Continuous Flow Photochemical Synthesis of 3-Methyl-4-arylmethylene Isoxazole-5(4H)-ones through Organic Photoredox Catalysis and Investigation of Their Larvicidal Activity

Autor:	Ana Beatriz S. Sampaio, Mônica Shigemi S. Mori, Lorena C. Albernaz, Laila S. Espindola, Carlos Eduardo M. Salvador, Carlos Kleber Z. Andrade
Rok vydání:	2023
Předmět:	isoxazolone larvicidal activity photochemistry continuous flow Physical and Theoretical Chemistry Catalysis General Environmental Science
Zdroj:	Catalysts Volume 13 Issue 3 Pages: 518
ISSN:	2073-4344
Popis:	Isoxazole-5(4H)-ones are heteropentacycle compounds found in several bioactive molecules with pharmaceutical and agrochemical properties. A well-known multicomponent reaction between β-ketoester, hydroxylamine, and aromatic aldehydes leads to 3-methyl-4-arylmethylene isoxazole-5(4H)-ones, in mild conditions. The initial purpose of this work was to investigate whether the reaction might be induced by light, as described in previous works. Remarkable results were obtained using a high-power lamp, reducing reaction times compared to methodologies that used heating or catalysis. Since there are many examples of successful continuous flow heterocycle synthesis, including photochemical reactions, the study evolved to run the reaction in flow conditions and scale up the synthesis of isoxazolones using a photochemical reactor set-up. Eight different compounds were obtained, and among them, three showed larvicidal activity on immature forms of Aedes aegypti in tests that investigated its growth inhibitory character. Mechanistic investigations indicate that the reactions occur through organic photoredox catalysis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ddc55b9a9a7c52a22e7ca89cbf103aa4 https://doi.org/10.3390/catal13030518 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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