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Preparation of Amides01:29

Preparation of Amides

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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...
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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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...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.9K
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...
4.9K
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

4.3K
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...
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.7K
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...
3.7K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

4.3K
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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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Macrocycle Synthesis by Chloride-Templated Amide Bond Formation.

Vicente Martí-Centelles1, M Isabel Burguete1, Santiago V Luis1

  • 1Departamento de Química Inorgánica y Orgánica, Universitat Jaume I , Avenida de Vicent Sos Baynat s/n, 12071 Castellón, Spain.

The Journal of Organic Chemistry
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Researchers developed new pseudopeptidic macrocyclic compounds using anion-templated amide bond formation. Chloride ions significantly improved macrocyclization yields by kinetically favoring the folded conformation of the precursor molecule.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Macrocyclic compounds are important in various fields, including medicine and materials science.
  • Efficient synthesis of macrocycles remains a challenge, particularly for pseudopeptidic structures.

Purpose of the Study:

  • To develop a novel method for synthesizing pseudopeptidic macrocyclic compounds.
  • To investigate the role of anion templating in the macrocyclization step.

Main Methods:

  • Preparation of pseudopeptidic macrocyclic compounds.
  • Employing an anion-templated amide bond formation reaction during macrocyclization.
  • Comparing yields of templated versus non-templated reactions.

Main Results:

  • A new family of pseudopeptidic macrocycles was successfully synthesized.
  • Chloride anion was identified as the most effective template, significantly improving macrocyclization yields.
  • The chloride template demonstrated a kinetic effect, promoting the correct precursor conformation and lowering the activation energy for macrocyclization.

Conclusions:

  • Anion-templated amide bond formation is an effective strategy for synthesizing pseudopeptidic macrocycles.
  • Chloride templating offers a significant yield improvement over non-templated reactions.
  • The mechanism involves a kinetic advantage conferred by the template, facilitating the cyclization process.