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Preparation of Amides01:29

Preparation of Amides

4.0K
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...
4.0K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.4K
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...
4.4K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.5K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.3K
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...
4.3K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.3K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
6.3K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.0K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.0K

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Amidation Strategy for Final-Step α-Hydroxytropolone Diversification.

Alex J Berkowitz1,2, Rudolf G Abdelmessih1, Ryan P Murelli1,2

  • 1Department of Chemistry, Brooklyn College, The City University of New York, 2900 Bedford Avenue, Brooklyn, NY, 11210, United States.

Tetrahedron Letters
|March 16, 2019
PubMed
Summary
This summary is machine-generated.

This study introduces a scalable method to create diverse alpha-hydroxytropolones (αHTs), which are key fragments for developing enzyme inhibitors used in chemical biology and medicinal chemistry.

Keywords:
AmidationChemical Probe SynthesisMetal-Binding FragmentOxidopyrylium CycloadditionTropolones

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Area of Science:

  • Medicinal Chemistry
  • Chemical Biology
  • Organic Synthesis

Background:

  • Alpha-hydroxytropolones (αHTs) are recognized as effective fragments for inhibiting metalloenzymes.
  • They serve as a foundation for designing potent inhibitors targeting therapeutically significant enzymes.

Purpose of the Study:

  • To develop a versatile final-step amidation strategy for diversifying αHT structures.
  • To enable the synthesis of novel αHT derivatives for chemical biology and medicinal chemistry applications.

Main Methods:

  • A scalable and chromatography-free synthesis of a carboxylic acid-appended αHT precursor was employed.
  • A final-step amidation approach was utilized for diversification.

Main Results:

  • Eight distinct amide-containing αHT compounds were successfully synthesized.
  • Three of these novel compounds are proposed for use as chemical probes.

Conclusions:

  • The described amidation strategy offers a robust method for αHT diversification.
  • This approach is expected to be widely adopted in chemical biology and medicinal chemistry research involving αHTs.