Divergent Synthesis of Four Types of Fused N‐Containing Heterocycles via Oxidative Multi‐Component Cyclization Reaction

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

Опубликована: Янв. 31, 2025

Comprehensive Summary An atmospheric‐oxygen‐mediated four‐component reaction was developed for the divergent synthesis of pyrazolo[1,5‐ a ]pyrimidine and pyrazolo[3,4‐ b ]pyridine derivatives from readily available alcohols 3‐aminopyrazoles. In this transformation, atmospheric oxygen serves as green oxidant, promoting equivalent aldehydes four types N ‐containing heterocycles (> 40 examples). Remarkably, transformation features metal‐free molecular diversity.

Язык: Английский

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Synthesis of Benzoisochromene Derivatives via C–H Activation-Initiated Cascade Formal [4+2] and [2+4] Annulation of Aryl Enaminone with Vinyl-1,3-dioxolan-2-one

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 19, 2025

Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise effective synthesis benzoisochromene derivatives based on C-H activation-initiated cascade formal [4+2]/[2+4] aryl enaminone vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, acted as C4 synthon while vinyl-1,3-dioxolan-2-one C2 synthon. O-heterocycle, other hand, former latter C3O1 To our knowledge, this first simultaneous construction both carbocycle an O-heterocycle via concurrent C-H/C-N/C-O bond cleavage C-C/C-C/C-O formation. general, novel protocol features use readily obtainable substrates broad scope, excellent atom- step-economy, intriguing reaction pathway, valuable products.

Язык: Английский

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Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds

Organic Letters, Год журнала: 2024, Номер 26(12), С. 2511 - 2516

Опубликована: Март 20, 2024

This work demonstrates the synthesis of a variety perfluoroalkyl heterocycles via visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/SNV-type/cyclization sequences follow radical addition reaction diazoester, which differs from current role diazoesters as precursors/acceptors. transformation excellent functional group compatibility and allows for modification many bioactive molecules with diazoesters. Such could represent novel approach to photochemical diazo compounds.

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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Visible-light-induced C–S bond formation of pyrazolin-5-ones with thioureas to pyrazol-4-yl carbamimidothioates

Molecular Catalysis, Год журнала: 2025, Номер 580, С. 115086 - 115086

Опубликована: Апрель 8, 2025

Язык: Английский

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Photo-induced aerobic cross-coupling of quinoxalin-2(1H)-ones with electron-rich thiophenes

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

Опубликована: Янв. 1, 2025

Herein, an efficient aerobic cross-coupling of quinoxazolines with electron-rich thiophenes was presented. It's easy and effective access to 3-thiophenyl quinoxalinones without external photo-catalyst or transition-metal catalyst.

Язык: Английский

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Sodium Iodide-Promoted Construction of Fully Substituted 4-Sulfenyl-5-aminopyrazole Derivatives

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

Опубликована: Май 21, 2025

Transition-metal-free synthesis of diversely substituted 4-sulfenyl-5-aminopyrazoles was developed under mild conditions through NaI-mediated three-component reaction β-ketonitriles, disulfides, and hydrazines. The pyrazole products were constructed via consecutive cleavage C-O S-S bonds recombination C-N C-S bonds. methodology features broad substrate scope, transition-metal-free conditions, easy manipulation.

Язык: Английский

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Direct ortho‐Selective Amination of Naphthols with Nitroarenes through Transfer‐Hydrogenation

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(13)

Опубликована: Фев. 26, 2024

Abstract Hydrogen atom transfer from commonly used solvents to nitroarenes occurred. Such required C(sp 3 )H‐C(sp )H bond adjacent oxygen atoms, such as 1,4‐dioxane, tetrahydrofuran, alkanol, ethylene glycol, glycerol and bis(2‐methoxyethyl) ether. The transformation was transition‐metal free the reduced were trapped by naphthols their analogues at ortho ‐position. protocol provided a favourable efficient route access ‐arylaminonaphthols possible mechanism is depicted.

Язык: Английский

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Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Май 27, 2024

Abstract Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field synthetic chemistry has prioritized these directing considerable research endeavour toward developing efficient concise methodologies for their synthesis. Consequently, there is growing interest pioneering novel approaches to fabricate immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, environmental sustainability. This review sheds light on advancements utilization collective such methanol (alongside other alcohols), N,N ‐dimethylethanolamine (DMEA), triethylamine (TEA) (in conjunction with amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF) C1 synthons, serving foundational units synthesis N ‐heterocycles, quinazolinone, quinazoline, quinoxaline, pyridine, pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, or reagents, reported literature, have been explored.

Язык: Английский

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Regioselective Annulation of 3(5)‐Aminopyrazole with Aryl Ketones or Aryl Alkynes Using <i>N</i>,<i>N</i>‐Dimethylethanolamine as a Single/Triple Carbon Synthon

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3591 - 3596

Опубликована: Июнь 19, 2024

Abstract An efficient and regioselective cyclization for construction of pyrazolo[3,4‐ b ]pyridines methylene‐bridged bis(pyrazolo[1,5‐ a ]pyrimidines) has been established. It involves [3+2+1] annulation 3(5)‐aminopyrazole, N,N ‐dimethylethanolamine (DMEA), with 1,2‐insertion aryl methyl ketones or 2,1‐insertion alkynes. DMEA is oxidized through C( sp 3 )‐H activation to provide single triple carbon source.

Язык: Английский

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