Bifunctional Squaramide‐Catalyzed Asymmetric Michael/Cyclization Reactions of 3‐Hydroxychromenones with Isatylidenemalononitriles DOI

Xue‐Yang Geng,

Da‐Ming Du

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(20)

Published: May 24, 2024

Abstract A squaramide‐catalyzed asymmetric Michael/cyclization tandem reaction between 3‐hydroxychromenones and isatylidenemalononitriles was developed. Using this strategy, a wide scope of spiro[indoline‐3,4′‐pyrano[3,2‐b]chromene] derivatives, which combined chromone, pyran, indolone in one molecule, could be obtained moderate to excellent yields (up 94 %) with enantioselectivities 95 % ee). In addition, the scaled‐up experiment also confirmed synthetic practicality strategy.

Language: Английский

Coumarin-3-formylpyrazoles as 3-carbon synthons in cyclocondensation for the synthesis of spiro-fused pentacyclic spirooxindoles DOI
Chuan-Wen Lei, Chuanbao Zhang, Zhen‐Hua Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 18(5), P. 845 - 850

Published: Dec. 30, 2019

Coumarin-3-formylpyrazoles have been synthesized and applied as 3-carbon synthons in reaction with 3-hydroxyoxindoles by using DABCO the catalyst. A range of structurally diverse spiro-fused pentacyclic spirooxindoles, bearing a spirooxindole-γ-lactone 3,4-dihydrocoumarin substructure, could be smoothly obtained good to excellent yields (up 99%) diastereoselectivities (all cases >20 : 1 dr). The asymmetric version this tandem was preliminarily investigated chiral organocatalysts.

Language: Английский

Citations

15
Organocatalyzed asymmetric cascade Mannich/cyclization of 3-isothiocyanato oxindoles with cyclic ketimines for the synthesis of polycyclic spiro-thioimidazolidine-oxindoles DOI
Chuanbao Zhang,

Pei‐Hao Dou,

Jian‐Qiang Zhao

et al.

Tetrahedron, Journal Year: 2020, Volume and Issue: 76(16), P. 131116 - 131116

Published: March 10, 2020

Language: Английский

Citations

13
Evaluation of the cellular protection by novel spiropyrazole compounds in dopaminergic cell death DOI

Jamila Zaiter,

Achraf Hibot,

Abderrafia Hafid

et al.

European Journal of Medicinal Chemistry, Journal Year: 2021, Volume and Issue: 213, P. 113140 - 113140

Published: Jan. 8, 2021

Language: Английский

Citations

12
Asymmetric Construction of Bis‐Spirocyclic Pyrazolones Bearing Vicinal Quaternary Carbon Centers DOI
Mengjie Yang,

Aiqi Xue,

Xingfu Wei

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: April 8, 2024

Abstract A catalytic asymmetric (3+2) cyclization of pyrazolone‐based MBH adducts with alkylidenyl isoxazolones was presented by using DMAP‐derived chiral catalyst, affording bis‐spirocyclic pyrazolones bearing vicinal all‐carbon quaternary stereocenters within an imbedded cyclopentene ring scaffold in good yields excellent stereoselectivities under mild conditions.

Language: Английский

Citations

1
Bifunctional Squaramide‐Catalyzed Asymmetric Michael/Cyclization Reactions of 3‐Hydroxychromenones with Isatylidenemalononitriles DOI

Xue‐Yang Geng,

Da‐Ming Du

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(20)

Published: May 24, 2024

Abstract A squaramide‐catalyzed asymmetric Michael/cyclization tandem reaction between 3‐hydroxychromenones and isatylidenemalononitriles was developed. Using this strategy, a wide scope of spiro[indoline‐3,4′‐pyrano[3,2‐b]chromene] derivatives, which combined chromone, pyran, indolone in one molecule, could be obtained moderate to excellent yields (up 94 %) with enantioselectivities 95 % ee). In addition, the scaled‐up experiment also confirmed synthetic practicality strategy.

Language: Английский

Citations

1