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

Zefeng Jin,

Liejin Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(2), P. 252 - 268

Published: Nov. 28, 2023

Eight-membered heterocycles are important but their synthesis is usually challenging. This review summarizes the recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for assembling eight-membered heterocycles.

Language: Английский

Ag-Catalyzed Practical Synthesis of N-Acyl Anthranilic Acids from Anthranils and Carboxylic Acids DOI
Changshu Wu, Yang Gao, Yanping Huo

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3150 - 3160

Published: Feb. 9, 2024

A practical synthesis of valuable N-acyl anthranilic acids has been achieved via a silver-catalyzed imino-ketene generation from readily available anthranils and carboxylic acids. wide range including sterically demanding aliphatic acids, aromatic acrylic amino are compatible in this reaction. Moreover, method can be used to modify drug molecules natural products, such as ibuprofen, probenecid, acetylglycine.

Language: Английский

Citations

2
Diastereoselective synthesis of tetrahydrobenzo[b]azocines by Lu(OTf)3-catalyzed [4+4] cycloaddition of donor–acceptor cyclobutanes with anthranils DOI

Meifeng Hou,

Jiajun Li,

Fucai Rao

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(39), P. 5865 - 5868

Published: Jan. 1, 2022

A Lewis acid-catalyzed [4+4] cycloaddition reaction from D–A cyclobutanes and anthranils, providing the corresponding oxa-bridged eight-membered heterocycles under mild conditions.

Language: Английский

Citations

11
NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes with Anthranils DOI

Yushan Cui,

Yang Gao,

Wanxuan Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14861 - 14869

Published: Oct. 11, 2022

The regioselective hydroamination of unactivated alkenes is a long-standing challenge in organic synthesis. Herein, we report NiH-catalyzed proximal-selective with 8-aminoquinoline (AQ) as bidentate auxiliary and anthranils aminating reagents. A wide range primary aryl amines bearing an ortho-carbonyl group were installed both terminal internal alkenes, delivering variety valuable β- γ-amino acid building blocks, respectively, excellent regiocontrol. utility this transformation was further demonstrated by the conversion multifunctionalized into useful N-heterocycles.

Language: Английский

Citations

11
Interrupting the [Au]-Catalyzed Nitroalkyne Cycloisomerization: Trapping the Putative α-Oxo Gold Carbene with Benzo[c]isoxazole DOI
Pawan S. Dhote, Chepuri V. Ramana

Organic Letters, Journal Year: 2021, Volume and Issue: 23(7), P. 2632 - 2637

Published: March 19, 2021

The [Au]-catalyzed nitroalkyne cycloisomerization of 2-alkynylnitrobenzenes leading to anthranils has been interrupted by possible trapping the postulated intermediate α-oxo gold carbene with an external nucleophile such as benzo[c]isoxazole (anthranil). At outset, this provides a simple synthesis highly functionalized 3-acyl-(2-formylphenyl)-2H-indazoles sequential C–O, C–N, and N–N bond formations. This indirect support for existence carbenes in internal redox processes nitroalkynes.

Language: Английский

Citations

14
Recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for the synthesis of eight-membered heterocycles DOI
Yahui Wang,

Zefeng Jin,

Liejin Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(2), P. 252 - 268

Published: Nov. 28, 2023

Eight-membered heterocycles are important but their synthesis is usually challenging. This review summarizes the recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for assembling eight-membered heterocycles.

Language: Английский

Citations

5