2-Methyl-4-Oxo-4,5-Dihydro-1H-Pyrrole-3-Carboxylic Acid Phenylamide DOI Creative Commons
Plamen Angelov, Pavel Yanev

Molbank, Journal Year: 2024, Volume and Issue: 2024(1), P. M1778 - M1778

Published: Feb. 28, 2024

2-Methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid phenylamide was obtained as a single product in an experiment on the cyclization modes of glycine-derived enamino amide. High yield and operational simplicity are main features presented synthetic procedure. Additionally, this result extends our previous observations reactions similarly functionalized enamines, by revealing preferred pathway under Boc-deprotection conditions.

Language: Английский

Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations DOI
Dongsheng Yang, Xiang‐Long Chen, An‐Xin Wu

et al.

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

Citations

20
Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity DOI
Wenli Song, Yunyun Liu, Nan Yan

et al.

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

Citations

41
I2/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis DOI Creative Commons

Rakshanda Singhal,

Satya Prakash Choudhary,

Babita Malik

et al.

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

Citations

17
Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation DOI
Swadhin Swaraj Acharya,

Sagarika Patra,

Liza Mama Barad

et al.

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

Citations

12
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 DOI

Shuang‐Gui Lei,

You Zhou, Li‐Sheng Wang

et al.

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

Citations

18
Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry DOI
Hao Lü, Tong Zhou, Lifen Peng

et al.

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

Published: Oct. 28, 2022

Language: Английский

Citations

29
FeCl3/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives DOI

Song Yingchun,

Ming‐Xuan Wang,

Yun‐Ying Yi

et al.

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

Citations

4
Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles DOI
Anup Sharma,

Mahesh Kumar,

Shiv Chand

et al.

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

Citations

0
Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis DOI
Reetu Reetu,

Sangita Kalita,

Sonali Prava Dash

et al.

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

Citations

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

Chahui Du

et al.

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

Citations

2