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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.3K
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...
4.3K
Preparation of Amides01:29

Preparation of Amides

3.7K
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...
3.7K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.0K
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...
3.0K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.1K
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...
4.1K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.8K
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...
3.8K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.5K
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.
3.5K

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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2-Azidoacrylamides as compact platforms for efficient modular synthesis.

Hinano Takemura1, Sayuri Goto, Takamitsu Hosoya

  • 1Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan. s-yoshida.cb@tmd.ac.jp.

Chemical Communications (Cambridge, England)
|November 26, 2020
PubMed
Summary

Researchers developed efficient methods for molecule assembly using triazole formations and Michael reactions. These techniques enable the iterative synthesis of complex tetrakis(triazole) structures from compact platform molecules.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Molecular assembly is crucial for creating complex chemical structures.
  • Efficient synthetic routes are needed for novel molecule development.

Purpose of the Study:

  • To disclose efficient methods for assembling modules using triazole formations and Michael reactions.
  • To demonstrate the utility of 2-triazolylacrylamides in Michael additions.

Main Methods:

  • Utilized orthogonal triazole formations and Michael reactions for module assembly.
  • Employed 2-triazolylacrylamides as electrophilic platforms for Michael additions.
  • Performed iterative synthesis to construct tetrakis(triazole) compounds.

Main Results:

  • Achieved efficient assembly of modules with compact platform molecules.
  • Demonstrated successful Michael additions with various nucleophiles.
  • Successfully accomplished iterative synthesis of a tetrakis(triazole) structure.

Conclusions:

  • Developed efficient and versatile methods for constructing complex molecules.
  • Highlighted the effectiveness of triazole formations and Michael reactions in synthesis.
  • The disclosed methods offer a pathway for creating novel tetrakis(triazole) derivatives.