The Synthesis of Novel Isoindoline Nitroxides Bearing Water-Solubilising Functionality

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 12; pp. 1902 - 1915
• Main Authors: Fairfull-Smith, Kathryn E., Brackmann, Farina, Bottle, Steven E.
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.04.2009; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Antioxidant; Chemistry; Chemistry, Organic; Exact sciences and technology; Free radicals chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Isoindoline; Medicinal chemistry; Nitroxide; Organic chemistry; Physical Sciences; Preparations and properties; Radicals; Reactivity and mechanisms; Science & Technology; Medicinal chemistry; Isoindoline; ANTIOXIDANTS; TEMPOL; NITRIC-OXIDE; Nitroxide; Antioxidant; Radicals; FREE-RADICALS; Water; Nitroxyl; Molecular structure; Nitrogen heterocycle; Alcohol; Steric hindrance; Isoindole derivatives; Chemical reduction; Amine; Carboxylic acid; Steric effect; Organic free radical; Analog; Aromatic compound; Oxidation; Phosphonic acid derivatives; Chemical synthesis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200801255

A range of novel tetramethyl‐ and tetraethylisoindolinenitroxides, possessing aryl‐linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindolines was not easily transferred to the corresponding tetraethylisoindoline system. Instead, various tetraethylisoindoline analogues were accessed by the oxidation of methyl groups attached to the aromatic ring to give the carboxylic acids. The increased steric bulk of the tetraethyl structures should limit bio‐reduction and these compounds may have potential as antioxidants.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) A number of novel tetramethyl‐ and tetraethylisoindoline nitroxides possessing water‐solubilising functionalities were synthesised. The increased steric bulk of the tetraethyl structures should limit bio‐reduction and these compounds may have potential as antioxidants.