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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...
3.9K
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
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
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

8.8K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
8.8K
Preparation of Amides01:29

Preparation of Amides

3.0K
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...
3.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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

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Updated: Jun 27, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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1,2,3-Triazole-Containing Azamacrocycles from Chiral Triazolopeptoids: Synthesis and Solid-State Studies.

Alicja M Araszczuk1, Giovanni Pierri1, Rosaria Schettini1

  • 1Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 3, 2024
PubMed
Summary

Two novel chiral macrocyclic compounds containing 1,2,3-triazole were synthesized and characterized. These triazolopeptoids and their reduced azamacrocycle derivatives exhibit unique conformational properties and form stable borane complexes, highlighting the utility of triazole-containing macrorings.

Keywords:
Azamacrocyclesborane complexespeptidomimeticspeptoidstriazoles

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Medicinal Chemistry

Background:

  • Macrocyclic compounds are crucial in various chemical and biological applications.
  • 1,2,3-triazole moieties offer unique electronic and structural properties.
  • Chiral macrocycles are valuable for asymmetric synthesis and molecular recognition.

Purpose of the Study:

  • To synthesize novel chiral 1,2,3-triazole-containing macrocyclic oligoamides.
  • To investigate the conformational behavior of these macrocycles using theoretical and spectroscopic methods.
  • To explore the reduction of amide groups to form novel azamacrocycles and their properties.

Main Methods:

  • Solid-phase synthesis of linear precursors.
  • High-dilution macrocyclization reactions.
  • Density Functional Theory (DFT) calculations and Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Borane reduction of amide groups.
  • X-ray diffraction studies.

Main Results:

  • Successful synthesis of two new chiral 1,2,3-triazole-containing macrocyclic oligoamides (triazolopeptoids 4 and 5).
  • DFT and NMR studies elucidated the complex conformational interplay of Nα-chiral side chains.
  • Novel azamacrocycles (6-9) were obtained via BH3-mediated reduction.
  • Borane complexes of azamacrocycles 6 and 9 (10 and 11) were detected and characterized by X-ray diffraction, confirming unique properties.

Conclusions:

  • The study successfully synthesized and characterized novel chiral triazole-containing macrocycles and their azamacrocycle derivatives.
  • The conformational analysis revealed intricate structure-property relationships.
  • The formation of stable borane complexes underscores the unique characteristics of these 1,2,3-triazole-containing macrorings for potential applications.