One-pot preparation of pyrrole derivatives via the copper-catalyzed [4+1] annulation of propargylic amines with ethyl glyoxylate and phenylglyoxal in the presence of piperidine

Sakai, Norio; Suzuki, Hiroki; Hori, Hiroaki; Ogiwara, Yohei

doi:10.1016/j.tetlet.2016.11.097

Cited by 8 publications

(3 citation statements)

References 47 publications

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“…Based on this transformation, they further developed a simplified version by employing ethyl glyoxylate and pyrrolidine as N,O-hemiacetal source, which could be converted to the corresponding pyrroles with propargylamines under the catalysis of copper(II) chloride. [55] However, both substrate scope and reaction yields were affected.…”

Section: Scheme 30 Rhodium and Silver-catalyzed Reaction Of Allylamines And Alkenesmentioning

confidence: 99%

Recent Advances on Pyrrole Synthesis through Different Annulation Modes

Xu¹,

Chen²,

Zhang³

et al. 2021

Chinese Journal of Organic Chemistry

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Section: Scheme 30 Rhodium and Silver-catalyzed Reaction Of Allylamines And Alkenesmentioning

confidence: 99%

Recent Advances on Pyrrole Synthesis through Different Annulation Modes

Xu¹,

Chen²,

Zhang³

et al. 2021

Chinese Journal of Organic Chemistry

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“…All reagents were purchased from Merck and used without additional purification. N-Propargyl-4-methylaniline was prepared (see scheme below) according to a previously reported procedure (Sakai et al, 2017). TLC aluminum sheets PF254 from Merck were employed to monitor the reaction progress.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine

et al. 2021

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The title heterocyclic compound, C20H27N, has been prepared in good yield (72%) via a BiCl3-catalyzed cationic Povarov reaction between N-propargyl-4-methylaniline and (±)-citronellal. The X-ray single-crystal study indicates that the structure consists of molecules connected by C—H...π contacts to produce chains, which pack in a sandwich–herringbone fashion along the b-axis direction. Hirshfeld surface analysis indicates that H...H interactions dominate by contributing 79.1% to the total surface. Energy frameworks and DFT calculations indicate a major contribution of dispersive forces to the total interaction energy.

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“…Besides DMAD, another alkyne reagent, the propargylic amine is also useful for the construction of a pyrrole ring. One‐pot preparation of pyrroles was achieved via copper (II)‐catalyzed [4+1] annulation of propargylic amines with N , O ‐acetals, or with alkyl/aryl glyoxylates [13,14]. In recent years, transition metal‐catalyzed reactions of 2‐diazoesters are successfully established to prepare pyrroles, such as the dual copper and dirhodium‐catalyzed reaction of tert‐ butyldimethylsilyl‐substituted vinyldiazoacetate with nitrones, copper‐catalyzed condensation of imines with α‐diazo‐β‐dicarbonyl compounds, copper(II)‐catalyzed reaction of enaminones with 2‐diazo‐2‐arylacetate, AgOTf‐catalyzed reaction of enaminones with aryl diazoesters, and rhodium(II)‐catalyzed intramolecular N─H insertion reactions of δ‐amino‐γ,γ‐difluoro‐α‐diazo‐β‐ketoesters [15–19].…”

Section: Introductionmentioning

confidence: 99%