Applications of technologies and synthetic methodologies developed under continuous flow conditions at LQBO-UFSCar for the preparation of molecules with biological activities and APIs

Abstract

In this research project we propose the application of the methodologies recently developed in our research laboratory (LQBO-UFSCar) for the synthesis of bioactive molecules and active pharmaceutical ingredients (APIs) such as (-) - aritasone, favipiravir, and ibuprofen. For these syntheses, we will use continuous flow reaction systems, and simple solutions also developed in our laboratory. This project is divided into 3 subprojects (Figure i). In the first (Project 1) we will apply the photooxygenation system working under continuous flow regime for the synthesis and scale-up of (-) - pinocarvone. Then, we will study the synthesis of (-) - aritasone through the hetero-Diels-Alder reaction under extreme conditions (high temperature and pressure). In the second (Project 2) we will invest efforts for the synthesis of favipiravir using continuous photocatalyzed reaction conditions and thermal protocols to obtain this API in a few steps and low cost. We emphasize that this proposed synthesis has unprecedented steps concerning the syntheses described in the literature, namely a photocatalytic fluorination step which we intend to develop. Similarly, in the last subproject (Project 3), we intend to develop a synthesis of ibuprofen, which is a well-known and relatively low-cost API, but still deserves more advantageous synthetic investigations. In this case, we will apply a photocatalytic step developed in our group that uses diazonium salts and porphyrin derivatives (0.5mol%) as photocatalysts (single electron transfer). In general, we envisioning the appreciation of many results from our team applying the developed solutions in the synthesis of relevant molecules. It is worth mentioning that this project is aligned with the top 10 technologies and current demands of our society, giving a relevant opportunity to students as well as valuable training in flow chemistry, which is a well-required skill by the current job market. (AU)