Teresa Mancilla, Lourdes Carrillo, L. Zamudio-Rivera
Aug 1, 2001
Citations
2
Influential Citations
19
Citations
Journal
Organic Preparations and Procedures International
Abstract
Some isoindolines are important intermediates for the syntheses of novel multidrug resistance reversal agents;' they have also shown antiinflammatory'-4 and diuretic activity.5," They have been used for treating coronary vessel disease^^,^ and evaluated as alpha-adrenergic and adrenergic neuron blocking agents.9 2-Substituted isoindolines have been prepared by a) alkylation of isoindob) alkylation and reduction of ph tha l imide~~.~~ '~ ' and c) cyclocondensation of a&-dibromo-oxylene with primary amine~.'"~.' '. ' ' To our knowledge, there are no reports concerning the synthesis of 2-substituted isoindoline derivatives of a-amino acids, which could have important biological properties and be used as ligands to obtain organometallic compounds with antitumor properties.'' Our current interest in 2-substituted isoindoline 4 derivatives of a-aminoacids prompted us to develop an easy methodology to obtain them from a-amino acid methyl ester hydrochlorides 2 and a,a'-dibromoo-xylene. This paper describes the synthesis and characterization by spectroscopic methods of six new 2-substituted isoindolines 4a-f. The structure of compound 4b was further established by a singlecrystal X-ray diffraction study.