Isoxazoles as efficient alkyne amination reagents in divergent heterocycle synthesis

Chemical Society Reviews, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This review summarizes the latest trends and developments of isoxazole-enabled alkyne amination reactions their applications in divergent heterocycle synthesis.

Язык: Английский

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Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(12), С. 3127 - 3165

Опубликована: Окт. 11, 2021

Abstract Isoxazoles are an important class of heterocycles with nitrogen and oxygen in a 1,2‐relationship. They find wide applications synthetic organic chemistry part several drug molecules. Since the last two decades, great progress has been achieved synthesis functionalization isoxazoles, which transition metal catalysis played pivotal role towards achieving this goal. In particular, (TM)‐mediated site‐selective functionalizations isoxazoles retain pharmacologically synthetically valuable isoxazole skeleton, highly appealing. This comprehensive review is solely dedicated to TM‐mediated wherein we have included as directing groups (DG) for TM‐catalyzed C−H reactions, direct functionalization, along cross‐coupling reactions annulation finally ring‐opening under TM‐catalysis also discussed. Also, incorporated discussions on reaction designs, their advantages limitations, mechanistic details challenges that need be addressed inspire medicinal chemists explore new arenas make use key scaffold.

Язык: Английский

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Gold‐Catalyzed Reaction of Anthranils with Alkynyl Sulfones for the Regioselective Formation of 3‐Hydroxyquinolines

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(7), С. 1233 - 1238

Опубликована: Март 2, 2022

Abstract The gold‐catalyzed regioselective formation of 3‐hydroxyquinoline is accessed by combining anthranils and alkynyl sulfones. selective scission the epoxide intermediate stems from thermodynamic stability difference resultant cation according to quantum chemical calculations. subsequent semi‐pinacol rearrangement leads 1,2‐shift an aryl or alkyl group originating sulfone. A gram‐scale synthesis further manifests viability protocol for preparation this important scaffold. magnified image

Язык: Английский

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Copper-Catalyzed Formal [4 + 1] Annulation of Diynes with Isoxazoles: Synthesis of Pyrrolo[3,4-b]indoles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 14, 2025

Catalytic annulation of isoxazoles with alkynes is an efficient methodology for the assembly N-heterocyclic architectures, and most reactions require noble-metal catalysts. Herein, we disclose a copper-catalyzed formal [4 + 1] 1,6-diynes atom-economical construction biologically important pyrrolo[3,4-b]indoles in high yields via vinyl cation intermediates, which significantly different from previous annulations involving α-imino metal carbene intermediates. Interestingly, preliminary results have been obtained related catalytic atroposelective transformation. Computational mechanistic studies are employed to elucidate reaction mechanism.

Язык: Английский

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Divergent Access to Polycyclic N-Heterocyclic Compounds through Büchner-Type Dearomatization Enabled Cycloisomerization of Diynamides under Gold Catalysis

Organic Letters, Год журнала: 2022, Номер 24(23), С. 4298 - 4303

Опубликована: Июнь 6, 2022

Catalytic dearomatization has been considered as a valuable approach to convert readily accessible flat molecules products with three-dimensional frameworks. Herein, an unprecedented gold-catalyzed oxidative Büchner-type cyclopropanation is described that enables the cycloisomerization of diynamides. By variation position substituents on phenyl ring, variety fused N-heterocyclic challenging structural skeletons were obtained divergently.

Язык: Английский

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Gold‐Catalyzed Cascade Reaction of Diynamides with Allylic Alcohols: A Versatile Platform to Allenamide, 2‐Aminofuran and Bridged [2.2.2]Octadiene Derivatives

Chemistry - A European Journal, Год журнала: 2023, Номер 29(33)

Опубликована: Март 28, 2023

Transition metal-catalyzed divergent synthesis through alternation of the catalyst is appealing, as it provides an operationally simple way to access different valuable products, while using same reactants starting materials. Herein, a gold-catalyzed cascade reaction conjugated diynamides with allylic alcohols described. By variation catalysts, substituted allenes and furans could be obtained selectively. Mechanistic studies indicate that, after addition alcohol gold-activated diynamide, [3,3]-sigmatropic rearrangement would take place lead formation common reactive intermediate, which further convert final products Further structure has unveiled additional sequence involving intramolecular Himbert arene/allene Diels-Alder cycloaddition afford series dearomatized bearing bicyclo[2,2,2]octadiene core.

Язык: Английский

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1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry

Molecules, Год журнала: 2023, Номер 28(11), С. 4564 - 4564

Опубликована: Июнь 5, 2023

1,3-butadiynamides—the ethynylogous variants of ynamides—receive considerable attention as precursors complex molecular scaffolds for organic and heterocyclic chemistry. The synthetic potential these C4-building blocks reveals itself in sophisticated transition-metal catalyzed annulation reactions metal-free or silver-mediated HDDA (Hexa-dehydro-Diels–Alder) cycloadditions. 1,3-Butadiynamides also gain significance optoelectronic materials less explored views on their unique helical twisted frontier orbitals (Hel-FMOs). present account summarizes different methodologies the synthesis 1,3-butadiynamides followed by description structure electronic properties. Finally, surprisingly rich chemistry versatile is reviewed compiling exciting reactivity, specificity opportunities synthesis. Besides chemical transformations use synthesis, a focus set mechanistic understanding 1,3-butadiynamides—suggesting that are not just simple alkynes. These ynamides have own character reactivity reflect new class remarkably useful compounds.

Язык: Английский

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Synthesis of 2‐Aminopyrrolo[1,2‐b]pyridazines via Gold(I)‐Catalyzed Chemoselective Hydroamination/Hydroarylation Cascade of 1,3‐Diynamides with 1‐Aminopyrroles

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 1088 - 1092

Опубликована: Март 16, 2023

Abstract The synthesis of 2‐aminopyrrolo[1,2‐b]pyridazines from 1,3‐diynamides and 1‐aminopyrroles via gold(I)‐catalyzed chemoselective hydroamination/hydroarylation cascade was described. 26 examples were conducted to explore the scope substrates. A plausible reaction mechanism also proposed. In addition, fluorescence properties both in solutions solid states resulting products investigated. magnified image

Язык: Английский

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Coinage metal carbenes in heterocyclic synthesis via formation of new carbon-heteroatom bonds

Tetrahedron, Год журнала: 2022, Номер 114, С. 132778 - 132778

Опубликована: Апрель 15, 2022

Язык: Английский

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Synthesis of acridinesviacopper-catalyzed amination/annulation cascades between arylboronic acids and anthranils

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(48), С. 9742 - 9745

Опубликована: Янв. 1, 2022

The direct conversion of aryl boronic acids and anthranils to acridines has been realized herein, via the catalysis copper species under acidic conditions.

Язык: Английский

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