Review of application of the I₂ and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2665 - 2692

Опубликована: Янв. 1, 2024

The synthesis of small molecules and complex scaffolds is one the most important topics in organic synthesis.

Язык: Английский

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Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity

Organic Letters, Год журнала: 2023, Номер 25(12), С. 2139 - 2144

Опубликована: Март 22, 2023

The three-component reactions of enaminones, α-diazo esters/ketones, and t-butyl nitrite (TBN) for the switchable synthesis isomeric isoxazoles have been realized. catalysis with Cu(II) salt provides 3,4-disubsituted via [3 + 2] cycloaddition. On other hand, Ag(I) identical substrates leads to reversed C3 C4 substitution based on a key [2 1]

Язык: Английский

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I₂/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

RSC Advances, Год журнала: 2024, Номер 14(9), С. 5817 - 5845

Опубликована: Янв. 1, 2024

A variety of bioactive compounds can be synthesized via C–C and C–X (X = O/S/N/Se/Cl/Br) bond formation using an efficient catalytic system I 2 /DMSO. This review highlights the progress identifies potential paths for future research in this field.

Язык: Английский

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Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

New Journal of Chemistry, Год журнала: 2024, Номер 48(17), С. 7614 - 7638

Опубликована: Янв. 1, 2024

In the iodine–DMSO medium, methyl group of azaarenes is converted into aldehyde via Kornblum oxidation and trapped in situ by nucleophiles to create azaarene-linked functionalized scaffolds.

Язык: Английский

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I₂-DMSO mediated dual α,β-C(sp²)–H functionalization/bicyclization of o-hydroxyphenyl enaminones to construct C2,C3-disubstituted chromone derivatives: chromeno[2,3-b]pyrrol-4(1H)-ones

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4843 - 4847

Опубликована: Янв. 1, 2023

An unprecedented dual α,β-C(sp 2 )–H functionalization/bicyclization strategy of o -hydroxyphenyl enaminones for the preparation chromeno[2,3- b ]pyrrol-4(1 H )-ones has been established.

Язык: Английский

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Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Topics in Current Chemistry, Год журнала: 2022, Номер 380(6)

Опубликована: Окт. 28, 2022

Язык: Английский

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FeCl₃/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1348 - 1355

Опубликована: Янв. 13, 2024

Abstract A total synthesis strategy was developed for the of luotonin A, B and their analogues using synergistic FeCl 3 /KI‐catalyzed oxidative cyclization. This protocol utilizes cheap widely available N ‐propargyl 2‐methyl‐quinazolinones arylamines under mild conditions, it has a wide substrate scope high atom economy. Different natural products (luotonin derivatives) can be synthesized via unique switchable approach. Further transformations from to E structural modification demonstrate potential applications this method. Moreover, camptothecin also modified with reported afford hydroxyl‐substituted product.

Язык: Английский

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Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

ChemistrySelect, Год журнала: 2024, Номер 9(3)

Опубликована: Янв. 17, 2024

Abstract Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis use iodine DMSO in various synthetic routes for preparation valuable targets presented. These reduce acceptance on expensive additives reagents, offer more sustainable solution these scaffolds.

Язык: Английский

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Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles

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

Опубликована: Март 11, 2025

A new approach to multifunctionalized pyrroles has been explored by the tandem cyclization of α-oxoketene-N,S-acetals with β-ketodinitriles using Cu(MeCN)4BF4 and Ag2CO3 in toluene under reflux conditions. The reaction involves C–C/C–N bond creation, is assumed proceed via enamine formation, intramolecular cyclization, rearrangement. potential methodology also demonstrated for a gram-scale as well some useful organic transformations. offers practical pathway achieve polysubstituted broad substrate scope good functional group tolerance.

Язык: Английский

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Iodine-Catalyzed Diversity-Oriented Synthesis of 3,4-Heterocycle-Fused Coumarins from 4-Aminocoumarins and Aurones in Different Solvent

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6456 - 6464

Опубликована: Апрель 15, 2024

An unprecedented protocol has been developed for the synthesis of 3,4-heterocycle-fused coumarins from 4-aminocoumarins and aurones through iodine-catalyzed cascade reactions. Dihydropyridine-fused coumarin, pyridine-fused pyrrole-fused coumarin derivatives were achieved in good yields with high selectivity when CH3CN, AcOH, DMSO used as solvent, respectively. This provides several advantages, such easily available starting materials, atom economy, friendly environment, simple procedure.

Язык: Английский

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