Calder, E. D.D., Sharif, S. A.I., McGonagle, F. I. and Sutherland, A. (2015) One-pot synthesis of 5-amino-2,5-dihydro-1-benzoxepines: access to pharmacologically active heterocyclic scaffolds. Journal of Organic Chemistry, 80(9), pp. 4683-4696. (doi: 10.1021/acs.joc.5b00583) (PMID:25847814)
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Abstract
A one-pot multibond-forming process involving a thermally mediated Overman rearrangement and a ring closing metathesis reaction of allylic trichloroacetimidates bearing a 2-allyloxyaryl group has been developed for the synthesis of 5-amino-substituted 2,5-dihydro-1-benzoxepines. Chemoselective reduction and functionalization of these compounds allowed access to a range of pharmacologically active 5-amino-2,3,4,5-tetrahydro-1-benzoxepine scaffolds.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Sutherland, Professor Andrew |
| Authors: | Calder, E. D.D., Sharif, S. A.I., McGonagle, F. I., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Copyright Holders: | Copyright © 2015 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 80(9):4683-4696 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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