Electrochemical C–H Alkylation of Azauracils Using N-(Acyloxy)phthalimides

Organic Letters, Год журнала: 2024, Номер 26(34), С. 7227 - 7232

Опубликована: Авг. 20, 2024

We present an electrochemical alkylation of azauracils using N-(acyloxy)phthalimides (NHPI esters) as readily available alkyl radical progenitors under metal- and additive-free conditions. Several are shown to undergo with array NHPI esters (1°, 2°, 3°, sterically congested), providing the desired products in good excellent yields. This operationally simple method is robust, scalable, suitable for both batch flow setups.

Язык: Английский

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Arenethiolate-Catalyzed 1,5-HAT of Aryl Halides: Synthesis of γ-Spirolactams

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3081 - 3085

Опубликована: Апрель 3, 2024

γ-Spirolactam is a privileged building block that found in wide range of natural products and bioactive compounds. Herein, we report an arenethiolate-catalyzed 1,5-HAT aryl halides to obtain γ-spirolactams through SET reduction/intramolecular 1,5-HAT/cyclization/HAT process. This protocol features metal-free conditions broad substrate scope, furnishing the moderate excellent yields. Notably, bromides, chlorides even fluorides are well tolerated this transformation. A mechanism involving arenethiolate as catalyst proposed based on DFT calculation.

Язык: Английский

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Recent advances in post Ugi-4CR dearomatizations for constructing spiro heterocycles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4895 - 4912

Опубликована: Янв. 1, 2024

This review summarizes recent advances in the combination of Ugi-4CR and dearomatization for synthesis spirocycles.

Язык: Английский

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A highly diastereoselective one-pot Ugi/radical spirocyclization/aza-Michael addition sequence

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(19), С. 3887 - 3892

Опубликована: Янв. 1, 2024

Highly diastereoselective sequence consisting of eosin-Y catalyzed radical spirocyclization post-Ugi adducts with aryl thiols or diselenides followed by aza-Michael addition provided access to complex azaspirotricycles in an efficient manner.

Язык: Английский

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One-Pot Regioselective Synthesis of Spiroimidazolidinones via a Sequential Ugi 4CR/Azide-Isocyanide Coupling/Cyclization/Rearrangement/Hydroxylation Reaction

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 24, 2025

Herein a novel and robust methodology to spiroimidazolidinones has been developed under mild reaction. The reaction of (Z)-2-azido-3-phenylacrylic acids 1, aldehydes 2, amines 3, isocyanides 4, 6 produced regioselectively in 71–88% yields via sequential Ugi 4CR/Pd(0) catalyzed azide-isocyanide coupling/cyclization/rearrangement/hydroxylation Furthermore, the easily accessible starting materials, high bond-forming efficiency, broad substituent tolerance make this strategy useful synthetic medicinal chemistry.

Язык: Английский

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A Domino Decarboxylative Alkylation/Annulation for the Synthesis of Pyrrolo-benzimidazolones

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

The reaction of N -propiolyl-benzimidazole with aliphatic carboxylic acids in the presence ammonium persulfate leading to pyrrolo-benzimidazolones is presented.

Язык: Английский

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Electrochemical selenylative ipso-Annulation of N-benzylacrylamides to seleno-azaspiro[4.5]decadienones

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(30), С. 6141 - 6148

Опубликована: Янв. 1, 2024

Construction of seleno azaspiro[4.5]decadienones using an electrochemical approach is achieved via domino selenylation/ ipso -annulation.

Язык: Английский

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One-Pot and Mild Synthesis of Novel Antibacterial 3-(1,3,4-Oxadiazol-2-yl)isoindolin-1-ones via On-Step Four-Component Dicyclization Reaction

Authorea (Authorea), Год журнала: 2024, Номер unknown

Опубликована: Янв. 30, 2024

A novel and efficient four-component dicyclization strategy has been developed for one-step constructing diverse antibacterial 3-(1,3,4-oxadiazol-2-yl)isoindolin-1-ones under very mild base-free metal-free conditions without other additives. This one-pot process underwent two consecutive cyclization reactions including tandem Ugi/aza-Wittig reaction N-acylation by utilizing (N-isocyanimine)triphenylphosphorane, methyl 2-formylbenzoate, primary amines, carboxylic acids. The method was conferred its favorable characteristics, ambient temperature conditions, synthesis, any additives, facile gram-scale good yields.

Язык: Английский

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Electrochemical Synthesis of Phosphorylated Azaspiro[4.5]di/trienones through Dearomative Spirocyclization

Chemical Communications, Год журнала: 2024, Номер 60(57), С. 7351 - 7354

Опубликована: Янв. 1, 2024

Cp 2 Fe-mediated electrochemical synthesis of a diverse array phosphorylated azaspiro[4.5]di/trienones has been developed, which demonstrated broad substrate scope and good diastereoselectivity.

Язык: Английский

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An entry to spiro-fused sultams via electrochemical brominative ipso-annulation of N-aryl alkynyl sulphonamides

Tetrahedron Letters, Год журнала: 2024, Номер unknown, С. 155330 - 155330

Опубликована: Окт. 1, 2024

Язык: Английский

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