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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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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Copper‐catalyzed radical‐induced annulation‐halo(bi)cyanomethylation of indole‐tethered 1,6‐enynes toward pyrrolo[1,2‐a]indoles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3578 - 3584

Опубликована: Июнь 18, 2024

Abstract A copper‐catalyzed radical‐induced annulation‐halocyanomethylation of indole‐linked 1,6‐enynes has been established using haloacetonitrile as radical precursors, enabling the synthesis 21 cyanomethylated pyrrolo[1,2‐ a ]indoles with yields ranging from 42% to 81% and Z / E ratio up 19:1. Moreover, by adjusting reaction temperature, variation annulation‐bromobicyanomethylation process was achieved, resulting in production 12 bicyanomethylated ]indole isomers 41–68%. The stereoisomeric mixture products could be purified their pure configurations through recrystallization. proposed mechanism formulated series control experiments.

Язык: Английский

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I₂-Induced Metal-Free C(sp²)–H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1H-indoles

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

Опубликована: Апрель 3, 2025

The I2-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with indoles and subsequent treatment K2CO3 provided (benzofuran-3-yl)-1H-indoles in good to excellent yields high regioselectivity. This one-pot two-step strategy proved be suitable for a wide range substrates except aliphatic alkynyl as well the bearing N-protected groups such Ts group possessing strong electron-withdrawing feature. procedure involved cross-coupling construction benzofuran framework via 5-exo-dig cyclization.

Язык: Английский

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Mn(I)‐NNSe Pincer Complex Catalyzed Regioselective Synthesis of Bisindolylmethanes under Base and Solvent‐Free Conditions

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

Опубликована: Май 23, 2025

Abstract Here, we present a catalytic, regioselective synthesis of bisindolylmethanes through the reaction indoles and benzyl alcohol derivatives mediated by metal‐ligand cooperative catalysis. The is catalyzed an earth‐abundant manganese‐NNSe pincer complex without need for base, solvent, additives, or hydrogen acceptors yielding water dihydrogen as environmentally friendly by‐products. Notably, C‐3 N ‐alkylation indole, commonly observed in similar reactions were not detected. Mechanistic studies suggest that catalysis Mn(I)‐NNSe initiates conversion to benzaldehyde elimination, which subsequently facilitates bisindolylmethane derivatives. To highlight practical utility this method, wide range substrates can be activated with low catalyst loading under mild conditions.

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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Photocatalytic Tandem Protocol for the Synthesis of Bis(indolyl)methanes using Cu-g-C₃N₄–Imine Decorated on TiO₂ Nanoparticles under Visible Light Irradiation

ACS Omega, Год журнала: 2024, Номер 9(29), С. 31344 - 31352

Опубликована: Июль 11, 2024

In this article, the visible-light-assisted photocatalytic activity of TiO2 nanoparticles functionalized with Cu(II) g–C3N4–imine was exploited for aerobic oxidation alcohols to aldehydes followed by condensation indoles in presence 2,2,6,6-tetramethylpiperidinyloxy present a one-pot tandem strategy synthesis bis(indolyl)methanes (BIMs) under solvent-free conditions. The synergistic effect between components improve as-prepared Cu-g-C3N4–imine/TiO2 resulting from electron–hole separation approved PL spectroscopy. Moreover, action spectra showed light-dependent photocatalysis effective visible-light responsivity photocatalyst. method includes different aspects green chemistry: variety BIMs using that are less toxic, more available, economical, and stable than aldehydes; removing byproducts overoxidation polymerization indoles; use air as safe oxidant; visible light energy source; A reusability test demonstrated catalyst retained its efficiency even after five runs.

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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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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Advances in Self-Organized Total Synthesis of Natural Products

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

In this review, we account for the definition, delimitation, and categorization of self-organized total synthesis then elucidate a comprehensive understanding synthetic strategy based on our intensive explorations.

Язык: Английский

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