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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.2K
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.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
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Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

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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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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...
3.8K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.4K
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...
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Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

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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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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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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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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Methods for Hydroxamic Acid Synthesis.

Mohammad A Alam1

  • 1Department of Chemistry and Physics, College of Science and Mathematics, Arkansas State University, Jonesboro, AR 72467, USA.

Current Organic Chemistry
|June 23, 2020
PubMed
Summary
This summary is machine-generated.

Substituted hydroxamic acids are versatile pharmacophores that chelate metal ions to modulate enzymes. This review details their synthesis and applications, covering reagents and novel molecule preparation.

Keywords:
Hydroxamic acidscatalytic reactioncoupling reactionsdirect synthesishydroxy laminemutagens

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis

Background:

  • Substituted hydroxamic acids are well-established pharmacophores.
  • They effectively chelate biologically significant metal ions.
  • These compounds modulate critical enzymes like HDACs, urease, metallopeptidase, and carbonic anhydrase.

Purpose of the Study:

  • To provide a comprehensive review of synthetic methodologies for hydroxamic acid derivatives.
  • To highlight the applications of these derivatives in synthesizing novel molecules.
  • To consolidate recent advancements in the field for researchers.

Main Methods:

  • Review of existing literature on hydroxamic acid synthesis and applications.
  • Compilation of various synthetic routes and strategies.
  • Description of preparation methods for hydroxylamine donating reagents.

Main Results:

  • Detailed overview of diverse synthetic approaches for hydroxamic acids.
  • Exploration of their utility in constructing novel chemical entities.
  • Inclusion of information on commercially available and prepared reagents.

Conclusions:

  • Hydroxamic acid derivatives offer significant potential in drug discovery and chemical synthesis.
  • This review serves as a primary resource for synthetic strategies and applications.
  • Further research into novel hydroxamic acid derivatives is warranted.