Five-Membered Ring Systems

Lopchuk, Justin M.

doi:10.1016/b978-0-08-100755-6.00006-5

Cited by 6 publications

(1 citation statement)

References 259 publications

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“…Pyrroles constitute one of the most important classes of heterocyclic compounds found in numerous natural products, pharmaceutical molecules, and functional materials . Indeed, pyrroles are precious scaffolds for pharmaceutical and medicinal research since they possess a broad spectrum of pharmacological and biological properties, including analgesic, antiallergic, anticonvulsant, antidepressant, antidiabetic, antihyperlipidemic, anti-inflammatory, antimicrobial, antifungal, antiviral, cholesterol-reducing, and antitumor properties .…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of 2-Acetyl-1H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

et al. 2021

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A one-pot two-step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic β-enaminones was described. When treated with zinc chloride in refluxing chloroform, N-propargylic β-enaminones produced in situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further refluxing in methanol with zinc chloride, afforded 2-acetyl-1H-pyrroles. The process was found to be general for a wide variety of N-propargylic β-enaminones and yielded a diverse range of 2-acetyl-1H-pyrroles in good to high yields with large substrate scope and good functional group tolerance. This operationally easy method may provide a rapid access to functionalized 2-acetyl-1H-pyrroles of pharmacological interest.

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Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of 2-Acetyl-1H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

et al. 2021

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Heterocycles from Cycloaddition of Alkynes

2022

Addition Reactions With Unsaturated Hydrocarbons

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A New Strategy for the Synthesis of 4‐Propargyl‐Substituted 1H‐Pyrroles fromN‐(5‐phenyl‐2,4‐pentadiynyl) β‐Enaminones

Yılmaz

Zora

2019

ChemistrySelect

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A new method for the synthesis of 4‐propargyl‐substituted 1H‐pyrroles is described. When treated with sodium hydride in refluxing dichloromethane, N‐(5‐phenyl‐2,4‐pentadiynyl) β‐enaminones, synthesized by the coupling of N‐propargylic β‐enaminones with phenylacetylene, afforded 4‐propargyl‐substituted pyrrole derivatives. This conversion was general for a variety of N‐(5‐phenyl‐2,4‐pentadiynyl) β‐enaminones and displayed broad functional group tolerance. During the reaction, not only cyclization of linear precursors to pyrrole ring takes place, but also propargyl group is introduced to pyrrole core in one‐pot. The enrichment of pyrrole compounds with a propargyl unit might exhibit potential for the synthesis of heterocyclic molecules of pharmacological interest.

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Five-Membered Ring Systems

Cited by 6 publications

References 259 publications

One-Pot Synthesis of 2-Acetyl-1H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

One-Pot Synthesis of 2-Acetyl-1H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

Heterocycles from Cycloaddition of Alkynes

A New Strategy for the Synthesis of 4‐Propargyl‐Substituted 1H‐Pyrroles fromN‐(5‐phenyl‐2,4‐pentadiynyl) β‐Enaminones

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