogonal coupling strategy.

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Section: Introductionmentioning

confidence: 99%

Kinugasa Reactions in Water: From Green Chemistry to Bioorthogonal Labelling

et al. 2015

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“…The unique ring tension and electronic structures of small ring (three-or four-membered ring) heterocyclic polymers may lead to intriguing properties and applications, where great potential exists. [4,49] However, restricted by ring tension as prementioned, in situ generation of small ring heterocyclic polymers are very rarely reported compared with those containing five or sixmembered rings.…”

Section: In Situ Generation Of Four-membered Ring Heterocyclic Polymersmentioning

confidence: 99%

In Situ Generation of Heterocyclic Polymers by Triple‐Bond Based Polymerizations

Wang

Han

Lam

et al. 2021

Macromol. Rapid Commun.

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Stemming from unique ring structures, heterocyclic polymers exhibit distinguished electrical, mechanical, and photophysical properties and have been widely used in a variety of important applications. Along with the technological significance are the challenges in their synthesis. Traditional synthetic strategies toward heterocyclic polymers often require the direct attachment of heterocycles to polymer backbones, which are generally limited by the lack of suitable and low-cost heterocyclic monomers, tedious reaction process, difficulties in incorporation of multiple substitutents, etc. Alternatively, in situ construction of heterocyclic polymers via triple-bond based polymerization offers promising prospects. This review summarized the recent progress on polymerizations of triple-bond based monomers including alkynes, nitriles, and isonitriles that can in situ generate heterocyclic polymers. The properties and advanced applications of the derived heterocyclic polymers will also be discussed. Finally, the future perspectives and challenges in this field will be addressed.

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“…The reaction proceeded in acetonitrile or DMF, on heating at 100 °C under microwave irradiation conditions. These conditions were initially chosen for attempted conversion of nitrone 52 into β‐lactams through the Kinugasa reaction . However, it appeared that the regioselectivity of the cycloaddition was opposite to that of a Kinugasa reaction, thus suggesting that activation of the alkyne by the copper salt failed.…”

Section: Experimental Conditions Inducing the Baldwin Rearrangementmentioning

confidence: 99%