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Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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 acid...
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

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:
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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Related Experiment Video

Updated: Jul 5, 2026

Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
13:42

Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets

Published on: November 2, 2011

A facile solid phase synthesis of tetramic acid.

Zhanxiang Liu1, Xiuxiu Ruan, Xian Huang

  • 1Department of Chemistry, Zhejiang University, Campus Xixi, Hangzhou, 310028, People's Republic of China.

Bioorganic & Medicinal Chemistry Letters
|July 11, 2003
PubMed
Summary

Researchers developed a method to synthesize N-protected tetramic acid derivatives. This process involves condensing N-acylated amino acids with a polymer-supported cyclic malonic acid ester, yielding high-purity compounds efficiently.

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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

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Last Updated: Jul 5, 2026

Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
13:42

Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets

Published on: November 2, 2011

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
12:06

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Medicinal Chemistry

Background:

  • Tetramic acid derivatives are important scaffolds in medicinal chemistry.
  • Efficient synthesis of these compounds is crucial for drug discovery.
  • Existing synthetic methods may have limitations in yield or purity.

Purpose of the Study:

  • To develop an efficient and high-yielding method for synthesizing N-protected tetramic acid derivatives.
  • To utilize polymer-supported reagents for improved synthesis and purification.
  • To explore the condensation of N-acylated amino acids with cyclic malonic acid esters.

Main Methods:

  • Condensation reaction between N-acylated amino acids and polymer-supported cyclic malonic acid ester.
  • Use of N,N'-Dicyclohexylcarbodiimide (DCC) and 4-Dimethylaminopyridine (DMAP) as coupling agents.
  • Cyclization of the intermediate resin by heating in an organic solvent.

Main Results:

  • Successful synthesis of N-protected tetramic acid derivatives.
  • Achieved good yields and high purity of the target compounds.
  • Demonstrated the utility of polymer-supported reagents in this synthesis.

Conclusions:

  • The described method provides an effective route to N-protected tetramic acid derivatives.
  • Polymer-supported synthesis offers advantages in terms of yield and purity.
  • This approach facilitates access to valuable chemical scaffolds for further research.