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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems01:15

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Oxidative reactions are pivotal in metabolizing numerous compounds, including pharmaceutical drugs. These reactions often occur in carbon-heteroatom systems, such as carbon-nitrogen, carbon-sulfur, and carbon-oxygen.
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
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Oxidation-Reduction Reactions03:11

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Reactions at the Benzylic Position: Oxidation and Reduction00:59

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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.
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Oxymercuration-Reduction of Alkenes02:36

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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.
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Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems01:19

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Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
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Multicomponent Reactions (MCRs) with o-Quinone Methides.

Maria Tereza M Martins1, Flaviana Rodrigues F Dias1, Raphael Silva M de Moraes1

  • 1Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, Programa de Pós-Graduação em Química, 24020-141, Niterói, Rio de Janeiro, Brazil.

Chemical Record (New York, N.Y.)
|February 3, 2022
PubMed
Summary
This summary is machine-generated.

This review details multicomponent reactions (MCRs) involving ortho-quinone methide (o-QM) intermediates. These reactive species are crucial in organic synthesis, natural product construction, and biological applications.

Keywords:
biological compoundsgreen chemistrymulticomponent reactionone-pot reactionortho-quinone methide

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Ortho-quinone methides (o-QMs) are highly reactive intermediates.
  • Their generation and reactivity are key to various synthetic transformations.
  • Applications span organic synthesis to biological processes.

Purpose of the Study:

  • To provide a comprehensive overview of multicomponent reactions (MCRs) utilizing o-QM intermediates.
  • To highlight the generation methods and versatile reactivity of o-QMs.
  • To showcase applications in synthesis and biological contexts.

Main Methods:

  • Review of literature on o-QM generation and reactions.
  • Discussion of MCRs proceeding via o-QM intermediates.
  • Examples of synthetic and biological applications.

Main Results:

  • o-QMs can be generated via eliminative processes or photochemistry.
  • They participate in nucleophilic attacks and inverse-electron demand Diels-Alder reactions.
  • Applications include cascade reactions for natural product synthesis and prodrug cleavage.

Conclusions:

  • o-QM intermediates offer versatile reactivity for complex molecule construction.
  • Their role in MCRs is significant for both synthetic and biological chemistry.
  • Further exploration of o-QM chemistry promises novel applications.