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 |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Sloan, Dr 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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