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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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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).
2.3K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.6K
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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Cycloaddition Reactions: Overview01:16

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2.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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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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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Pd-Catalyzed One-Pot Synthesis of Indole-3-carboxylic Acids via a Sequential Water-Mediated Nucleophilic Addition to

Tengfei Zhang1, Kai Hong1, Ye Wu1

  • 1College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin 150040, P. R. China.

The Journal of Organic Chemistry
|August 28, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a novel palladium-catalyzed reaction using trace water to synthesize 4-amino/alkoxyindole-3-carboxylic acids from readily available precursors. This efficient one-pot method combines multiple steps for rapid indole derivative assembly.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Indole-3-carboxylic acids are crucial scaffolds in pharmaceuticals.
  • Efficient synthesis of multisubstituted indoles remains a challenge.
  • Palladium-catalyzed cross-coupling reactions are vital in organic synthesis.

Purpose of the Study:

  • To develop a novel, efficient, and versatile one-pot synthetic strategy for 4-amino/alkoxyindole-3-carboxylic acid derivatives.
  • To integrate nucleophilic substitution and palladium-catalyzed cross-coupling into a single reaction system.
  • To demonstrate broad functional group compatibility and good yields.

Main Methods:

  • Utilizing 4-bromoindole-3-carboxylic acid amides or esters as substrates.
  • Employing a palladium catalyst (PdCl2), Xantphos ligand, and cesium pivalate additive.
  • Leveraging trace water as a promoter in a one-pot reaction system.

Main Results:

  • Successful synthesis of 4-amino/alkoxyindole-3-carboxylic acid products.
  • Demonstration of efficient synergy between nucleophilic substitution and Pd-catalyzed C-N/C-O cross-coupling.
  • Achieved modular and rapid assembly of multisubstituted indole-3-carboxylic acids with broad functional group tolerance.
  • Maintained good reaction yields throughout the process.

Conclusions:

  • The developed trace water-promoted, palladium-catalyzed one-pot reaction offers an efficient and versatile route to substituted indole-3-carboxylic acids.
  • This method simplifies multistep transformations, facilitating rapid synthesis of valuable indole derivatives.
  • The approach shows significant potential for drug discovery and development due to its broad applicability and efficiency.