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Preparation of Amides01:29

Preparation of Amides

3.9K
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...
3.9K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.5K
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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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.8K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.8K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.8K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.8K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.5K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
4.5K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

4.0K
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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One-Pot Method to Access 1,3,4-Oxadiazol-2(3H)-ones Using Carbonyldiimidazole.

Rajib Islam1,2, Colin D McMillen1, Kaleb R Marahrens1

  • 1Department of Chemistry, Clemson University, Clemson, South Carolina 29634, United States.

The Journal of Organic Chemistry
|December 31, 2025
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A new metal-free, one-pot synthesis efficiently produces 1,3,4-oxadiazol-2(3H)-ones from simple starting materials. This simplified method offers moderate to excellent yields for these valuable heterocyclic compounds.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Heterocyclic Chemistry

Background:

  • 1,3,4-oxadiazol-2(3H)-ones are important heterocyclic scaffolds with diverse biological activities.
  • Existing synthetic routes to these compounds often involve multiple steps, harsh conditions, or expensive reagents.

Purpose of the Study:

  • To develop a convenient, metal-free, one-pot synthetic method for 1,3,4-oxadiazol-2(3H)-ones.
  • To establish a simplified and scalable approach using readily available starting materials.

Main Methods:

  • The synthesis utilizes hydrazines, carboxylic acids, and 1,1'-carbonyldiimidazole (CDI) as an activating agent.
  • Triethylamine (TEA) is employed as a base in a one-pot reaction.
  • The reaction conditions were optimized for yield and purity.

Main Results:

  • The developed method successfully synthesized various 1,3,4-oxadiazol-2(3H)-ones.
  • Moderate to excellent yields were achieved for the target heterocycles.
  • Substrate scope investigation confirmed broad applicability and scalability of the protocol.

Conclusions:

  • A facile and efficient metal-free one-pot synthesis for 1,3,4-oxadiazol-2(3H)-ones has been established.
  • This method provides a significant improvement over existing synthetic strategies.
  • The protocol is suitable for accessing diverse analogs and for larger-scale preparations.