Synthesis and Studies of 9-Activated 4,5-Dimethoxyacridine Multifunctionalizable Building Blocks

Abstract

9-Substituted-4,5-bifunctionalized acridines are common subunits of numerous drugs and fluorescent dyes, thus studies were carried out on a series of their potential precursors from the aspect of preparation, reactivity, chemical stability and potential applications. The syntheses of the new 9-fluoro-, 9-triflate and 9-lithiated derivatives of 4,5-dimethoxyacridine were reported. All the new intermediates supplemented with the recently synthetized 9-haloacridine analogues were compared and their applicability was discussed. The reactivity of the studied acridino-precursors was tested by using them as starting materials in Suzuki-Miyaura and Kharasch type cross-couplings as well as in Li-organic reactions.