Regioselective Photocycloaddition of Saccharin. Continuous Flow Synthesis of Benzosultams and Theoretical Study

GABRIELA OKSDATH MANSILLA; FRANCISCO FIGÜEROA; JUAN E. ARGUELLO; DIEGO SAMPEDRO

Köln

Simposio; 20th European Symposium on Organic Chemistry (ESOC 2017); 2017

University of Cologne, Germany, Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society)

Benzosultams are heterocyclic sulfonamide compounds which are important pharmaceuticals with a broad spectrum of biological activities. In particular, saccharins already have the sulfonamide functionality in the heterocyclic system and it has been shown diverse biological activities. In addition, ring-expanded saccharin derivative such as oxicams is used as an anti-inflammatory drug.[1]Due to the biological importance of benzosultams, the development of different synthetic approach is of great interest to organic and medicinal chemists. In this context, synthetic organic photochemistry constitutes a research area which could be obtained natural products as well as molecules with high structural complexity, in a simple and efficient way.In particular, there are few reports about photochemistry saccharins study with synthetic application. [2] Recently, in our group photocyclizations of N-(thioalkyl)-saccharins were carried out obtaining different polycyclic sultams in good yields. These results motivate us to continue exploring photo-reactivity of saccharin with synthetic applications.[3]Taking into account the similitude of saccharin with phthalimide and in fact to phthalimides derivative can be participated in different photoreactions and used it in the synthesis of heterocyclic compounds with new rings; we decide carried out the photocycloaddition of saccharin with -methyl-styrene to evaluated the best condition to obtaining benzosultam 1Additionally, we report a photocycloaddition study of saccharin anion with different electron-rich systems. We evaluated the benzosultams photo-generation in flow system and theoretical studies were developed by way of decide the regioselectivity observed.