Cited by Recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for the synthesis of eight-membered heterocycles

Copper‐Catalyzed Oxidative C─N Coupling of Carbazoles with Arylglyoxal Hydrates DOI

Lianji Zhang,

Dalong Pan,

Jinpeng Chu

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(19)

Published: May 1, 2025

Abstract In this study, a highly efficient Cu‐catalysed oxidative C─N coupling reaction was developed, which successfully achieved the of carbazole with aryl ketone aldehyde hydrates, showing wide range substrate applicability and good functional group tolerance. This method provides novel approach to synthesising diketones elucidates potential mechanism, thus offering significant tool for compounds demonstrating considerable application.

Language: Английский

Citations

Gold-Catalyzed Intermolecular Formal [4 + 2 + 2]-Cycloaddition of Anthranils with Allenamides DOI

Cheng Wang,

Guangyang Xu,

Ying Shao

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(15), P. 5990 - 5994

Published: July 17, 2020

The construction of eight-membered rings is a challenging issue due to unfavorable transannular strain and entropic barriers. We report herein gold-catalyzed formal [4 + 2 2] cycloaddition reaction anthranils with allenamides deliver oxa-bridged heterocycles in accepted yields unique E/Z configuration. Moreover, the asymmetric by using chiral phosphoramidite gold catalyst has also been conducted.

Language: Английский

Citations

Copper-Catalyzed Electrophilic Amination of Arylboronic Acids with Anthranils: An Access to N-Aryl-2-aminophenones DOI

Yang Gao, Simin Yang, Yibiao Li

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(15), P. 10222 - 10231

Published: July 7, 2020

An efficient copper-catalyzed electrophilic amination strategy has been established for the rapid synthesis of N-aryl-2-aminophenones from readily available arylboronic acids/esters and anthranils. This protocol features good functional group tolerance, broad substrate scope, operational simplicity. Moreover, a tandem C-H borylation C-N coupling also developed to transform simple arenes valuable in one pot. Additionally, synthetic potential this methodology is further demonstrated by various useful N-heterocycles derivatives.

Language: Английский

Citations

Cp*Co(iii)-catalyzed C–H amination/annulation cascade of sulfoxonium ylides with anthranils for the synthesis of indoloindolones DOI

Yogesh N. Aher, Amit B. Pawar

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(58), P. 7164 - 7167

Published: Jan. 1, 2021

An efficient synthesis of indoloindolones has been developed via [4+1] C–H amination/annulation cascade sulfoxonium ylides with anthranils using inexpensive and air stable [Cp*Co(CO)I₂] catalyst.

Language: Английский

Citations

Ru(ii) catalyzed chelation assisted C(sp²)–H bond functionalization along with concomitant (4 + 2) annulation DOI

Anindita Sarkar, Moumita Saha, Asish R. Das

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(27), P. 5567 - 5586

Published: Jan. 1, 2023

Efficacious protocols have been established to synthesize a structurally privileged Π-extended coumarin-fused pyridone nucleus by activating the vinylic C(sp2)-H bond of coumarin-3-carboxamide under influence inexpensive Ru(II)-metal. Here an N-methoxy carboxamide entity has exploited as chelating fragment manifest functionalization with concomitant (4 + 2) annulation reaction, resulting in heterocyclic ring-forming along sulfoxonium ylide and iodonium representative bench-stable carbene surrogates. This diverse heterocycle formation via insertion strategies, is further expanded activate ortho-C(sp2)-H bonds different heterocycles employing sp2-N moiety directing group develop acyl-alkylated/alkenylated quinazolines, isoxazoles highly fluorescent pyridone-N-oxides. Intriguingly, during evaluation versatility current protocols, one-pot double C-H activation rationalized presence ylide, which results biologically potent benzimidazole-fused coumarin-centered bridge-headed polycyclic heteroarenes. Furthermore, chemo-selective late-stage synthetic transformation being designed differently substituted analogues switching nature reducing agent. In addition, photophysical experiment was done on one pyridine-N-oxide compound (7e) delightfully it exhibited fluorescence quenching activity selectively Al3+ ions, appears be unique feature our methodology. Finally, upon correlation merit developed pathways, mediated strategy superior.

Language: Английский

Citations

Advances in transition metal-catalyzed C–H amination strategies using anthranils DOI

Yogesh N. Aher, Nilanjan Bhaduri, Amit B. Pawar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(44), P. 8794 - 8812

Published: Jan. 1, 2023

Modern times have witnessed an uprise in the synthesis and derivatization of nitrogen-containing fused heterocycles. Amination reactions involving nitrene chemistry always been most convenient choice for incorporation a nitrogen atom molecule. The utilization open species harnesses harsh conditions. Hence, transition metal-catalyzed C-H amination using aminating agents attractive choice. Electrophilic are well exploited due to their desirable reaction Out all, anthranils paved way forward utility simultaneously forming two new functional groups (amine carbonyl). follows metal-nitrenoid pathway. Often, has followed by Lewis acid or metal-mediated intramolecular cyclization directly produce This review broadly demonstrates as agent reactions. focus given scope, limitations, mechanistic understanding such electrophilic agent, anthranil, with metals.

Language: Английский

Citations

Copper-catalyzed C(sp)–H aryl amination enables modular synthesis of quinolines and 2-quinolinones DOI

Yang Gao, Haixia Li, Simin Yang

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 595 - 603

Published: Oct. 23, 2023

Language: Английский

Citations

Nickel-Catalyzed Hydroamination of Olefins with Anthranils DOI

Yang Gao,

Yushan Cui,

Yanping Huo

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(17), P. 12107 - 12118

Published: Aug. 24, 2021

A nickel-catalyzed polarity-reversed hydroamination of olefins has been achieved with anthranils as the electrophilic aminating agents and hydrosilane reductant. This protocol provides a facile access to N-alkyl-2-aminobenzophenones that are versatile intermediates in organic synthesis. wide range compatible this transformation, delivering desired amines useful excellent yields (38 examples, up 92% yield). The utility is exhibited late-stage functionalization drug molecules valuable derivatives obtained amination products.

Language: Английский

Citations

Practical synthesis of 3-aryl anthranils via an electrophilic aromatic substitution strategy DOI

Yang Gao, Simin Yang,

Minwei She

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(7), P. 2105 - 2114

Published: Jan. 1, 2022

A practical route for the synthesis of valuable 3-aryl anthranils from readily available and simple arenes has been achieved through an electrophilic substitution rearomatization sequence by employing Tf 2 O as effective activator.

Language: Английский

Citations

Copper‐catalyzed Reaction of Anthranils with Methyl Ketones: Site‐Selective C5‐Dicarbonylation of Anthranils DOI

Shi‐Yi Zhuang,

Yong‐Xing Tang,

Cai He

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 363(4), P. 1137 - 1141

Published: Dec. 18, 2020

Abstract A copper‐catalyzed site‐selective C5‐dicarbonylation reaction of anthranils has been developed for synthesis 1,2‐dicarbonyl compounds using methyl ketone as a commercially available carbonylation reagent. This process represents the first example to implement anthranils, which involves an oxidative C sp 3 ‐H/C 2 ‐H cross‐coupling along with thermolytic N−O bond cleavage. magnified image

Language: Английский

Citations