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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.7K
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...
4.7K
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
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.8K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
8.8K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.7K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

7.1K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
7.1K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.1K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.1K

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A simple and efficient method for constructing azepino[4,5-b]indole derivatives via acid catalysis.

Siva Senthil Kumar Boominathan1, Mutra Mohana Reddy1, Ruei-Jhih Hou1

  • 1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100 Shihquan Road, Kaohsiung 80708, Taiwan. jjwang@kmu.edu.tw.

Organic & Biomolecular Chemistry
|February 7, 2017
PubMed
Summary

A novel synthetic method creates important azepino[4,5-b]indole compounds using Brønsted acid catalysis. This efficient and green approach offers simple operations and high yields for valuable chemical synthesis.

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Area of Science:

  • Organic Synthesis
  • Medicinal Chemistry
  • Catalysis

Background:

  • Azepino[4,5-b]indole derivatives are crucial in medicinal chemistry.
  • Existing synthetic routes may lack efficiency or employ harsh conditions.

Purpose of the Study:

  • To develop a new, efficient synthetic methodology for azepino[4,5-b]indole derivatives.
  • To utilize Brønsted acid catalysis for this transformation.

Main Methods:

  • A novel synthetic protocol was established.
  • The reaction was catalyzed by a Brønsted acid.
  • Optimization of reaction parameters was performed.

Main Results:

  • The protocol successfully synthesized biologically important azepino[4,5-b]indole derivatives.
  • High reaction yields were achieved.
  • The reaction conditions were found to be mild and environmentally benign.

Conclusions:

  • A simple, efficient, and green synthetic method for azepino[4,5-b]indoles has been developed.
  • This methodology offers a valuable tool for accessing these important compounds.
  • The protocol's operational simplicity and high yields make it attractive for further applications.