Síntese de 3-(organocalcogenil)-imidazotiazinas e funcionalização de inamidas via reações de ciclização, clorosselenação e tosilação promovidas por cloreto férrico e ácido p-toluilssulfônico

Abstract

In this thesis, four synthetic protocols were developed for the synthesis of four new classes of compounds, including the synthesis of 3-(organocalalcogenyl)-benzoimidazothiazines, 4-(organocalalcogenyl)-oxazolones, vinyl tosylates and vinyl selenides. Initially, the electrophilic cyclization of thiopropargyl benzoimidazoles promoted by ferric chloride and diorganoyl diselenides was demonstrated. Through this synthetic methodology, 28 new molecules of 3-(organoselenyl)-imidazothiazines were synthesized with yields from 20 to 90%. Later, in the second part of this work, the reactivity of ynamides against electrophilic selenium species was studied using cyclization and chloroselenation reactions. This methodology led to the formation of 22 examples of 4-(organochalcogenyl)-oxazolones and 10 examples of α-chloro-β-(organochalcogenyl)-enamides with yields from 20 to 84% and 42 to 99%, respectively. Furthermore, further studies demonstrated that the use of ynamides in the presence of p-toluylsulfonic acid led to the formation of vinyl tosylate derivatives (6 examples) with yields from 54 to 94%. Thus, a total of 66 new molecules were synthesized in this work. Finally, to demonstrate the reactivity and versatility of the synthesized compounds, Suzuki and Sonogashira cross coupling reactions were carried out and a new class of products can be obtained.