Within this contribution the synthesis of anilino-substituted bithiazoles as potentially bioactive compounds is reported. The key chemical transformations in the applied synthetic strategy were Pd-catalyzed cross coupling reactions which were used for the formation of various bithiazoles. Different cross coupling methodologies were investigated. Starting from 2-thiazolamine the desired metal organyls were prepared in two steps. Besides the well documented Stille and Negishi reaction on thiazole derivatives, a new method could be established. After successful preparation of the first thiazoleboronic acid ester, Suzuki-Miyaura reactions were performed. Upon reaction with various bromo-thiazoles the desired bithiazole derivatives were obtained, whereby the Stille reaction gave the best results compared to the other two methods. Subsequently the chloro atom was used for a nucleophilic exchange reaction with aniline derivatives to give the target compounds.
Michael Schnürch studierte Technische Chemie an der TU-Wien wo er2001 sein Diplomstudium sowie 2005 sein Doktoratsstudium imFachbereich Organische Chemie abschloss. Anschließend verbrachteer ein Postdoc Jahr an der Columbia University in New York City.Seit Ende 2007 ist er Habilitant am Institut für AngewandteSynthesechemie der TU-Wien.