Synthesis of an 8-membered oxygen-containing benzo-fused heterocycle using flow technologies – an exercise in undertaking research with sustainability as a driver.

Due to their natural abundance and biological properties, benzo-fused heterocycles have been regarded as attractive targets in drug discovery. A synthetic strategy for accessing 5-, 6-, 7-, and 8-membered oxygen-containing benzo-fused heterocycles, with the oxygen atom positioned in the less commonly encountered 2-position, was previously reported; however, the approach was limited by long reaction times and the reliance on high-boiling-point solvents such as DMF.

Focusing on an 8-membered analogue as an exemplar, the application of basic green chemistry principles, in combination with flow chemistry techniques, was demonstrated to improve the day-to-day sustainability of synthetic research, even with minimal development time. In this case, several key improvements were achieved, including (i) a higher overall yield (37% compared to 26%), (ii) a significantly shortened reaction time (110 minutes compared to 136 hours), and (iii) the elimination of the undesirable solvent DMF.

• Currie, B
• Neyt-Galetti, N
• Olivier, T
• Merwe, P
• Dibokwane, L
• Reinhardt, A
• Wyk, L
• Panayides, J
• Riley, D

• Department Chemistry, University of Pretoria, Pretoria, 0028, South Africa

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