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Related Concept Videos

Nitriles to Carboxylic Acids: Hydrolysis01:08

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Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
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Preparation of 1° Amines: Azide Synthesis01:22

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
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Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
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Acid Halides to Amides: Aminolysis01:07

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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.
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Radical Azidation/Cyclization Cascade of N-Acrylohydrazides: Access to Biologically Relevant Azido-Pyrazolones.

Chandra Shekhar Nishad1, Biplab Banerjee1

  • 1Department of Chemistry, Central University of Punjab, Bathinda 151401, India.

The Journal of Organic Chemistry
|March 23, 2026
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A novel, metal-free method synthesizes valuable azido-pyrazolones using sustainable radical azidation and cyclization. This environmentally friendly approach offers broad applicability and practical utility for drug discovery.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Sustainable Chemistry

Background:

  • Azido-pyrazolones are crucial scaffolds in medicinal chemistry.
  • Existing synthetic methods often involve toxic reagents or harsh conditions.
  • Development of sustainable and efficient synthetic routes is highly desirable.

Purpose of the Study:

  • To develop a metal-free, sustainable method for synthesizing azido-pyrazolones.
  • To explore a radical azidation/cyclization cascade reaction for constructing these heterocycles.
  • To demonstrate the practicality and broad applicability of the developed method.

Main Methods:

  • Utilized a radical azidation/5-enderig cyclization cascade reaction.
  • Employed N-acrylohydrazides as starting materials.
  • Used a hypervalent iodine(III) reagent and trimethylsilyl azide.

Main Results:

  • Achieved synthesis of pharmaceutically important azido-pyrazolones.
  • Demonstrated a broad substrate scope with good to excellent product yields.
  • Successfully performed gram-scale synthesis and further functionalization, including drug molecule conjugation.

Conclusions:

  • The developed method is metal-free, sustainable, and operationally simple.
  • It offers an attractive, environmentally friendly route to azido-pyrazolones.
  • The method shows significant potential for applications in drug discovery and development.