Late stage iodination of biologically active agents using a one-pot process from aryl amines

Sloan, N. L., Luthra, S. K., McRobbie, G., Pimlott, S. L. and Sutherland, A. (2017) Late stage iodination of biologically active agents using a one-pot process from aryl amines. RSC Advances, 7(86), pp. 54881-54891. (doi: 10.1039/C7RA11860K)

Abstract

A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(II) dichloride reduction and the use of the one-pot diazotisation–iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-D-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Pimlott, Dr Sally and Sloan, Dr Nikki and Sutherland, Professor Andrew
• Authors: Sloan, N. L., Luthra, S. K., McRobbie, G., Pimlott, S. L., and Sutherland, A.
• College/School: College of Medical Veterinary and Life Sciences > School of Medicine, Dentistry & Nursing
• Journal Name: RSC Advances
• Publisher: Royal Society of Chemistry
• ISSN: 2046-2069
• ISSN (Online): 2046-2069
• Published Online: 01 December 2017
• Copyright Holders: Copyright © 2017 The Authors
• First Published: First published in RSC Advances 7(86):54881-54891
• Publisher Policy: Reproduced under a Creative Commons License