Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies - an exercise in undertaking research with sustainability as a driver
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Royal Society of Chemistry
Abstract
Due to their natural abundance and biological properties, benzo-fused heterocycles are attractive targets in the field of drug discovery. Previously, a synthetic strategy for accessing 5-, 6-, 7- and 8-membered oxygen-containing benzo-fused heterocycles with the oxygen atom in the less commonly encountered 2-position was reported, however, the approach was hindered by long reaction times and a reliance on high boiling point solvents such as DMF. Targeting an 8-membered analogue as an exemplar, we highlighted that the adoption of basic green chemistry principles coupled with the use of flow chemistry techniques could be utilised (with limited development time) to improve day-to-day sustainability when performing synthetic research. In the case in hand, several key improvements were noted including (i) a higher overall yield (37% vs. 26%), (ii) a significantly reduced reaction time (110 min vs. 136 h) and (iii) the avoidance of the undesirable solvent DMF.
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DATA AVAILABILITY : The data supporting this article have been included as part of the Supplementary Information.
Keywords
Benzo-fused heterocycles, Drug discovery, Sustainability, Flow technologies,, Green chemistry
Sustainable Development Goals
SDG-12: Responsible consumption and production
Citation
Currie, B.M., Neyt-Galetti, N.C., Olivier, T. et al. 2025, 'Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies - an exercise in undertaking research with sustainability as a driver', RSC Sustainability, vol. 3, no. 3, pp. 1356-1365, doi : 10.1039/d4su00528g.