Related Experiment Video
Updated: Feb 1, 2026

Bioorthogonal Chemical Imaging of Cell Metabolism Regulated by Aromatic Amino Acids
Published on: May 12, 2023
Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids
Mostafa M Amer1, Ana C Carrasco2, Daniel J Leonard1
1School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.
Abstract:
Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C═O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.
Related Concept Videos
Amino acids
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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...
Electrophilic Aromatic Substitution: Overview
Amino Acid Catabolism

