Kemp, Aiden, Durand, Marine, Wall, Daniel, Szieber, Peter, Hermanns, M. Iris, and Oelgemoeller, Michael (2024) Synthesis of 1H‑isoindolin‑1‑ones via a simple photodecarboxylative addition of carboxylates to phthalimides and evaluation of their antibiotic activity. Photochemical & Photobiological Sciences, 23. pp. 1353-1360.

Preview

PDF (Published Version) - Published Version Available under License Creative Commons Attribution. Download (780kB) | Preview

Abstract

A variety of 3-hydroxy-isoindolin-1-one derivatives were synthesized using the photodecarboxylative addition of carboxylates to phthalimide derivatives in aqueous media. Subsequent acid-catalyzed dehydration furnished 3-(alkyl and aryl) methyleneisoindolin-1-ones with variable E-diastereoselectivity in good to excellent overall yields. Noteworthy, the parent 3-phenylmethyleneisoindolin-1-one underwent isomerization and oxidative decomposition when exposed to light and air. Selected 3-hydroxy-isoindolin-1-one and 3-(alkyl and aryl)methyleneisoindolin-1-one derivatives showed moderate antibacterial activity that justifies future elaboration and study of these important bioactive scaffolds.

Item ID:	83624
Item Type:	Article (Research - C1)
ISSN:	1474-905X
Keywords:	Photodecarboxylation, Phthalimides, Photo-induced electron transfer, Isoindolinones, Antibiotic activity
Copyright Information:	© The Author(s) 2024. Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
Funders:	Hochschule Fresenius
Projects and Grants:	Forschungsförderung 1 program 2023
Date Deposited:	17 Sep 2024 01:16
FoR Codes:	34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340503 Organic chemical synthesis @ 60% 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340505 Physical organic chemistry @ 40%
SEO Codes:	28 EXPANDING KNOWLEDGE > 2801 Expanding knowledge > 280105 Expanding knowledge in the chemical sciences @ 100%
Downloads:	Total: 9 Last 12 Months: 9
	More Statistics