Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
Manel Vega, Luis Martínez‐Crespo, Miquel Barceló‐Oliver, Carmen Rotger, Antoni Costa
Abstract
Simple, clean and fast photoconversion of aniline-derived squaramides was achieved by flashlight illumination. UV irradiation enabled the photochemical squaramide ring-opening to generate 1,2-bisketenes, which DMSO trapped as the nucleophilic oxidant. The only photoproducts isolated were 3,4-arylamino maleic anhydrides, which present conformational preferences very different from those of their parent squaramides. Similar photoconversion was achieved in MeOH. The UV-mediated time-dependent anion transport inhibition was demonstrated, establishing a new approach for modulating the transport abilities of AD-squaramides.
Topics & Concepts
SquaramideChemistryAnilineNucleophileIonCombinatorial chemistryCatalysisOrganic chemistryOrganocatalysisEnantioselective synthesisSynthesis and Catalytic ReactionsRadical Photochemical ReactionsSynthesis of Indole Derivatives