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

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2665 - 2692

Published: Jan. 1, 2024

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

Language: 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, Journal Year: 2023, Volume and Issue: 25(12), P. 2139 - 2144

Published: March 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]

Language: Английский

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

RSC Advances, Journal Year: 2024, Volume and Issue: 14(9), P. 5817 - 5845

Published: Jan. 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.

Language: 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, Journal Year: 2024, Volume and Issue: 48(17), P. 7614 - 7638

Published: Jan. 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.

Language: 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, Journal Year: 2023, Volume and Issue: 10(19), P. 4843 - 4847

Published: Jan. 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.

Language: Английский

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

Topics in Current Chemistry, Journal Year: 2022, Volume and Issue: 380(6)

Published: Oct. 28, 2022

Language: Английский

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

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1348 - 1355

Published: Jan. 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.

Language: Английский

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

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(3)

Published: Jan. 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.

Language: 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, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: 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, Journal Year: 2024, Volume and Issue: 89(9), P. 6456 - 6464

Published: April 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.

Language: Английский

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