Synthesis of N-functionalized 2,3-disubstituted benzofurans/naphthofurans from para-quinone methides and isocyanides via the [4 + 1] annulation pathway DOI
Someshwar B. Kale, Manish Kumar, Dinesh R. Shinde

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3746 - 3751

Опубликована: Янв. 1, 2023

Synthesis of 2-amino substituted benzo- and naphtho-furans via [4 + 1] cycloaddition 2-hydroxy-substituted p -QMs various alkyl/aryl isocyanides has been achieved by using Sc(OTf) 3 as the catalyst.

Язык: Английский

An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds DOI
Daqian Wang,

Jing Sun,

Ying Han

и другие.

Organic Letters, Год журнала: 2022, Номер 24(42), С. 7790 - 7795

Опубликована: Окт. 14, 2022

We have developed an efficient protocol for the construction of polycyclic dihydrobenzofuran spirooxindole scaffolds via base promoted cascade annulation Morita-Baylis-Hillman (MBH) carbonates isatins with ortho-hydroxychalcones or ortho-hydroxy-β-nitrostyrenes. The complex compounds were conveniently synthesized in satisfactory yields and high diastereoselectivity. This provides a swift convenient approach assembly diverse highly functionalized spirooxindoles also features broad substrate scope, molecular convergence, excellent atomic economy.

Язык: Английский

Процитировано

26

Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones with iodonium ylides to give substituted isocoumarins DOI

Mingshuai Zhang,

Longkun Chen,

Donghan Liu

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(26), С. 12274 - 12278

Опубликована: Янв. 1, 2023

A wide variety of isocoumarin derivatives are easily constructed via a Rh( iii )-catalyzed C–H bond activation/annulation cascade reaction.

Язык: Английский

Процитировано

15

Recent advances in the cyclization of para-quinone methides DOI
Xianping Liu,

Yining Ren,

Longzhi Zhu

и другие.

Tetrahedron, Год журнала: 2023, Номер 148, С. 133655 - 133655

Опубликована: Окт. 9, 2023

Язык: Английский

Процитировано

15

Asymmetric synthesis of spiro-structural 2,3-dihydrobenzofuransviathe bifunctional phosphonium salt-promoted [4 + 1] cyclization ofortho-quinone methides with α-bromoketones DOI
Song Zhang, Xiaojun Yu,

Jianke Pan

и другие.

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(22), С. 3799 - 3803

Опубликована: Янв. 1, 2019

A practical and scalable method for highly stereoselective construction of spiro-2,3-dihydrobenzofuransviacyclization ofortho-quinone methides α-bromoketones by bifunctional phosphonium salt catalysis was developed.

Язык: Английский

Процитировано

37

Synthesis of 1,4-Dihydroquinolines and 4H-Chromenes via Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of para-Quinone Methides and Ynals DOI
Junwei Wang,

Quanjin Rong,

Lei Zhao

и другие.

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(17), С. 11240 - 11249

Опубликована: Авг. 11, 2020

An organocatalytic domino aza/oxa-Michael/1,6-addition reaction of ortho-tosylaminophenyl or ortho-hydroxyphenyl-substituted para-quinone methides and ynals has been developed. In the presence 20 mol % morpholine, this unprecedented cascade occurs readily in good yield (up to 99%), providing a highly efficient synthetic approach synthetically valuable 1,4-dihydroquinolines 4H-chromenes.

Язык: Английский

Процитировано

34

Metal-free synthesis of triarylated (Z)-nitrones via H2O-mediated 1,3-dipolar transfer under aerobic conditions DOI
Ke Chen, Wen‐Juan Hao, Shu‐Jiang Tu

и другие.

Green Chemistry, Год журнала: 2019, Номер 21(3), С. 675 - 683

Опубликована: Янв. 1, 2019

A new and environmentally benign protocol aimed at the generation of triarylated (Z)-nitrones in generally good yield has been developed via metal- catalyst-free H2O-mediated 1,3-dipolar transfer reaction para-quinone methides (p-QMs) with diarylated nitrones under aerobic conditions.

Язык: Английский

Процитировано

31

Synthesis of Functionalized Benzofurans from para-Quinone Methides via Phospha-1,6-Addition/O-Acylation/Wittig Pathway DOI
Yan-Cheng Liou, Praneeth Karanam, Yeong‐Jiunn Jang

и другие.

Organic Letters, Год журнала: 2019, Номер 21(19), С. 8008 - 8012

Опубликована: Сен. 19, 2019

An efficient synthesis of functionalized benzofurans is achieved under mild and metal-free conditions from stable para-quinone methides by treatment with phosphine, acyl chloride, a base. This one-pot phospha-1,6-addition/O-acylation/Wittig reaction also demonstrated catalytic similar efficacy.

Язык: Английский

Процитировано

31

Base-Mediated Annulation of ortho-Iminophenols and ortho-Vinylphenols with MBH Carbonates of Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran Derivatives DOI
Daqian Wang, Xing Liu,

Jing Sun

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15472 - 15489

Опубликована: Окт. 15, 2024

We have developed a convenient synthetic protocol for efficient construction of significant dihydrobenzofuran and benzofuran scaffolds by Lewis base-mediated annulation reaction ortho-iminophenols ortho-vinylphenols with MBH carbonates isatins under mild metal-free conditions. The selective generation different kinds derivatives was successfully achieved employing substituted isatin-derived ortho-N-tosyliminophenols ortho-vinylphenols. features included broad substrate scopes, excellent functional group compatibility, high molecular diversity, atomic economy.

Язык: Английский

Процитировано

4

Time‐Economical Synthesis of Bis‐Spiro Cyclopropanes via Cascade 1,6‐Conjugate Addition/Dearomatization Reaction of para‐Quinone Methides with 3‐Chlorooxindoles DOI

Jing‐Ru Zhang,

Hai‐Shan Jin, Jin Sun

и другие.

European Journal of Organic Chemistry, Год журнала: 2020, Номер 2020(31), С. 4988 - 4994

Опубликована: Июнь 24, 2020

A spirocyclopropanation of para ‐quinone methides with 3‐chlorooxindoles that proceeds via cascade 1,6‐conjugate addition/dearomatization reaction has been established, leading to a novel class bis‐spiro compounds in concise, rapid, and practical manner. This transformation could be completed high yields at room temperature within 5 min. The resulting cyclopropane derivatives are great interest because their potential biological activity further potential.

Язык: Английский

Процитировано

26

Base‐Mediated [4+1] Annulation Strategy for Modular Assembly of Alkynyl/Carboxylated Dihydrobenzofurans DOI Open Access

Yangzilin Kong,

Yinsong Wu,

Yanan Liu

и другие.

European Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 17, 2025

Abstract An efficient and operational [4+1] annulation strategy toward functional dihydrobenzofurans from 2‐bromomalonates in situ generated alkynyl o ‐quinone methides (from ‐hydroxyphenyl propargylamines) has been developed. Without the need for pre‐dried solvent inert atmosphere protection, a broad range of substituted propargylamines are well‐tolerated, producing expected alkynyl/carboxylated with good to high yields. Furthermore, gram‐scale synthesis valuable alkenyl/carboxylated construction were conducted provide great potential value medicinal chemistry other related disciplines.

Язык: Английский

Процитировано

0