Related Experiment Video
Updated: Sep 30, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis and Properties of 1-Azapyrenes
Arpine Vardanyan1, Sebastian Boldt1, Alexander Villinger1
1Institut für Chemie, Universität Rostock, A.-Einstein-Street 3a, 18059 Rostock, Germany.
Abstract:
A straightforward method for the synthesis of a series of hitherto unknown 1-azapyrenes is reported, which relies on a combination of Pd-catalyzed cross-coupling reactions with Brønsted acid-mediated cycloisomerization reactions. The methodology is highly modular and allows an efficient synthesis of various substituted products in high yields. The structural, electrochemical, and photophysical properties of 1-azapyrenes have been studied by ultraviolet-visible (UV-vis) and fluorescence spectroscopies, cyclic voltammetry, and density functional theory (DFT) calculations.
More Related Videos
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
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...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

