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

Pd/Cu-Catalyzed Synthesis of Internal and Sila-Ynones by Direct Selective Acyl Sonogashira Cross-Coupling of Carboxylic Acids with Terminal Alkynes DOI
Xue Liu, Xinyi Li, Long Liu

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(9), P. 5819 - 5827

Published: April 13, 2023

The direct acyl Sonogashira cross-coupling of carboxylic acids with terminal alkynes has been achieved through Pd/Cu cooperative catalysis. In this reaction, the readily available act as source for coupling various to produce highly valuable ynones in good high yields. reaction features chemoselectivity and functional group tolerance. offers access versatile silyl-ynones. late-stage modification bioactive molecules gram-scale experiments highlight synthetic value organic synthesis. method enables preparation directly from absence C(acyl)–C(sp) decarbonylation.

Language: Английский

Citations

18
A photoredox- or metal-catalyzed three-component cyanoalkylsulfonylation reaction of 1-(allyloxy)-2-(1-arylvinyl)benzenes, potassium metabisulfite, and cycloketone oxime esters: synthesis of cyanoalkylsulfonylated benzoxepines DOI
Nengneng Zhou,

Sixin Wu,

Kaimo Kuang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(21), P. 6032 - 6037

Published: Jan. 1, 2021

A visible light photocatalyzed or metal-catalyzed three-component cyanoalkylsulfonylation of 1-(allyloxy)-2-(1-arylvinyl)benzenes, potassium metabisulfite and cyclobutanone oxime esters is developed.

Language: Английский

Citations

35
Synthesis of 3-(2-quinolyl) chromones from ynones and quinolineN-oxidesviatandem reactions under transition metal- and additive-free conditions DOI
Jing Liu,

Dan Ba,

Yanhui Chen

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(29), P. 4078 - 4081

Published: Jan. 1, 2020

A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- additive-free conditions can be amplified to gram level in 91% yield. 3-(1-Isoquinolyl) 3-(2-pyridyl) are also successfully synthesized using isoquinoline pyridine basic conditions. Various heteroarene-contaning were afforded 30-98% yields, which difficult obtained compounds interest pharmaceutical chemistry chemical biology.

Language: Английский

Citations

27
Recent trends for chemoselectivity modulation in one-pot organic transformations DOI Creative Commons

Hiren R. Chaudhary,

Divyang M. Patel

RSC Advances, Journal Year: 2024, Volume and Issue: 14(42), P. 31072 - 31116

Published: Jan. 1, 2024

This article describes recent advances in one-pot chemoselective reactions and their mechanism insights. Here, the substrate, catalyst, solvent, temperature play a vital role modulating chemoselectivity.

Language: Английский

Citations

3
Palladium-catalyzed ionic liquids-mediated cascade carbonylative alkynylation of diaryl ethers with alkynes DOI Creative Commons
Jianxiao Li, Qianfan Yang, Youmao Qi

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0
Solvent-controlled divergent annulation of ynones and (iso)quinoline N-oxides: of 3-((iso)quinolin-1-yl)-4H-chromen-4-ones and 13H-isoquinolino[2,1-a]quinolin-13-ones DOI

Wan-Wan Yang,

Lulu Chen, Pei‐Jer Chen

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 56(8), P. 1183 - 1186

Published: Dec. 16, 2019

An effective annulation of ynones and (iso)quinoline N-oxides was developed to divergently prepare 3-((iso)quinolin-1-yl)-4H-chromen-4-ones 13H-isoquinolino[2,1-a]quinolin-13-ones under transition-metal-free conditions.

Language: Английский

Citations

23
An efficient tandem synthesis of chromones from o-bromoaryl ynones and benzaldehyde oxime DOI
Jingwen Zhang,

Wan-Wan Yang,

Lulu Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(32), P. 7461 - 7467

Published: Jan. 1, 2019

A transition-metal-free approach was developed to synthesize chromones from o-bromoaryl ynones and benzaldehyde oxime by sequential C–O bond formation.

Language: Английский

Citations

21
Catalyst- and Additive-Free Annulation of Ynediones and (Iso)Quinoline N-Oxides: An Approach to Synthesis of Pyrrolo[2,1-a]Isoquinolines and Pyrrolo[1,2-a]Quinolines DOI

Wan-Wan Yang,

Ya-Fang Ye,

Lulu Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 86(1), P. 169 - 177

Published: Nov. 30, 2020

A simple and effective annulation of ynediones (iso)quinoline N-oxides was developed to afford various functionalized pyrrolo[2,1-a]isoquinolines pyrrolo[1,2-a]quinolines in moderate excellent yields. This protocol underwent a tandem [3 + 2] cycloaddition/ring-opening/N-nucleophilic addition, which exhibited high regioselectivity, broad substrate tolerance, atom economy under catalyst-, additive-free, air conditions. Moreover, indolizine also successfully prepared using pyridine N-oxide.

Language: Английский

Citations

18
Base-mediated benzannulation of α-cyanocrotonates with ynones: facile synthesis of benzonitriles and fluorenes DOI
Maneesh Kumar Reddy Singam, Attunuri Nagireddy, Maddi Sridhar Reddy

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(8), P. 2370 - 2374

Published: Jan. 1, 2020

Benzonitriles and cyanofluorenes have been rapidly obtained via the [3 + 3] benzannulation of readily available alkynones α-cyanocrotonates using KOtBu as only reagent EtOH (and CO2) is by-product.

Language: Английский

Citations

16
Regioselective benzannulation of allylic sulfur ylides with ynones: a rapid access to substituted thioanisoles DOI

Matam Parameshwar,

Maneesh Kumar Reddy Singam, Attunuri Nagireddy

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(87), P. 13457 - 13460

Published: Jan. 1, 2020

The efficiency and selectivity of annulation reactions are often difficult to control in the presence multiple potential reactive centers, like case allylic sulfur ylides (ASY). Here, we describe a novel base mediated [3+3] benzannulation ASY readily available alkynones, which accomplishes regioselective formation multisubstituted thioanisoles, highly sought after chemical scaffolds. A new reactivity pattern has been unearthed, where it acted as both 3C component source benzannulation. Use widely base, operational simplicity broad substrate scope additional salient features conversion.

Language: Английский

Citations

15