Diastereoselective construction of pyrrolo[2,1-a]isoquinoline-based bispirooxindoles through a three-component [3 + 2] cycloaddition DOI

Jiaomei Guo,

Yang Zhao, Dongmei Fang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2018, Номер 16(33), С. 6025 - 6034

Опубликована: Янв. 1, 2018

An efficient three-component one-pot [3 + 2] cycloaddition of isatins, 1,2,3,4-tetrahydroisoquinolines and methyleneindolinones has been developed. This reaction proceeded in a highly diastereoselective manner to afford wide range pyrrolo[1,2-a]isoquinoline-based bispirooxindoles up 91% yields. Additionally, gram-scale experiment some chemical transformations were conducted.

Язык: Английский

Transition metal-catalyzed synthesis of spirooxindoles DOI Creative Commons

Padinjare Veetil Saranya,

Mohan Neetha,

Thaipparambil Aneeja

и другие.

RSC Advances, Год журнала: 2021, Номер 11(13), С. 7146 - 7179

Опубликована: Янв. 1, 2021

Spirooxindoles are used as anticancer-, antiviral-, antimicrobial agents etc. The use of transition metals catalysts for the synthesis spirooxindoles is advancing rapidly. Here, we focus on recent advances in metal-catalyzed spirooxindoles.

Язык: Английский

Процитировано

59

Recent advances in aza Friedel–Crafts reaction: strategies for achiral and stereoselective synthesis DOI Creative Commons
Ameni Hadj Mohamed, Nicolas Masurier

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1847 - 1866

Опубликована: Янв. 1, 2023

The aza-Friedel–Crafts (aza-FC) reaction is a very powerful tool for forming C–C and C–N bonds, based on an acid-catalyzed addition of electron-rich aromatic compounds to imines.

Язык: Английский

Процитировано

23

Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis DOI
Yuheng Wang, Pan Hu, Xirui Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1314 - 1321

Опубликована: Янв. 1, 2024

A new class of chiral bipyridine-2NO ligands, which incorporate the advantages both bipyridine skeleton and pyrroloimidazolone-based N -oxide moiety, was developed.

Язык: Английский

Процитировано

9

Electrocatalytic Annulation–Iodosulfonylation of Indole‐Tethered 1,6‐Enynes to Access Pyrrolo[1,2‐a]indoles DOI

Ya‐Yu Yuan,

Xi Chen,

J. Wang

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(10)

Опубликована: Янв. 9, 2024

Abstract We present the first example of electrocatalytic three‐component annulation–iodosulfonylation indole‐tethered 1,6‐enynes with arylsulfonyl hydrazides and KI for accessing various iodosulfonated pyrrolo[1,2‐ a ]indoles in moderate to excellent yields high stereospecificity. This electrosynthesis opens new avenues construction skeleton good functional group compatibility under environmentally benign condition. Based on control experiments cyclic voltammetry data, we suggested plausible reaction mechanism which included anodic oxidation, homolysis iodide, radical addition, 5 ‐ exo dig cyclization, coupling or nucleophilic attack iodide ions cascade.

Язык: Английский

Процитировано

8

Metal-free diastereoselective construction of bridged ketal spirooxindoles via a Michael addition-inspired sequence DOI

Yan‐Shuo Zhu,

Jing Zhou,

Shaojing Jin

и другие.

Chemical Communications, Год журнала: 2017, Номер 53(81), С. 11201 - 11204

Опубликована: Янв. 1, 2017

A TfOH-catalyzed highly diastereoselective Michael addition/ketalization sequence of 3-hydroxyoxindoles and ortho-hydroxychalcones was developed, leading to biologically important bridged ketal spirooxindoles in moderate excellent yields. Moreover, some chemical transformations were carried out further extend the structural complexity diversity.

Язык: Английский

Процитировано

71

Visible‐Light‐Promoted Difluoromethylation/Cyclization of 1‐Acryloyl‐2‐cyanoindole for Construction of Difluoromethylated Pyrrolo[1,2‐a]indolediones DOI

Hongzhao Qu,

Jinwei Yuan, Zhendong Feng

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(5), С. 1158 - 1164

Опубликована: Янв. 10, 2024

Abstract A visible‐light‐promoted cascade difluoromethylation/cyclization reaction to access various difluoromethylated pyrrolo[1,2‐ a ]indolediones was developed using difluoromethyltriphenylphosphonium bromide salt as the difluoromethylating reagent. possible radical mechanism has been investigated and proven single electron transfer (SET) procedure.

Язык: Английский

Процитировано

7

Py-2NO ligand enabled Ni(ii)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters DOI

Zi‐Yue Chen,

Xirui Wang,

Ke‐Lan Xu

и другие.

New Journal of Chemistry, Год журнала: 2024, Номер 48(4), С. 1688 - 1695

Опубликована: Янв. 1, 2024

This work diversified the Py-2NO ligand library recently developed by our group and further expanded application of chiral ligands in asymmetric catalysis.

Язык: Английский

Процитировано

6

Synthesis of CF3-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site DOI

Manqing Wang,

Shengnan Yan,

Bin Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7828 - 7842

Опубликована: Май 22, 2024

Presented herein is a novel synthesis of CF

Язык: Английский

Процитировано

6

Diastereoselective Construction of Indole-Bridged Chroman Spirooxindoles through a TfOH-Catalyzed Michael Addition-Inspired Cascade Reaction DOI

Jiaomei Guo,

Xuguan Bai,

Qilin Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2018, Номер 83(7), С. 3679 - 3687

Опубликована: Март 13, 2018

The first highly diastereoselective Michael addition/condensation/Friedel–Crafts alkylation cascade reaction of 3-indolyl-substituted oxindoles with ortho-hydroxychalcones was established, which afforded a wide range polycyclic indole-bridged chroman spirooxindoles novel and complex scaffolds in moderate to excellent yields.

Язык: Английский

Процитировано

58

Bifunctional Squaramide-Catalyzed Asymmetric [3 + 2] Cyclization of 2-(1-Methyl-2-oxoindolin-3-yl)malononitriles with Unsaturated Pyrazolones To Construct Spirooxindole-Fused Spiropyrazolones DOI
Ye Lin, Bo‐Liang Zhao, Da‐Ming Du

и другие.

The Journal of Organic Chemistry, Год журнала: 2019, Номер 84(16), С. 10209 - 10220

Опубликована: Июль 18, 2019

The present paper reports a highly stereoselective synthesis of spirooxindole-fused spiropyrazolones through the asymmetric [3 + 2] cyclization reaction 2-(1-methyl-2-oxoindolin-3-yl)malononitriles with unsaturated pyrazolones under mild conditions. With only 1 mol % bifunctional squaramide catalyst, series chiral dispirocyclic pyrazolone derivatives were attained in high yields (85–97%) excellent stereoselectivities (up to >99% ee and all cases >20:1 dr). Moreover, gram-scale further transformation products also demonstrated.

Язык: Английский

Процитировано

48