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Related Concept Videos

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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Acid Halides to Esters: Alcoholysis01:12

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Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Styrylpyrazoles: Properties, Synthesis and Transformations.

Pedro M O Gomes1, Pedro M S Ouro1, Artur M S Silva1

  • 1LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.

Molecules (Basel, Switzerland)
|December 16, 2020
PubMed
Summary
This summary is machine-generated.

This review explores styrylpyrazoles, highlighting their medicinal chemistry potential. These compounds, featuring a styryl group on the pyrazole core, show promising biological activities and synthesis methods.

Keywords:
biological activityorganic synthesispyrazolesreactivitystyrylpyrazoles

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Heterocyclic Chemistry

Background:

  • Pyrazole derivatives are recognized as privileged scaffolds in medicinal chemistry.
  • Numerous pyrazole derivatives have been synthesized and investigated for diverse biological activities.
  • Styrylpyrazoles, a specific class, have received limited research attention despite early synthesis reports.

Purpose of the Study:

  • To provide a comprehensive overview of styrylpyrazoles.
  • To summarize the synthesis, properties, and biological activities of styrylpyrazoles.
  • To underscore the potential applications of styrylpyrazoles in medicinal chemistry.

Main Methods:

  • Literature review of scientific publications on styrylpyrazoles.
  • Analysis of synthetic routes for incorporating styryl groups onto the pyrazole backbone.
  • Compilation of data on biological activities and chemical transformations.

Main Results:

  • Styrylpyrazoles can be synthesized through various established organic chemistry methods.
  • These compounds exhibit a range of biological activities, indicating therapeutic potential.
  • The styryl moiety can be introduced at different positions of the pyrazole ring, influencing properties.

Conclusions:

  • Styrylpyrazoles represent an underexplored class of compounds with significant medicinal chemistry relevance.
  • Further research into styrylpyrazoles is warranted to fully realize their therapeutic and synthetic potential.
  • This review serves as a foundational resource for future investigations into styrylpyrazole chemistry.