Synthesis of structurally diverse benzotriazoles via rapid diazotization and intramolecular cyclization of 1,2-aryldiamines

Faggyas, R. J., Sloan, N. L., Buijs, N. and Sutherland, A. (2019) Synthesis of structurally diverse benzotriazoles via rapid diazotization and intramolecular cyclization of 1,2-aryldiamines. European Journal of Organic Chemistry, 2019(31-32), pp. 5344-5353. (doi: 10.1002/ejoc.201900463)

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Abstract

An operationally simple method has been developed for the preparation of N‐unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2‐aryldiamines under mild conditions, using a polymer‐supported nitrite reagent and p‐tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N‐alkyl, ‐aryl, and ‐acyl ortho‐aminoanilines leading to the synthesis of N1‐substituted benzotriazoles. The synthetic utility of this one‐pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α‐amino acid analogue.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Sloan, Miss Nikki and Sutherland, Professor Andrew and Faggyas, Réka
Authors: Faggyas, R. J., Sloan, N. L., Buijs, N., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:European Journal of Organic Chemistry
Publisher:Wiley
ISSN:1434-193X
ISSN (Online):1099-0690
Published Online:16 April 2019
Copyright Holders:Copyright © 2019 The Authors
First Published:First published in European Journal of Organic Chemistry 2019(31-32):5344–5353
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
3048960EPSRC-IAA: Early Stage Commercialisation of a PET Imaging Agent for the Detection of Cardiovascular Disease and CancerAndrew SutherlandEngineering and Physical Sciences Research Council (EPSRC)EP/R511705/1Chemistry