Recent Advances for the Transformation of Maleimides via Annulation DOI
Mohammad Aslam, Muhammad Saeed Akhtar, Hee Nam Lim

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This review highlights recent advances in maleimide-based annulation and cyclization strategies, offering insights into their synthetic versatility potential applications creating structurally diverse aromatics bioactive heterocycles.

Language: Английский

Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation DOI
Swadhin Swaraj Acharya,

Sagarika Patra,

Rojalini Maharana

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(15), P. 2916 - 2947

Published: Jan. 1, 2024

In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.

Language: Английский

Citations

15
Palladium-Catalyzed Aerobic Oxidative Spirocyclization of Alkyl Amides with Maleimides via β-C(sp3)–H Activation DOI
Ananya Dutta, Masilamani Jeganmohan

Organic Letters, Journal Year: 2023, Volume and Issue: 25(34), P. 6305 - 6310

Published: Aug. 22, 2023

An efficient method for the synthesis of bicyclic spirodiamine molecules via β-C(sp3)–H bond activation aliphatic amides, followed by cyclization with maleimides, has been developed. The reaction proceeds through an amide-directed alkyl amides and subsequent maleimides. methodology is highly compatible a wide variety Amides derived from biologically active fatty acids were also found to be protocol. A palladacycle was synthesized intermediate in this reaction. plausible mechanism proposed account spirocyclization.

Language: Английский

Citations

14
Unusual Regioselective C–H Difluoroalkylation of Heteroarenes under Photoredox Catalysis DOI

Sudip Laru,

Sourav Ghoshal, Pranab Sarkar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5098 - 5104

Published: June 7, 2024

We disclose a new general strategy for the site-selective difluoroalkylation of nonprefunctionalized heteroarenes, such as quinoxaline at C-8 position, and benzothiadiazole, benzoxadiazole, benzothiazole C-4 position via consecutive organophotoredox-catalyzed radical–radical cross-coupling base-assisted hydrogen abstraction reactions. The current methodology represents direct difluoroalkylative to allow broad functional group tolerance wide substrate scope in good excellent yields. Careful experimental investigations detailed DFT calculations revealed exact site-selectivity heteroarenes possible mechanistic pathway.

Language: Английский

Citations

4
Photo-induced 1,2-thiohydroxylation of maleimide involving disulfide and singlet oxygen DOI
Tamanna Khandelia, Subhendu Ghosh, Pritishree Panigrahi

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(75), P. 11196 - 11199

Published: Jan. 1, 2023

A visible light-driven di-functionalization of maleimide with disulfide and in situ -generated singlet oxygen offers selective 1,2-thiohydroxylation under additive-free conditions.

Language: Английский

Citations

9
Photo‐Induced Generation of Oxygenated Quaternary Centers via EnT Enabled Singlet O2 Addition to C3‐Maleimidated Quinoxaline: A Reagent‐Less Approach DOI
Subhendu Ghosh, Tamanna Khandelia, Anjali Mahadevan

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(45)

Published: May 8, 2024

Demonstrated here is an external photo-sensitizer-free (auto-sensitized) singlet oxygen-enabled solvent-dependent tertiary hydroxylation and aryl-alkyl spiro-etherification of C3-maleimidated quinoxalines. Such "reagent-less" photo-oxygenation at Csp

Language: Английский

Citations

3
Palladium-Catalysed Spiro-Cyclisation of Substituted Amino Acids with Maleimides via γ-C(sp3)–H Bond Activation DOI

Trisha Chakraborty,

Masilamani Jeganmohan

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Achieving the site-selective functionalization of unactivated C(sp3)-H bonds remains a major challenge in organic synthesis. Herein, we report an efficient method for synthesis spiro pyrrolidine molecules via γ-C(sp3)-H bond activation substituted amino acids. A variety acid and alcohol derivatives, as well dipeptides, were functionalized using this method. Also, spirocyclization optically active substrates provided potential route preparing separable diastereomers pure enantiomeric form. Moreover, some mechanistic insights have been conducted to propose feasible reaction mechanism present reaction.

Language: Английский

Citations

0
Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles DOI

Jinfang Zhao,

Chao Pi, Yangjie Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1840 - 1846

Published: Feb. 8, 2024

Abstract Herein, we report a chemo‐ and regioselective Rh‐catalyzed redox C7‐spiroannulation reaction of N ‐benzo[ d ]imidazole indolines with maleimides, resulting in series indoline fused azaspirocycles up to 92% yield. The synthetic utility is demonstrated by the synthesis highly functionalized nitrogen‐containing spiropolycyclic skeletons. annulation could also be performed maleic esters acrylates. products were purified simple filtration. Rh catalyst can recycled, at gram‐scale using 0.5 mol% catalyst, which makes this protocol potentially applicable industry. Moreover, efficient post‐modification pharmaceutical molecules demonstrates its practicability.

Language: Английский

Citations

2
Base-Induced Decarboxylative 1,1-Alkoxy Thiolation via Hydrothiolation of Vinylene Carbonate DOI
Raju Mandal, Subhendu Ghosh, Tamanna Khandelia

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16655 - 16660

Published: Nov. 14, 2023

A base-mediated 1,1-difunctionalization of vinylene carbonate has been achieved using two different nucleophiles, namely, thiol and alcohol, with the assistance air (O2). In alcoholic solvents, decarboxylation occurs at room temperature to provide a 1,1-difunctionalized product, where serves as an ethynol (C2) synthon in this three-component reaction. On other hand, acetonitrile, exclusive hydrothiolation under basic conditions temperature. This method offers one-pot decarboxylative regioselective difunctionalization for construction α-alkoxy-β-hydroxy sulfide.

Language: Английский

Citations

4
Harnessing reductive BF2-complexation via Ru(II)-catalyzed N-O cleavage of isoxazoles DOI
Pritishree Panigrahi, Subhendu Ghosh, Tamanna Khandelia

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(68), P. 9109 - 9112

Published: Jan. 1, 2024

Developed here is a highly fluorescent organic N,O bidentate BF

Language: Английский

Citations

1
Solvent Dictated Organic Transformations DOI
Tamanna Khandelia, Pritishree Panigrahi, Subhendu Ghosh

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Solvent plays an important role in many chemical reactions. The C-H activation has been one of the most powerful tools organic synthesis. These reactions are often assisted by solvents which not only provide a medium for but also facilitate reaching to product stage. solvent helps reaction profile both chemically and energetically reach targeted product. Organic transformations via from assistance perspective discussed this review. Various such as tetrahydrofuran (THF), MeCN, dichloromethane (DCM), dimethoxyethane (DME), 1,2-dichloroethane (1,2-DCE), dimethylformamide (DMF), dimethylsulfoxide (DMSO), isopropyl nitrile (

Language: Английский

Citations

1