Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

Carboxylic acids are bench-stable and readily available chemical feedstocks that function as optimal fundamental synthetic platforms for the construction of C(sp3)–C(sp3) bonds via decarboxylation processes. We present a novel practical protocol decarboxylative alkylation Morita–Baylis–Hillman acetates with various carboxylic photoinduced iron-mediated ligand-to-metal charge transfer (LMCT) process under redox-neutral conditions. This method exhibits remarkable tolerance to wide array acids, including primary, secondary, tertiary obviating requirement preactivated radical precursors. The preliminary mechanistic analyses indicate pathway is involved in this catalytic transformation.

Language: Английский

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N-Arylpyrazole based Scaffolds: Synthesis and biological applications

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(3), P. 101861 - 101861

Published: April 24, 2024

N-aryl pyrazoles are important building blocks in many biologically active compounds, natural products, pharmaceuticals, and industries. It is an moiety of various drugs exhibits extensive biological activities viz., antibiotic, anticancer, antifungal, anti-inflammatory, anti-coagulant, analgesic, antipyretic, anti-depressant, insecticidal, hyperglycemic activities. Various protocols have been designed for the synthesis facilitated by a wide variety metal-based catalysts at high or room temperature, metal free reactions, named multicomponent those occurring under different electromagnetic radiations. ligands found to promote Cu-catalyzed N-arylation pyrazole mild conditions short time. This review describes applications derivatives reported during 2019–2023.

Language: Английский

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A Base-dependent Switch in the Reactivity of Baylis–Hillman Ketones with Hydrazines: Access to N'-Alkyl Benzohydrazides and Fluorescent Dihydropyrazoles

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

MBH ketones react with hydrazines in the absence of a base to afford fluorescent dihydropyrazoles, whereas addition Et 3 N leads formation benzohydrazides. Novel pyrazole analogues could be obtained by oxidation dihydropyrazoles.

Language: Английский

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Green Light Triggered Radical Annulation for the Synthesis of Indenone by Metal‐Free Photocatalysis

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 23, 2024

Abstract Low‐energy light, endowing with excellent characteristics of lower energy, fewer side reactions, more abundance in solar light. The scenario has been developed for the fabrication indenone through a low‐energy green light driven radical annulation reaction between α‐keto acids and internal alkynes using Rhodamine 6G as photocatalyst. Various kinds substrates are suitable this methodology, affording corresponding indenones greener efficient manner.

Language: Английский

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Antibacterial and Antifungal Pyrazoles Based on Different Construction Strategies

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 282, P. 117081 - 117081

Published: Nov. 20, 2024

Language: Английский

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Chemoselective Intramolecular Morita–Baylis–Hillman Reaction; Acrylamide and Ketone as Sluggish Reacting Partners on a Labile Framework

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1073 - 1082

Published: Jan. 2, 2024

Chemoselectivity is an important issue frequently encountered while working over labile precursors. Carbonyl compounds with a heteroatom at the β carbon are sensitive precursors because they prone to elimination under different conditions. Morita-Baylis-Hillman (MBH) reaction, although widespread method for C-C bond formation, has its own limitations. Acrylamide and ketone such limitations of MBH reaction. Using them together intramolecular (IMBH) reaction on framework significant 2-fold synthetic challenge. A highly chemoselective IMBH been established using 1,4-diazabicyclo[2.2.2]octane (DABCO) as promoter. The protocol leads quick access diversely substituted functionalized piperidone in high yields. Various substitution patterns form 34 successful examples have studied. diastereoselective version tolerance various functional protecting groups added advantages developed methodology. tertiary position ketone, however, led complete reversal selectivity gave only product. Control experiments toward better understanding pattern, role catalyst, mechanistic study carried out. As application adduct, one-step allylic rearrangement dihydropyridone also demonstrated.

Language: Английский

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Overview of Phenylhydrazine‐Based Organic Transformations

ChemistrySelect, Journal Year: 2024, Volume and Issue: 10(1)

Published: Dec. 30, 2024

Abstract Phenylhydrazines, comprised of a phenyl group attached with hydrazine unit, contribute potentially to organic synthetic transformations. Because the myriad applications, last decade has witnessed considerable upsurge interest perform various reactions catalyzed/mediated/promoted by phenylhydrazines. Some these have shown high regioselectivity in short reaction time under mild conditions. The emergence innumerable transformations utilizing phenylhydrazine unleashed numerous openings for development diverse heterocyclic scaffolds. Given importance this valuable chemical entity, review highlights methodologies Moreover, present article will considerably synthesis as well pharmaceutical chemistry. Academically, be interesting and informative researchers attempting develop new routes structures.

Language: Английский

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