Tomé, SaraPatoilo, DianaSantos, Clementina M.M.Silva, Artur2013-03-122013-03-122012Tomé, Sara; Patoilo, Diana; Santos, Clementina M. M.; Silva, Artur (2012). Synthesis of Benzo[a]naphtho[2,3-c]xanthones from 2-styrylchromones. In 3º Encontro Nacional de Química Terapêutica. Aveirohttp://hdl.handle.net/10198/82412-Styrylchromones, a small group of natural occurring chromones vinylogues of flavones (2-phenylchromones) have been ex tensively studied (both by synthesis and transformations)111 due to their known important biological activities. 121 Following our interest in 2-styrylchromones and exploiting its reactivity as synthons in the preparation of other type of compounds, we studied their reactivity as dienophile in the Diels-Alder reaction with ortho-benzoquinodimethanesY1 Another field of interest of our research group is the chemistry of xanthones. 141 This class of oxygen-containing heterocyclic compounds is also associated with a broad spectrum of pharmacological propertiesY1 The interesting biological profile of benzoxanthones 161 is an example that the tricyclic core of xanthones may represent a promising key in medicinal chemistry. In this communication we present a route towards the synthesis of benzo[a]naphtho[2,3-c]xanthones from 2-styrylchromones. Here we discuss the experimental procedures and reaction mechanisms of the Diels-Alder transformation of 2-styrylchromone 1 into the oxidized cycloadduct 3 and its subsequent photoinduced electrocyclization and oxidation that gave access to the desired benzo[a] naphtho[2,3- c]xanthone 4.engconference object