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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
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...
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Diazonium Group Substitution: –OH and –H01:19

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.8K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.4K
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...
3.4K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
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...
2.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
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.
3.2K

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Updated: Jun 21, 2025

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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N-Functionalization of 1,2-Azaborines.

Hyelee Lee1,2, Marisol Alvarado1, Sarah Ingram1,3

  • 1Department of Chemistry, Boston College, Chestnut Hill, MA 02467-3860, USA.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
|July 15, 2024
PubMed
Summary
This summary is machine-generated.

New methods enable the N-functionalization of 1,2-azaborines using various carbon electrophiles. This research synthesizes novel BN isosteres of trans-stilbene and lisdexamfetamine derivatives.

Keywords:
BN heterocyclesN-functionalizationaminationazaborinescross-coupling

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Materials Science

Background:

  • 1,2-Azaborines are heterocyclic compounds with unique electronic properties.
  • Functionalization of azaborine scaffolds is crucial for developing new molecules.
  • Existing methods for N-functionalization are limited.

Purpose of the Study:

  • To develop general protocols for the N-functionalization of 1,2-azaborines.
  • To synthesize novel BN isosteres of biologically relevant molecules.
  • To expand the synthetic utility of 1,2-azaborine chemistry.

Main Methods:

  • Reaction of 1,2-azaborines with C(sp³), C(sp²), and C(sp) electrophiles.
  • Utilizing developed methodology for targeted synthesis.
  • Characterization of synthesized compounds using spectroscopic techniques.

Main Results:

  • Established general protocols for N-functionalization of 1,2-azaborines.
  • Successfully synthesized a new BN isostere of trans-stilbene.
  • Synthesized a BN isostere of a lisdexamfetamine derivative using the developed methodology.

Conclusions:

  • The developed methodology provides a versatile route for N-functionalization of 1,2-azaborines.
  • This work expands the scope of azaborine chemistry and enables access to novel BN isosteres.
  • The synthesized compounds hold potential for applications in medicinal chemistry and materials science.