Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides DOI
Feng Li, Qing Yang,

He Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11567 - 11575

Published: Aug. 1, 2024

An effective and straightforward Ag(I)-mediated annulation of 2-(2-enynyl)quinolines N'-(2-alkynylbenzylidene)hydrazides was developed, forging various synthetically challenging 17bH-isoquinolino[2'',1'':1′,6']pyridazino[4′,5′:3,4]pyrrolo[1,2-a]quinolines, including different nitrogen-containing fused rings, in moderate to excellent yields. This one-pot cycloaddition strategy features exclusive regioselectivity, high atom economy, broad substrate scope under mild conditions. The practicality reliability this reaction demonstrated by a successful scale-up synthesis.

Language: Английский

Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones DOI
Tao Zhou, Jing Zhou, Yunyun Liu

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 109683 - 109683

Published: March 2, 2024

Language: Английский

Citations

15
Nanocellulose as Convenient Reaction Media for the FeCl3 Mediated Mechanochemical Synthesis of 3-Acylchromones DOI Creative Commons
Satenik Mkrtchyan, Vishal B. Purohit, Viktor O. Iaroshenko

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 11(38), P. 13877 - 13884

Published: Sept. 11, 2023

A solvent free strategy for the mechanochemical synthesis of 3-acylchromones has been developed via FeCl3-nanocellulose mediated dehydrative coupling ortho-hydroxyarylenaminones and carboxylic acids. The undergo electrophilic domino cyclization followed by an unusual acylation event with acids in presence FeCl3 as catalyst nanocellulose reaction media. protocol was found to be simple, efficient, environmentally benign obtain a diverse array high yields. features advantages such use cheap readily available acyl source no requirement directing groups, oxidants, solvents. Furthermore, utilization wood-derived material, biodegradable media nontoxic iron salt under very mild solvent-free conditions makes this interesting perspective Green Chemistry principles.

Language: Английский

Citations

12
Base-Promoted Decarboxylative Annulation of Methyl 2-(2-Bromophenyl)acetates and Ynones to Access Benzoxepines DOI
Lulu Chen, Feng Li, Qing Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 3079 - 3088

Published: Feb. 17, 2023

A simple and efficient base-mediated decarboxylative annulation of ynones with methyl 2-(2-bromophenyl)acetates has been developed. broad range benzoxepines were prepared a substrate scope high regioselectivity in moderate to excellent yields under transition-metal-free conditions. This method proceeds through tandem [2 + 4] annulation, ring-opening reaction, the intramolecular nucleophilic aromatic substitution reaction. Additionally, key intermediates successfully obtained characterized unambiguously by single-crystal X-ray crystallography, which could favorably support mechanism. Furthermore, gram-scale reaction synthetic applications for further functionalization are also studied.

Language: Английский

Citations

4
Ag(I)-Mediated Annulation of 2-(2-Enynyl)pyridines and Propargyl Amines to Access 1-(2H-Pyrrol-3-yl)indolizines DOI
Feng Li, Qing Yang, Mingyue Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 304 - 312

Published: Dec. 21, 2023

An effective Ag(I)-mediated annulation of 2-(2-enynyl)pyridines and propargyl amines was developed, unexpectedly affording a broad range functionalized 1-(2H-pyrrol-3-yl)indolizines in moderate to excellent yields. The developed method is characterized by operational simplicity, ready availability starting materials, high regioselectivity, substrate scope under mild reaction conditions. Ag(I)-promoted cyclization possibly results the formation spiroindolizine, ring-opening rearrangement which may give 1-(2H-pyrrol-3-yl)indolizine. Furthermore, gram-scale synthetic transformations are also studied.

Language: Английский

Citations

4
HFIP promoted cyclization of o-hydroxyaryl enaminones with chlorohydrocarbon for synthesis of chromone-containing triarylmethanes DOI
Kai Yang,

Longhui Wu,

Xinlei Fu

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 156, P. 133948 - 133948

Published: March 16, 2024

Language: Английский

Citations

1
Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides DOI
Feng Li, Qing Yang,

He Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11567 - 11575

Published: Aug. 1, 2024

An effective and straightforward Ag(I)-mediated annulation of 2-(2-enynyl)quinolines N'-(2-alkynylbenzylidene)hydrazides was developed, forging various synthetically challenging 17bH-isoquinolino[2'',1'':1′,6']pyridazino[4′,5′:3,4]pyrrolo[1,2-a]quinolines, including different nitrogen-containing fused rings, in moderate to excellent yields. This one-pot cycloaddition strategy features exclusive regioselectivity, high atom economy, broad substrate scope under mild conditions. The practicality reliability this reaction demonstrated by a successful scale-up synthesis.

Language: Английский

Citations

0