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

RSC Advances, Год журнала: 2021, Номер 11(6), С. 3452 - 3469

Опубликована: Янв. 1, 2021

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

Язык: Английский

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Modular Assembly of Six‐Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp³) Arylation Cascade

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(21), С. 2614 - 2620

Опубликована: Июль 3, 2024

Comprehensive Summary Concise assembly of spirooxindoles is great significance but a challenging task in modern organic synthesis. Described herein an unusual base‐promoted [4+2] spiroannulation rarely used isatin‐derived β‐silylcarbinols with o ‐halogen aromatic ketones, which enables rapid and modular synthesis six‐membered carbocyclic high yields excellent functional group tolerance (> 50 examples). Mechanistic experiments revealed that this reaction involved Peterson olefination, Michael addition intramolecular C(sp 3 ) arylation cascade. The variegated synthetic derivatization target products successful construction bioactive molecules further illustrate the potential spirooxindole‐related drug discovery.

Язык: Английский

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Domino Sonogashira coupling/metal carbene-involved annulation enabled by Pd/Cu relay catalysis: rapid assembly of indazole-containing biheteroaryls

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(9), С. 2171 - 2176

Опубликована: Янв. 1, 2023

An efficient and novel method has been developed for the synthesis of indazole-containing biheteroaryls via a domino Sonogashira coupling/azaenyne cycloisomerization/Barton–Kellogg reaction.

Язык: Английский

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Halocyclization of Olefinic 1,3-Dicarbonyls and Olefinic Amides in Aqueous Media Open in Air at Room Temperature

ACS Sustainable Chemistry & Engineering, Год журнала: 2020, Номер 8(45), С. 16946 - 16951

Опубликована: Ноя. 4, 2020

A green and efficient procedure for the preparation of valuable 2,3-dihydrofurans benzoxazines has been achieved through halocyclization olefinic 1,3-dicarbonyls or amides. This protocol could be conducted under catalyst-, base-, oxidant-free conditions in aqueous media open to air at room temperature with good excellent yields. Notably, practicality this method is further highlighted by gram-scale reactions

Язык: Английский

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Decade Advances of NaN₃ in Three‐component Reactions

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 10, 2023

Abstract Decade advances of sodium azide (2011–2022) have been summarized via mechanisms and target products. Sodium is commonly used as a nucleophile (N 3 − ) or radical source (⋅N in three‐component reactions. It's reactions with alkenes, alkynes, R−X (X=F, Cl, Br, I, OTs, B(OH) 2 , BF K, I + ArO Tf, N O SO ‐SiO other electrophiles will be discussed.

Язык: Английский

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Metal‐Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho‐Carbonyl Anilines

European Journal of Organic Chemistry, Год журнала: 2021, Номер 2021(29), С. 4125 - 4131

Опубликована: Июль 19, 2021

Abstract Here, we report a metal‐free synthesis of anthranils from ortho ‐carbonyl anilines using PhIO as sole additive under ambient conditions. This methodology did not require any external additives and delivered in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in‐situ generation iminoiodane leading to nitrene subsequent nucleophilic attack oxygen aniline on results heterocyclization.

Язык: Английский

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TfOH-Promoted Decyanative Cyclization toward the Synthesis of 2,1-Benzisoxazoles

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(11), С. 7326 - 7332

Опубликована: Май 20, 2021

A novel solvent-free, TfOH-promoted decyanative cyclization approach for the synthesis of 2,1-benzisoxazoles has been developed. The reactions are complete instantly at room temperature and result in formation desired a 34–97% isolated yield.

Язык: Английский

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Catalysed Aryl Amine Syntheses via Azides: From Azidation of Aryl Halides to Azide Reduction and Direct Amination

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Май 6, 2024

Abstract This review summarises and discusses aryl amine azide syntheses from halides employing azides. The majority of the reported reactions proceed with copper catalysis or mediation. Often, an is formed in first step, which then reduced situ to a second step. occurrence reduction, depends on chosen reaction conditions substrates. formation only azides through Cu‐mediated C−N bond formations discussed, followed by mediated catalytic reduction different systems, azidation amines, viz . azidation‐amination strategies. allows for synthesis complex heterocycles multi‐step one‐pot procedures, several are summarised here. Examples application synthesising important amines employed as biologically active compounds, materials science also summarised. Finally, conducted control have been collected discussed combination mechanistic proposals. literature survey us pinpoint design criteria valuable includes choice such solvent system additives, involved metal promising

Язык: Английский

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Sodium Azide: An Inorganic Nitrogen Source for the Synthesis of Organic N‐Compounds

ChemistrySelect, Год журнала: 2021, Номер 6(47), С. 13419 - 13433

Опубликована: Дек. 14, 2021

Abstract Sodium azide (NaN 3 ) is a colorless or white crystalline salt with diverse medicinal and industrial applications. Recently, NaN considered as an inexpensive valuable source of nitrogen in organic synthesis for the construction N ‐heterocycles, amines, nitriles amides due to extremely good nucleophilicity anion. Accordingly, can act single (a molecule transfer its azido group one atom) dual synthon (two molecules introduce two separate atoms, groups each) synthesis. However, although it has been extensively used there are rare reports on role synthon. In this review, we attempted summarize categorize recent literatures (from 2010 on) focusing use sodium usually via reductive amination brief concise description reaction mechanisms. respect, divided relevant database into main categories, namely The first category turn subcategories: (I) formation ‐heterocycles based number members rings (II) acyclic ‐compounds (primary amines/amides).

Язык: Английский

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Merging Ullmann-type cyclization and ring-expansion: a facile assembly of pyrimidine-fused quinazolinones by copper catalysis

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(8), С. 2002 - 2006

Опубликована: Янв. 1, 2023

A copper-catalyzed tandem cyclization reaction of readily available 4-bromoisatins and amidine hydrochlorides has been developed for the first time, enabling efficient synthesis pyrimidoquinazolinones in useful yields.

Язык: Английский

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