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Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies
Dissertation (MSc)--University of Pretoria, 2024.
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| Format: | Thesis |
| Language: | English |
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University of Pretoria
2024
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| _version_ | 1867613469392502784 |
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| access_status_str | Open Access |
| author2 | Riley, Darren Lyall |
| author_browse | Riley, Darren Lyall |
| author_facet | Riley, Darren Lyall |
| collection | Thesis |
| dc_rights_str_mv | © 2023 University of Pretoria. All rights reserved. The copyright in this work vests in the University of Pretoria. No part of this work may be reproduced or transmitted in any form or by any means, without the prior written permission of the University of Pretoria. |
| description | Dissertation (MSc)--University of Pretoria, 2024. |
| format | Thesis |
| id | oai:repository.up.ac.za:2263/95224 |
| institution | University of Pretoria (South Africa) |
| language | English |
| last_indexed | 2026-06-10T12:36:38.728Z |
| license_str | Other — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UPSpace — University of Pretoria Institutional Repository |
| publishDate | 2024 |
| publishDateRange | 2024 |
| publishDateSort | 2024 |
| publisher | University of Pretoria |
| publisherStr | University of Pretoria |
| record_format | dspace |
| source_str | UPSpace — University of Pretoria Institutional Repository |
| spelling | oai:repository.up.ac.za:2263/95224 Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies Riley, Darren Lyall bernicecurrie@gmail.com Panayides, Jenny-Lee Currie, Bernice Mercia UCTD Flow chemistry, Claisen rearrangement, Ring closing metathesis, 8-membered ring, benzo-fused heterocycle Dissertation (MSc)--University of Pretoria, 2024. Flow chemistry has become an appealing alternative synthetic technology globally over the last few decades finding application in both academic and industrial laboratories driven largely by the fact that it commonly provides higher selectivity, yield and purity compared to batch chemistry that has become time-consuming, ineffective, and challenging to scale up. This dissertation describes the application and development of a flow process towards the synthesis of an 8-membered oxygen-containing benzo-fused heterocycle. The synthesis consisted of six stages that included two allylation steps, a Claisen rearrangement, an alcohol protection, an aldehyde reduction and a ring-closing metathesis step. The target molecule, (Z)-7-isopropoxy-8-methoxy-3,6-dihydro-1H-benzo[c]oxocine 25, was selected with an interest in developing an improved approach to accessing the scaffold for future structure-activity relationship screening and demonstrating that modern process technologies like flow can also be used routinely to perform fundamental research in a more sustainable and responsible manner. In summary, all six steps were successfully translated into flow and improved yields were shown with the use of greener solvents and operating at unconventionally high temperature and pressures especially when considering the Claisen rearrangement step. Design of experiment was also used in the last two stages which included i) the second allylation which required a strong base such as sodium hydride and was used as a slurry pumping through peristaltic pumps, and ii) the final ring closing metathesis stage in which two ruthenium-based catalysts were investigated with the use of a greener solvent. It was found that the flow approach yielded an overall percentage yield of 37.7 % in 105 minutes, compared to the batch approach that yielded an overall percentage yield of 0.77 % in 154 hours. Council for Scientific and Industrial Research Chemistry Dissertation (MSc (Chemistry))--University of Pretoria,2024. Unrestricted Faculty of Natural and Agricultural Sciences None 2024-03-15T07:46:23Z 2024-03-15T07:46:23Z 2024-09 2024-03 Dissertation * S2024 http://hdl.handle.net/2263/95224 10.25403/UPresearchdata.25403638 en © 2023 University of Pretoria. All rights reserved. The copyright in this work vests in the University of Pretoria. No part of this work may be reproduced or transmitted in any form or by any means, without the prior written permission of the University of Pretoria. application/pdf University of Pretoria |
| spellingShingle | UCTD Flow chemistry, Claisen rearrangement, Ring closing metathesis, 8-membered ring, benzo-fused heterocycle Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies |
| title | Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies |
| title_full | Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies |
| title_fullStr | Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies |
| title_full_unstemmed | Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies |
| title_short | Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies |
| title_sort | synthesis of an 8 membered oxygen containing benzo fused heterocycle using flow technologies |
| topic | UCTD Flow chemistry, Claisen rearrangement, Ring closing metathesis, 8-membered ring, benzo-fused heterocycle |
| url | http://hdl.handle.net/2263/95224 |