An Approach to Functionally Embellished o-Alkynylbenzoates or Furan-3(2H)-ones from Diynones and DMAD: Controlled Divergence and Product Selectivity

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3945 - 3953

Опубликована: Март 2, 2023

The discovery of reaction regime controlled product diversification in a one-pot between diynones and dimethyl-1,3-acetonedicarboxylate (DMAD) to selectively furnish either functionally unique pentasubstituted o-alkynylbenzoates or fully substituted furan-3(2H)-ones is delineated. potential these two versatile platforms enter new utilitarian chemical space has also been explored.

Язык: Английский

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Synthesis of γ-Pyrones and N-Methyl-4-pyridones via the Au Nanoparticle-Catalyzed Cyclization of Skipped Diynones in the Presence of Water or Aqueous Methylamine

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(13), С. 8525 - 8533

Опубликована: Июнь 9, 2022

Supported Au nanoparticles on TiO2 catalyze the hydration/6-endo cyclization of skipped diynones to γ-pyrones in aqueous dioxane, via triple bond activation. The isomeric 3(2H)-furanones which could be formed through a competing and often prevailing 5-exo pathway using homogeneous ionic Au(I) catalysts were not seen. reaction does proceed initial 1,3-transposition their corresponding conjugated 1,3-diynone isomers. If methylamine is added, N-methyl-4-pyridones are exclusively 69-79% yields an analogous hydroamination/Au-catalyzed 6-endo pathway.

Язык: Английский

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Advances in organocatalysis of the Michael reaction by tertiary Phosphines

Catalysis Reviews, Год журнала: 2023, Номер 66(4), С. 1518 - 1607

Опубликована: Фев. 26, 2023

Tertiary phosphines have been recognized as powerful organocatalysts for the Michael reaction, which is one of most important atom-economical methods carbon-carbon and carbon-heteroatom bond construction. In presence tertiary phosphines, a vast array acceptors donors can be coupled with each other under neutral metal-free conditions to produce useful densely functionalized molecules. This review highlights role phosphine-catalyzed reaction in cutting-edge areas, such asymmetric synthesis, natural products drug design, polymer material science. As central part catalysis science, kinetic mechanistic issues are also discussed when possible. The organized by type acceptor donor used reaction.

Язык: Английский

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Base-Promoted Decarboxylative Annulation of Methyl 2-(2-Bromophenyl)acetates and Ynones to Access Benzoxepines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(5), С. 3079 - 3088

Опубликована: Фев. 17, 2023

A simple and efficient base-mediated decarboxylative annulation of ynones with methyl 2-(2-bromophenyl)acetates has been developed. broad range benzoxepines were prepared a substrate scope high regioselectivity in moderate to excellent yields under transition-metal-free conditions. This method proceeds through tandem [2 + 4] annulation, ring-opening reaction, the intramolecular nucleophilic aromatic substitution reaction. Additionally, key intermediates successfully obtained characterized unambiguously by single-crystal X-ray crystallography, which could favorably support mechanism. Furthermore, gram-scale reaction synthetic applications for further functionalization are also studied.

Язык: Английский

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Ag(I)-Mediated Annulation of 2-(2-Enynyl)pyridines and Propargyl Amines to Access 1-(2H-Pyrrol-3-yl)indolizines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 304 - 312

Опубликована: Дек. 21, 2023

An effective Ag(I)-mediated annulation of 2-(2-enynyl)pyridines and propargyl amines was developed, unexpectedly affording a broad range functionalized 1-(2H-pyrrol-3-yl)indolizines in moderate to excellent yields. The developed method is characterized by operational simplicity, ready availability starting materials, high regioselectivity, substrate scope under mild reaction conditions. Ag(I)-promoted cyclization possibly results the formation spiroindolizine, ring-opening rearrangement which may give 1-(2H-pyrrol-3-yl)indolizine. Furthermore, gram-scale synthetic transformations are also studied.

Язык: Английский

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Base-Promoted Divergent Annulation of Conjugated Ynones and Methyl 2-(Cyanomethyl)benzoates to Access 1-Naphthols and Xanthones

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(18), С. 12132 - 12147

Опубликована: Сен. 5, 2022

A facile and efficient base-mediated divergent annulation of methyl 2-(cyanomethyl)benzoates conjugated ynones has been described. broad range 1-naphthols xanthones were formed in moderate to excellent yields. The notable features this protocol include readily available precursors, substrate scope, complete regioselectivity, substrate-controlled synthesis. gram-scale preparation synthetic transformations the resulting demonstrate their utility.

Язык: Английский

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Lewis acid-catalyzed chemo- and stereoselective addition of pyrroles to skipped diynones: en route to novel pyrrole-based ketocyanine dyes and alkyne-tethered enones

Dyes and Pigments, Год журнала: 2024, Номер 229, С. 112293 - 112293

Опубликована: Июнь 18, 2024

Язык: Английский

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

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14005 - 14015

Опубликована: Окт. 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.

Язык: Английский

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Six-membered ring systems: with O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 487 - 557

Опубликована: Янв. 1, 2023

Язык: Английский

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Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11567 - 11575

Опубликована: Авг. 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.

Язык: Английский

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