Related Experiment Video
Updated: Apr 30, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Photochemical C4-Selective C-H Amination of Quinolines via N-Shift of Heteroaryl Azides
Alessandro Dimasi1, Arianna Montoli1, Giovanni Macetti1
1Department of Chemistry, Università degli Studi di Milano, Via Camillo Golgi 19, 20133, Milano, Italy.
Abstract:
Access to 3,4-diaminoazines is limited by regioselectivity challenges in azine functionalization. We report a photochemical strategy enabling the direct synthesis of 3,4-diaminoazines through C3-to-C4 nitrogen migration (N-shift). Blue LED irradiation of 3-azidoquinolines at room temperature allows C4-selective C-H amination while concurrently installing diverse amines at the C3-position. In contrast, N-shifts in 3-azidopyridines preferentially form diazepines, reflecting divergent reactivity governed by N-heterocycle electronics, as supported by computational analysis.
More Related Videos
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...