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Related Concept Videos

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.8K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.8K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.6K
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...
3.6K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.5K
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...
4.5K
Preparation of Amides01:29

Preparation of Amides

4.2K
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...
4.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

4.2K
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...
4.2K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.8K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
4.8K

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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A novel method for heterocyclic amide-thioamide transformations.

Walid Fathalla1, Ibrahim A I Ali2, Pavel Pazdera3

  • 1Physics and Math. Engineering Dept., Faculty of Engineering, Port-Said University, Port Said, Egypt.

Beilstein Journal of Organic Chemistry
|February 24, 2017
PubMed
Summary
This summary is machine-generated.

This study presents a new two-step method to convert heterocyclic amides into valuable heterocyclic thioamides. The convenient process achieves excellent yields for synthesizing these important chemical compounds.

Keywords:
N-cyclohexyl dithiocarbamate cyclohexylammonium saltheterocyclic amidesheterocyclic thioamidesnovel thiating agentthiation

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry

Background:

  • Heterocyclic amides are important precursors in organic synthesis.
  • Efficient methods for synthesizing heterocyclic thioamides are crucial for various applications.

Purpose of the Study:

  • To develop a novel and convenient method for the transformation of heterocyclic amides into heterocyclic thioamides.
  • To achieve high yields in the synthesis of heterocyclic thioamides.

Main Methods:

  • A two-step synthetic approach was employed.
  • Step 1: Chlorination of heterocyclic amides to yield chloroheterocycles.
  • Step 2: Reaction of chloroheterocycles with N-cyclohexyl dithiocarbamate cyclohexylammonium salt in chloroform at 61 °C for 12 hours.

Main Results:

  • The method successfully transformed heterocyclic amides into heterocyclic thioamides.
  • Excellent yields were obtained for the target heterocyclic thioamides.
  • The process is described as novel and convenient.

Conclusions:

  • The developed two-step method offers an efficient route for synthesizing heterocyclic thioamides from heterocyclic amides.
  • This transformation provides a valuable tool for organic chemists.
  • The method's convenience and high yields make it attractive for practical applications.