Isoxazole derivatives as anticancer agent: A review on synthetic strategies, mechanism of action and SAR studies

European Journal of Medicinal Chemistry, Journal Year: 2021, Volume and Issue: 221, P. 113511 - 113511

Published: May 6, 2021

Language: Английский

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tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Chemistry - An Asian Journal, Journal Year: 2019, Volume and Issue: 14(24), P. 4454 - 4492

Published: Sept. 20, 2019

The upsurge interest in the development of efficient methodologies for construction nitrogen-containing frameworks via use expedient reagents have been creating a renaissance contemporary organic chemistry. In this perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its unique structural features, it shows differential reactivity under different reaction conditions. These diverse reactivities resulted array complex N-containing molecules. primary objective present review bring latest findings TBN terms applications reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into limelight. For simplicity brevity, each section are explained with mechanism formation selected examples given.

Language: Английский

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A review of recent synthetic strategies and biological activities of isoxazole

Journal of Heterocyclic Chemistry, Journal Year: 2022, Volume and Issue: 60(4), P. 537 - 565

Published: Oct. 13, 2022

Abstract Among different heterocyclic compounds, isoxazole and their analogues are very important classes of compounds as they display an extensive range biological actions. This makes such scaffolds structures in the field medicinal chemistry. From literature assessment, is clinically proven to be effective anti‐bacterial, anti‐fungal, anti‐inflammatory, anti‐cancer, anti‐tubercular, anti‐neoplastic agent. The derivatives which exhibits adjustment structure have shown a high degree variety properties evident them beneficial progress novel bioactive drugs show enhanced effectiveness along with minor harmfulness. Structural aspects having aromaticity weaker nitrogen‐oxygen bonding provide potential site for ring cleavage. Thus, this system allows easier modifications substituents consequently make useful intermediates various synthetic routes compounds. Hence, synthesis evaluation isoxazole‐containing molecules wider therapeutic consequences always topic interest chemists. light comprehensive research on isoxazole, it thought worthwhile review pathways broad spectrum

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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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

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Iridium-catalyzed B–H insertion of sulfoxonium ylides and borane adducts: a versatile platform to α-boryl carbonyls

Chemical Communications, Journal Year: 2019, Volume and Issue: 56(3), P. 423 - 426

Published: Dec. 4, 2019

Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields most cases (51 examples; up 84%). This practical scalable reaction showed broad substrate scope, high functional-group compatibility could be applied late-stage modification structurally complex drug compounds. Further synthetic applications were also demonstrated.

Language: Английский

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Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4286 - 4291

Published: June 2, 2023

Two categories of tetrasubstituted phenols were prepared via the cycloaddition reaction vinyl sulfoxonnium ylides with cyclopropenones in a switchable manner. Copper carbenoid was proposed as active intermediate process 2,3,4,5-tetrasubstituted formation, while 2,3,5,6-tetrasubstituted generated direct [3 + 3] annulation under metal-free conditions. Further synthetic applications also demonstrated.

Language: Английский

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Metal-free cascade O–H double insertion between I^(III)/S^(VI)-ylides, carboxylic acids, and alcohols: modular access to unsymmetrical α,α-O,O-substituted ketones

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3234 - 3241

Published: Jan. 1, 2024

Herein, we present a cascade O–H double insertion reaction between I (III) /S (VI) -ylides, carboxylic acids, and alcohols under metal-free conditions, enabling the modular synthesis of unsymmetrical α,α- O , -substituted ketones.

Language: Английский

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A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5811 - 5816

Published: June 28, 2024

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization hybrid I(III)/S(VI) is presented. This process allows efficient P–H insertion under Cu catalysis, enabling synthesis ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC(S)OR, KSCN mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, thiocyanation accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, various product derivatizations highlight synthetic utility this protocol.

Language: Английский

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Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives

Organic Letters, Journal Year: 2020, Volume and Issue: 22(16), P. 6600 - 6604

Published: Aug. 10, 2020

A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, β-keto thiosulfones, respectively. The nucleophilic addition two molecular to construct sulfone-substituted 1,4-dione compounds the highlight this work.

Language: Английский

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