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

Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines DOI

Xiang Wang,

Huayou Hu,

Qiuyun Li

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 5, 2025

A base-promoted regioselective formal [3 + 2] annulation of pyridinium ylides with bromoalkynes is reported, producing a series substituent-diverse indolizines in generally good yields. mild K2CO3-promoted three-component cyclization and at 2:1 molar ratio delivered C2-acylmethylated indolizines, whereas C2-brominated were generated starting from bearing strong electron-withdrawing groups the unit by using 2,2,6,6-tetramethyl-1-piperidinyloxy as dehydrogenating reagent. The current synthetic methodology offers controllable modular approach to access different substitution patterns, featuring wide substrate scope, functional group compatibility, complete regioselectivity without demand any transition-metal catalysts.

Language: Английский

Citations

1
Synthesis of Highly Functionalized Indolizines via NIS-Promoted Spiroannulation/Ring-Opening Aromatization of Alkylidene Oxindoles with 2-(Pyridin-2-yl)acetate Derivatives DOI

Luan-Ting Wu,

Honglin Diao,

Yi Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

A novel NIS-promoted domino reaction of alkylidene oxindoles with 2-(pyridin-2-yl)acetate derivatives has been established, enabling the efficient and straightforward synthesis a vast variety highly functionalized indolizines via sequential spiroannulation ring-opening aromatization processes. The protocol features mild conditions, broad substrate scope, high efficiency, scalability, applicability for preparation CF3-containing indolizines. Furthermore, functional groups in indolizine framework provide feasibility follow-up derivatization. Based on mechanistic studies, plausible radical mechanism is proposed to elucidate formation

Language: Английский

Citations

0
Domino Approach to Heterocycles-Based Unsymmetrical Triarylmethanes through Heteroannulation of 2-(2-Enynyl)-pyridines with Enaminones DOI

Feroz Ahmad,

Pavit K. Ranga,

Shaheen Fatma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12104 - 12117

Published: Aug. 13, 2024

Herein, we report a copper-catalyzed protocol to access unsymmetrical triarylmethanes containing both indolizine and the chromone scaffolds in same molecule via 5-endo-dig cyclization of 2-(2-enynyl)-pyridines followed by reaction with 2-hydroxyaryl enaminones. A variety enaminones were subjected under optimal conditions, respective obtained good excellent yields.

Language: Английский

Citations

2
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