Video Experimental Relacionado

Updated: Jun 23, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Acceso modular a los oxetanos funcionalizados como bioisósteros de benzoilo

Dayu Tian¹, Guang Chen¹, Xiaocheng Wang¹

¹Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.

Journal of the American Chemical Society

|June 21, 2024

Resumen

La síntesis de 3-arilo oxetanos funcionalizados, valiosos bioisósteros para el descubrimiento de fármacos, ahora es accesible. Una nueva estrategia modular que utiliza tricloroacetimidatos de oxetanilo supera los obstáculos sintéticos anteriores para el desarrollo de fármacos y productos agroquímicos.

Área de la Ciencia:

Química medicinal
Síntesis orgánica
Investigación agroquímica

Sus antecedentes:

El bioisosterismo es clave para optimizar las propiedades del fármaco.
Los 3-Aryloxetanos son importantes bioisósteros del benzoilo, pero también son sintéticamente difíciles.
Uso limitado en productos farmacéuticos y agroquímicos debido a dificultades sintéticas.

Objetivo del estudio:

Desarrollar una estrategia sintética modular para los 3-arilo-oxetanos funcionalizados.
Facilitar el acceso a los análogos de oxetano para el descubrimiento de fármacos y las aplicaciones agroquímicas.
Para superar los desafíos sintéticos asociados con los 3-arilo oxetanos.

Principales métodos:

Una nueva síntesis modular que utiliza tricloroacetimidatos de oxetanilo.
Estrategia inspirada en la glucosilación de Schmidt, utilizando haluros de arilo y nucleófilos.
Aplicación en la funcionalización de última etapa y en la síntesis analógica.

Principales resultados:

Desarrolló un protocolo operacionalmente simple para diversos oxetanos funcionalizados.
Se ha demostrado una amplia aplicabilidad a través de la funcionalización en etapa tardía de moléculas complejas.
Permitió la síntesis rápida de análogos de oxetano de compuestos bioactivos conocidos y medicamentos comercializados.

Conclusiones:

La nueva estrategia permite un fácil acceso a los valiosos 3-arilo-oxetanos.
Este enfoque facilita la exploración de los oxetanos en el descubrimiento de fármacos y agroquímicos.
Los conocimientos mecánicos sugieren que el oxígeno oxetano estabiliza los intermediarios clave de carbocatión.

Más Videos Relacionados

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Videos de Conceptos Relacionados

Reactions at the Benzylic Position: Oxidation and Reduction

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...