Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones DOI
Ting Chen,

Mao-Chun Ye,

Ting Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract An efficient, practical, and scalable Cs 2 CO 3 ‐catalyzed [4+2] annulation reaction between ynones acetates is presented, wherein serve as the four‐atom partners. This methodology facilitates synthesis of substituted 2‐pyrones with yields ranging from good to excellent. The ready availability starting materials, coupled simplicity protocol, renders this approach highly amenable preparation a diverse range 2‐pyrones. Furthermore, feasibility on gram scale its application in potent selective cyclooxygenase‐2 inhibitor underscore practical significance utility method.

Language: Английский

Transition-Metal-Free Synthesis of 3-Acyl Chromones by the Tandem Reaction of Ynones and Methyl Salicylates DOI

Ya-Fang Ye,

Feng Li, Jiale Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14005 - 14015

Published: Oct. 10, 2022

A facile and effective tandem reaction of ynones methyl salicylates was developed to obtain a broad range 3-acyl chromones in moderate-to-excellent yields. This protocol underwent Michael addition cyclization process, which exhibited easily accessible substrates, substrate scope, high regioselectivity under mild transition-metal-free conditions. Moreover, gram-scale further chemical transformation the products were also studied.

Language: Английский

Citations

6

Molecular Rearrangements DOI

J. M. Coxon

Organic Reaction Mechanisms/Organic reaction mechanisms, Journal Year: 2023, Volume and Issue: unknown, P. 519 - 554

Published: Jan. 20, 2023

A review of pericyclic biosynthetic reactions reports that there are many 'pericyclase' enzymes in nature catalyse such transformations. Using the Cope rearrangement as a model process, report shows synergy between acceptor and donor groups can allow rational design interrupted aborted reactions. The Brandi–Guarna 5-spirocyclopropane isoxazolidines has been investigated by computational methods to rationalize competing formation tetrahydropyridones enaminones. Nazarov cyclization reported give substituted cyclopentenones with iodine catalyst. thermal Overman enantioenriched cyclic allylic alcohols tertiary amines. Ring expansion situ generated cyclopropylmethyl cations via Wagner–Meerwein cyclobutanes involve planar cation loss chiral information case precursors.

Language: Английский

Citations

3

Base-promoted cyclization ofortho-hydroxyacetophenones within situgenerated cyclopropenes: diastereoselective access to spirobenzo[b]oxepines and related precursors DOI

Meher Prakash,

Sampak Samanta

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(9), P. 2001 - 2014

Published: Jan. 1, 2023

Excellent diastereoselective access to spirobenzo[ b ]oxepines via a [5 + 2] spirocyclization reaction of ortho -hydroxyacetophenones and 2-aroyl-1-chlorocyclopropanecarboxylates triggered by Cs 2 CO 3 was developed.

Language: Английский

Citations

3

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

Citations

0

Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones DOI
Ting Chen,

Mao-Chun Ye,

Ting Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract An efficient, practical, and scalable Cs 2 CO 3 ‐catalyzed [4+2] annulation reaction between ynones acetates is presented, wherein serve as the four‐atom partners. This methodology facilitates synthesis of substituted 2‐pyrones with yields ranging from good to excellent. The ready availability starting materials, coupled simplicity protocol, renders this approach highly amenable preparation a diverse range 2‐pyrones. Furthermore, feasibility on gram scale its application in potent selective cyclooxygenase‐2 inhibitor underscore practical significance utility method.

Language: Английский

Citations

0