Cu₂O-catalyzed cascade phosphinylation/cyclization of 2′-aminochalcones for the synthesis of hemi-indigo derivatives

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(21), С. 4249 - 4253

Опубликована: Янв. 1, 2024

A Cu

Язык: Английский

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A Novel Ring-Opening/Ring-Closing Cascade Reaction Selectively Induced by Aliphatic Primary Amine Using Phenolic Hydroxyl as a Traceless Directing Group

Synthesis, Год журнала: 2023, Номер 55(09), С. 1441 - 1450

Опубликована: Янв. 12, 2023

Abstract An interesting ring-closing/ring-opening cascade reaction selectively induced by aliphatic primary amine for the synthesis of functionalized aminomaleimides is described. This work features phenolic hydroxyl as a traceless directing group that forms critical six-membered intermediate and then lactone ammonolysis/intramolecular amidation sequence. two-step, one-pot practical protocol has broad substrate scope (39 examples) delivers structurally diverse in good to excellent yields.

Язык: Английский

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Recent progress in the direct phosphorylation of parent heterocycles to construct phosphorylated heterocycles

Chemistry of Heterocyclic Compounds, Год журнала: 2023, Номер 59(4-5), С. 193 - 200

Опубликована: Май 1, 2023

Язык: Английский

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Multicomponent Reactions between Heteroatom Compounds and Unsaturated Compounds in Radical Reactions

Molecules, Год журнала: 2023, Номер 28(17), С. 6356 - 6356

Опубликована: Авг. 30, 2023

In this mini-review, we present our concepts for designing multicomponent reactions with reference to a series of sequential radical that have developed. Radical are well suited the design due their high functional group tolerance and low solvent sensitivity. We focused on photolysis interelement compounds heteroatom–heteroatom single bond, which readily generates heteroatom-centered radicals, studied photoinduced addition unsaturated compounds. First, background is described, basic methodology construction explained. Next, examples involving two one compound presented, as Furthermore, intramolecular cyclization processes described.

Язык: Английский

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NBS-Promoted Synthesis of Thiocyanated Aminomaleimides and Site-Selective Intramolecular Cyclization Access to 1,4-Benzothiazepines via S–CN Bond Cleavage

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5266 - 5276

Опубликована: Апрель 9, 2024

A transition metal-free concise and efficient protocol for the synthesis of thiocyanated aminomaleimides benzo[e][1,4]thiazepine derivatives has been developed. The method involves an initial α-C–H thiocyanation with KSCN TEMPO-mediated tandem S–CN bond cleavage/intramolecular cyclization substitution processes, which enables formation seven-membered S/N-heterocycles. This synthetic strategy provides a reliable biologically interesting by using as sulfur sources well expands application enaminones reactions in heterocycles synthesis.

Язык: Английский

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Copper‐Catalyzed One‐Pot Three‐Component Aminophosphinoylation of 1,4‐Naphthoquinone

ChemistrySelect, Год журнала: 2024, Номер 9(27)

Опубликована: Июль 12, 2024

Abstract A copper‐catalyzed one‐pot three‐component aminophosphinoylation reaction of 1,4‐naphthoquinone with disubstituted phosphine oxides and arylamines has been developed. Various diverse structures electronic properties can work smoothly 1,4‐naphthoquinone, afforded a series corresponding aminophosphinoylated 1,4‐naphthoquinones up to 96 % isolated yield. The present method features easily available reagents, operational simplicity, broad substrate scope, high atom step economy. potential practicality this protocol was further demonstrated by gram‐scale synthesis.

Язык: Английский

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Eco-Friendly alpha,beta-C(sp3)-H Difunctionalization of Tertiary Amines via Sequential [1,5]-Hydride Transfer and Hetero-Diels-Alder Cyclization

Chemical Communications, Год журнала: 2024, Номер 60(77), С. 10712 - 10715

Опубликована: Янв. 1, 2024

An unprecedented eco-friendly multi-component domino reaction for the synthesis of novel

Язык: Английский

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Cu‐Catalyzed C(sp²)−H Bond Aminosulfonylation of Maleimides

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(15), С. 2530 - 2535

Опубликована: Июль 13, 2023

Abstract A copper‐catalyzed direct C( sp 2 )−H bond aminosulfonylation of maleimides is demonstrated. This protocol enables concurrent construction )−N and )−SO bonds in one‐step features high efficiency, broad substrate scopes, good functional‐group tolerance, mild reaction conditions. Preliminary mechanistic studies indicate that the probably involves a radical way. Significantly, this method applicable to synthesize derivatives pharmaceuticals such as Desloratadine, Fluoxetine, Atomoxetine, Maprotiline.

Язык: Английский

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Isocyanide‐Based One‐Pot Cascade Synthesis of 3‐Acyl Isoindolinones^†

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(3), С. 259 - 263

Опубликована: Сен. 21, 2023

Comprehensive Summary A series of 3‐acyl‐substituted isoindolinone derivatives were synthesized in a one‐pot manner via the reaction o ‐bromobenzaldehydes, isocyanides, and carboxylic acids presence palladium catalyst base. The employing easily available starting materials features simple operation high efficiency. mechanistic study showed that might undergo 1) Pd‐catalyzed [3+2] cyclization ‐bromobenzaldehyde with isocyanide re‐insertion another molecule isocyanide, 2) addition acid to situ formed ketenimine followed by rearrangement relay give 3,3‐diacyl‐substituted derivative. Further transformations obtained products through decarbonylation could also be realized.

Язык: Английский

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Synthesis, Characterization and Biological Evaluation of 3‐Oxo‐pyrimido[1,2‐b]indazoles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(19), С. 4055 - 4060

Опубликована: Июль 20, 2024

Abstract The synthesis of substituted 3‐oxo‐pyrimido[1,2‐ b ]indazoles from 3‐aminoindazoles and ketones has been established. It involves one molecule two molecules via a [3+2+1] three‐component annulation process. 3‐Oxo‐pyrimido[1,2‐b]indazoles exhibit strong yellow fluorescence in various solvents. A wide range products have anti‐oxidant activities. Cytotoxicity studies indicate that compounds 3 , aa ab obvious effects on both HCT116 A549 cancer cell lines.

Язык: Английский

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