I₂–DMSO mediated multicomponent convergent synthesis of imidazo[2,1-a]isoquinoline derivatives via a triple in situ cross-trapping strategy

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(16), С. 4080 - 4085

Опубликована: Янв. 1, 2023

An I 2 –DMSO mediated one-pot approach to imidazo[2,1- a ]isoquinoline derivatives from readily available aryl methyl ketones and isoquinolin-1-amine has been demonstrated.

Язык: Английский

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The Cascade Reaction Chemistry of Diazo Compounds with Intentionally Designed Alkene to Access Esterified Heterocycles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

Exploration of the cascade reactivity diazo compounds with alkenes is a challenging and largely unmet goal. Herein, we disclose light-mediated de novo synthesis esterified heterocycles under mild conditions. The reaction displays broad functional group tolerance, including wide variety alkenes, compounds, some bioactive molecules. Importantly, synthetic appeal was demonstrated for synthesizing indoleamine 2,3-dioxygenase inhibitor analogue, deethylated derivative natural product leucomidine C, anti-inflammatory agent AN669.

Язык: Английский

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Sustainable Synthesis of Polyfluoro-Pyrimido [1,2-a] Benzimidazole Derivatives Using a Tandem Strategy─Ultrasound and an Integrated Continuous Flow System

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 6, 2025

We have developed a novel ultrasound technique that generates significant amounts of CF3-substituted benzo[4,5] imidazo [1,2-a]pyrimidine analogues from easily accessible starting materials in an ecologically friendly and efficient approach. This method is notably helpful for producing physiologically relevant compounds containing the imidazopyrimidine unit, which serves as versatile building block synthesis N-fused heterocycles devoid metals, solvents, additives, catalysts. Additionally, utilizing open-air environment, range polyfluoro-ynones were successfully reacted with 2-aminobenzimidazole, generating diverse array polyfluoroimidazo[1,2-a]pyrimidine derivatives. Furthermore, by employing integrated flow system approach, we able to synthesize polyfluoro-substituted benzo[4,5]imidazo[1,2-a]pyrimidine derivatives alkynes much shorter reaction time. Gram-scale proved this method's scalability highlighted its potential synthetic industrial applications. The straightforward nature process, broad compatibility various functional groups, substantial sustainability advantages collectively underscore significance.

Язык: Английский

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Photocatalytic Synthesis of Isoquinolinediones via the Cascade Reaction of N-Alkyl-N-methylacrylamides with Diazo Compounds

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 25, 2025

Carbon radicals generated from acceptor diazo compounds prefer to add electron-rich olefins and heteroarenes due their containing electron-withdrawing groups. Herein, a cascade reaction of with electron-deficient is developed. In the presence visible light Ru catalyst, generate carbon via proton-coupled electron transfer process, followed by addition various N-alkyl-N-methylacrylamides subsequent cyclization give series acyl-substituted isoquinolinediones.

Язык: Английский

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Condition‐Controlled Selective Synthesis of CF₃‐Chromene and CF₃‐Benzofuran from N‐Phenoxyacetamide and CF₃‐Ynone

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Язык: Английский

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