Metal-free synthesis of quinoline-2,4-dicarboxylate derivatives using aryl amines and acetylenedicarboxylates through a pseudo three-component reaction DOI
Saghir Ali,

Abu T. Khan

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(32), P. 7041 - 7050

Published: Jan. 1, 2021

An efficient, useful and one-pot protocol for the synthesis of quinoline-2,4-dicarboxylate scaffolds is accomplished from aryl amines dimethyl/diethyl acetylenedicarboxylates using 20 mol% molecular iodine as a catalyst in acetonitrile at 80 °C.

Language: Английский

Metal-free three-component reactions of alkynes for the construction of 3,4-difunctionalized benzo[h]coumarins DOI

Shendan Xia,

Chaojie Wang,

Yuyan Xu

et al.

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel approach for constructing 3,4-difunctionalized benzo[ h ]coumarins through a metal-free multicomponent reactions with mild reaction conditions.

Language: Английский

Citations

0
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

26
Substituent-controlled chemoselective synthesis of multi-substituted pyridones via a one-pot three-component cascade reaction DOI
Shitao Liu, Jisen Li, Jun-Jie Lin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(6), P. 1130 - 1134

Published: Jan. 1, 2020

A substituent-controlled chemoselective cycloaddition reaction which afforded a variety of 2-pyridones and 4-pyridones in good to excellent yields, respectively, has been developed.

Language: Английский

Citations

25
Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System DOI

Qi-Qi Hu,

Yanting Gao, Jiachen Sun

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(22), P. 9000 - 9005

Published: Nov. 8, 2021

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where methyl group azaarenes represents uniquely reactive input in reaction. This method broad substrate scope mild conditions. Furthermore, these derivatives had been directly used as bidentate ligands metal-catalyzed reactions.

Language: Английский

Citations

21
Regioselective Synthesis of 2,4-Diaryl-6-trifluoromethylated Pyridines through Copper-Catalyzed Cyclization of CF3-Ynones and Vinyl Azides DOI
Jixin Wang,

Dang Xuan Ba,

Mengqi Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(9), P. 6423 - 6432

Published: April 27, 2021

A novel copper-catalyzed cyclization of readily available vinyl azides with CF3-ynones is steadily achieved under mild conditions to furnish the versatile 2,4-diaryl-6-trifluoromethylated pyridine products, which are great interest in medicinal chemistry. The generation iminophosphorane intermediates from through Staudinger-Meyer reaction ensures subsequent 1,4-addition process this transformation.

Language: Английский

Citations

18
Photoinduced Regioselective Perfluoroalkylation/Cyclization Cascade of 3‐Aza‐1,5‐Dienes: Access to Pentasubstituted 3‐Perfluoroalkyl‐1,3‐Dihydropyrrol‐2‐Ones DOI
Ruihan Yang,

Danna Chen,

Shi‐Yi Lin

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(31)

Published: July 12, 2023

Abstract A visible light‐induced perfluoroalkylative cyclization of 3‐aza‐1,5‐dienes leading to pentasubstituted 1,3‐dihydropyrrole‐2‐ones is presented. The reaction regiospecific, for the radical adds across acrylamido moiety, whereas enaminic double bond functions as a built‐in trap. It could be carried out on 2‐gram scale, and sunlight usable light source. Other virtues protocol include short time, low catalyst loading, mild conditions broad substrate scope.

Language: Английский

Citations

6
Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges DOI
Imtiaz Khan, Aliya Ibrar, Sumera Zaib

et al.

Topics in Current Chemistry, Journal Year: 2021, Volume and Issue: 379(1)

Published: Jan. 5, 2021

Language: Английский

Citations

13
Iron‐Mediated C−H Functionalization of Unactivated Alkynes for the Synthesis of Derivatized Dihydropyrrolones: Regioselectivity Under Thermodynamic Control DOI

Austin C. Durham,

Cindy R. Liu,

Yiming Wang

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(45)

Published: May 19, 2023

Cyclopentadienyliron dicarbonyl-based complexes present opportunities for underexplored disconnections in synthesis. Access to challenging dihydropyrrolone products is achieved by propargylic C-H functionalization of alkynes the formation cyclic organoiron species. Excellent regioselectivity unsymmetrical observed many cases. Notably, under these stoichiometric conditions diverges from those previously catalysis, occurring at more-substituted terminus alkyne, allowing methine and quaternary centers. Divergent demetallation intermediate gives access chemically diverse which are amenable further functionalization.

Language: Английский

Citations

5
Construction of Polyfunctionalized 2,4-Dioxa-8-azaspiro[5.5]undec-9-enes and 2,4,8-Triazaspiro[5.5]undec-9-enes via a Domino [2+2+2] Cycloaddition Reaction DOI
Dan Liu,

Jing Sun,

Ju Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(2), P. 1827 - 1842

Published: Jan. 2, 2021

The three-component reaction of α,β-unsaturated N-arylaldimines, dialkyl but-2-ynedioates, and 2-arylidene Meldrum acids in DCM at room temperature gave mixtures cis/trans-11-aryl-7-styryl-2,4-dioxa-8-azaspiro[5.5]undec-9-enes satisfactory yields. similar with 2-arylidene-N,N′-dimethylbarbituric afforded cis-11-phenyl-7-styryl-2,4,8-triazaspiro[5.5]undec-9-enes as major products. On the other hand, or cis/trans-isomeric spirocompounds yields high diastereoselectivity. This domino [2+2+2] cycloaddition proceeded sequential nucleophilic addition N-arylaldimine to an electron-deficient alkyne, Michael addition, annulation process. stereochemistry all cis/trans isomeric was clearly elucidated by determination 33 single-crystal structures. diastereoselectivity correlated DFT calculations.

Language: Английский

Citations

12
Progress in Construction of 2H-Pyrrol-2-ones Skeleton DOI
Donghan Liu,

Xihang Lu,

Zhangmengjie Chai

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(1), P. 57 - 57

Published: Jan. 1, 2023

Language: Английский

Citations

4