C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2324 - 2338

Опубликована: Янв. 1, 2024

This review summarizes the most recent progress made in C–H bond activation-initiated spiroannulation reactions and their applications construction of structurally diverse biologically valuable spirocyclic scaffolds.

Язык: Английский

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Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(15), С. 2916 - 2947

Опубликована: Янв. 1, 2024

In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.

Язык: Английский

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Metal-free construction of dihydropyrazino[2,3-b]indoles from 2-aminoacetophenones, isocyanates and 1,2-diamines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(10), С. 2043 - 2048

Опубликована: Янв. 1, 2024

A Brønsted acid/iodine co-mediated approach to construct dihydropyrazino[2,3-

Язык: Английский

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Synthesis of structurally diverse pyrazolo[1,2-a]pyrazolones based on the selective C–H bond alkenylation–annulation of 1-arylpyrazolidinones with allenyl acetates

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3874 - 3880

Опубликована: Янв. 1, 2024

Presented herein is a concise synthesis of diverse pyrazolo[1,2- ]pyrazolones based on condition-controlled divergent reactions 1-arylpyrazolidinones with allenyl acetates.

Язык: Английский

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Synthesis of pyrazolo[1,2-a]cinnolinone via copper-catalyzed 6-endo-dig cyclization

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134593 - 134593

Опубликована: Март 1, 2025

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Rh(III)‐Catalyzed C−H Activation/O‐Annulation for Construction of Divergent Spirosuccinimide and Maleimide‐Fused Isochromenes

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(22), С. 3915 - 3926

Опубликована: Сен. 12, 2023

Abstract A rhodium‐catalyzed [5+1] cycloaddition via C−H activation/ O ‐annulation strategy for synthesizing biologically interesting isochromenes is presented. This protocol selectively provides divergently functionalized containing spirosuccinimide and maleimide scaffolds according to the maleimides itaconimides used as substrates. methodology exhibits an extensive substrate scope, remarkable functional group tolerance, high regioselectivity.

Язык: Английский

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Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1840 - 1846

Опубликована: Фев. 8, 2024

Abstract Herein, we report a chemo‐ and regioselective Rh‐catalyzed redox C7‐spiroannulation reaction of N ‐benzo[ d ]imidazole indolines with maleimides, resulting in series indoline fused azaspirocycles up to 92% yield. The synthetic utility is demonstrated by the synthesis highly functionalized nitrogen‐containing spiropolycyclic skeletons. annulation could also be performed maleic esters acrylates. products were purified simple filtration. Rh catalyst can recycled, at gram‐scale using 0.5 mol% catalyst, which makes this protocol potentially applicable industry. Moreover, efficient post‐modification pharmaceutical molecules demonstrates its practicability.

Язык: Английский

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Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Март 20, 2024

Abstract We report herein a palladium‐catalyzed, site‐selective cyclative annulation of o ‐alkynyl arylamides with maleimide for the stereoselective construction succinimide‐fused benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, downstream transformations. Control labeling experiments were conducted get insights into mechanism.

Язык: Английский

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Cascade [4 + 1] Annulation through Activation of the C(sp²)–H Bond Enabling Benzothiadiazinoisoindolcarboxylate, Benzothiadiazinoisoindole, and Benzothiadiazinoisoindolepyrrolidinedione as Hybrid Spiro-Heterocyclic Frameworks

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7705 - 7717

Опубликована: Май 17, 2024

Two structurally distinct and biologically privileged succinimide isoindole heteroarenes bearing benzothiadiazinedioxide motif-centered hybrid conjugates are proficiently achieved through Rh(III)-catalyzed sequential C(sp

Язык: Английский

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Diastereoselective Intramolecular Spirocyclization via C(sp3)‐H Bond Functionalization Towards the Synthesis of 2,7‐Diazaspiro[4.5]decane‐1,3‐diones

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 29, 2024

Abstract The C( sp 3 )−H functionalization via intramolecular hydride transfer initiated cascade annulation for the synthesis of spiro‐fused succinimide‐containing tetrahydroquinolines induced by iminium intermediates is described. A series diastereoselective 2,7‐diazaspiro[4.5]decanes‐1,3‐diones were achieved using ortho ‐amino‐benzylidene‐succinimide Lewis acid catalysis. This scandium triflate Sc(OTf) catalysed, oxidant‐free protocol leads to a class derivatives with 48–98% yield in single step.

Язык: Английский

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