Ferreira, Lucas Coral;
De Souza Galaverna, Renan;
McBride, Tom;
Costa e Silva, Rodrigo;
Browne, Duncan L;
Pastre, Julio Cezar;
(2025)
Fast and scalable continuous flow synthesis of butenolides and coumarins.
Reaction Chemistry and Engineering
10.1039/d4re00567h.
(In press).
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Abstract
Herein, we present a versatile and efficient continuous flow protocol for the synthesis of structurally diverse butenolides and coumarins through the in situ generation of acylketenes via the retro hetero-Diels–Alder reaction of dioxinones with α-hydroxy-ketones and salicylaldehydes, respectively. This protocol enabled the synthesis of 5 examples of butenolides with yields ranging from 30 to 91% and 16 examples of coumarins with yields ranging from 30 to 99%. The versatility and practicality of the protocol were demonstrated by the gram-scale synthesis of a biologically relevant γ-spiro butenolide core, as well as the production of benzo-coumarins. Modern medicinal chemistry demands both scalability and the ability to synthesize structurally diverse compounds in a single synthetic platform, and our methodology effectively addresses these challenges in a fast and safer manner.
| Type: | Article |
|---|---|
| Title: | Fast and scalable continuous flow synthesis of butenolides and coumarins |
| DOI: | 10.1039/d4re00567h |
| Publisher version: | https://doi.org/10.1039/d4re00567h |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10205266 |
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