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α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

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Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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A New, Convenient Way to Fully Substituted α,β-Unsaturated γ-Hydroxy Butyrolactams.

Alexander V Aksenov1, Dmitrii A Aksenov1, Igor A Kurenkov1

  • 1Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia.

International Journal of Molecular Sciences
|June 28, 2023
PubMed
Summary

Researchers developed a new two-step method to synthesize functionalized 5-hydroxy 3-pyrrolin-2-ones. This efficient protocol yields diverse γ-hydroxy butyrolactams, valuable for synthetic organic and medicinal chemistry applications.

Keywords:
5-hydroxy-3-pyrrolin-2-onescascade transformationschalcones

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • 5-hydroxy 3-pyrrolin-2-ones are valuable scaffolds in medicinal chemistry.
  • Developing efficient synthetic routes to functionalized lactams is crucial.

Purpose of the Study:

  • To describe a novel two-step synthesis of highly functionalized 5-hydroxy 3-pyrrolin-2-ones.
  • To prepare diverse 3,5-di-aryl/heteroaryl-4-benzyl substituted α,β-unsaturated γ-hydroxy butyrolactams.

Main Methods:

  • Addition reaction of potassium cyanide (KCN) with chalcones.
  • Base-catalyzed ring condensation of β-cyano ketones with het(aryl)aldehydes.

Main Results:

  • Successful synthesis of novel, highly functionalized 5-hydroxy 3-pyrrolin-2-ones.
  • Preparation of various 3,5-di-aryl/heteroaryl-4-benzyl substituted γ-hydroxy butyrolactams.
  • The protocol offers a versatile route to complex lactam structures.

Conclusions:

  • A facile and efficient two-step protocol for synthesizing functionalized γ-hydroxy butyrolactams has been established.
  • The synthesized compounds hold potential for applications in synthetic organic and medicinal chemistry.