Henry, M. C., Abbinante, V. M. and Sutherland, A. (2020) Iron-catalyzed regioselective synthesis of 2-arylbenzoxazoles and 2-arylbenzothiazoles via alternative reaction pathways. European Journal of Organic Chemistry, 2020(19), pp. 2819-2826. (doi: 10.1002/ejoc.202000014)
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Abstract
A one‐pot regioselective method for the preparation of 2‐arylbenzoxazoles from N‐arylbenzamides has been developed using iron(III)‐catalyzed bromination of the aryl ring, followed by copper(I)‐catalyzed O‐cyclization with the benzamide side chain. In contrast, reaction of N‐arylthiobenzamides with N‐bromosuccinimide and iron triflimide led directly to the isolation of the corresponding 2‐arylbenzothiazoles via intramolecular C–S bond formation. Mechanistic and control experiments suggest that in this case, bromination occurs at the sulfur atom, resulting in a reactive intermediate that can undergo electrophilic aromatic substitution and S‐cyclization. The scope of both processes was explored yielding a range of structural analogues, including a pharmaceutically active compound for the treatment of Duchenne muscular dystrophy and an affinity agent of the amyloid‐beta protein in Alzheimer's disease.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Henry, Mr Martyn and Abbinante, Vincenzo Mirco and Sutherland, Professor Andrew |
| Authors: | Henry, M. C., Abbinante, V. M., 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: | 27 February 2020 |
| Copyright Holders: | Copyright © 2020 The Authors |
| First Published: | First published in European Journal of Organic Chemistry 2020(19): 2819-2826 |
| Publisher Policy: | Reproduced under a Creative Commons licence |
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