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Related Concept Videos

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 Halides to Carboxylic Acids: Hydrolysis01:01

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Carboxylic Acids to Acid Chlorides01:18

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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Preparation of 1° Amines: Gabriel Synthesis01:28

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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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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α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

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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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Exploring Phthalimide as the Acid Component in the Passerini Reaction.

Jingyao Li1, Qiang Zheng1, Alexander Dömling1,2

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Organic Letters
|January 16, 2024
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Summary

Phthalimide derivatives can now participate in the Passerini reaction, expanding synthetic chemistry. This discovery enables the creation of novel molecular scaffolds and diverse compound libraries using stable building blocks.

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Area of Science:

  • Organic chemistry
  • Synthetic chemistry
  • Medicinal chemistry

Background:

  • Multicomponent reactions (MCRs), like the Passerini reaction, are vital for synthesizing drug-like molecules and compound libraries.
  • A key limitation of the Passerini reaction is the restricted range of available carboxylic acid components, hindering structural diversity.

Purpose of the Study:

  • To overcome the structural constraints of the Passerini reaction by identifying novel acid components.
  • To explore the utility of phthalimide derivatives as alternative acid components in the Passerini reaction.
  • To synthesize diverse and complex molecules using this expanded reaction scope.

Main Methods:

  • Investigated the reactivity of phthalimide and its derivatives in the Passerini multicomponent reaction.
  • Evaluated the stability and synthetic utility of phthalimide-based products.
  • Characterized the synthesized molecules to confirm structural diversity and complexity.

Main Results:

  • Phthalimide and its derivatives successfully function as carboxylic acid surrogates in the Passerini reaction.
  • The phthalimide moiety offers advantages such as oxidative stability, thermal resistance, and solvent inertness.
  • This method allows for the synthesis of a wide array of intricate molecular structures.

Conclusions:

  • Phthalimide derivatives represent a significant advancement as NH-based acid components in Passerini multicomponent reactions.
  • This approach broadens the scope of MCRs and facilitates the development of novel molecular scaffolds.
  • The findings address the need for innovative synthetic strategies in drug discovery and chemical biology.