Synthesis of Chromenopyridines with the New All-Carbon Quaternary Centre

Charles University in Prague Faculty of Pharmacy in Hradec Králové Candidate: Patrik Sedláček Supervisor: PharmDr. Petr Matouš, Ph.D. Title of thesis: Synthesis of Chromeno[3,4-c]pyridines with New All-Carbon Quaternary Centre This diploma thesis focuses on the synthesis of 3,4-disubstituted pyridine derivatives and their subsequent cyclization to form chromeno[3,4-c]pyridine derivatives with a new all-carbon quaternary center. Phenyl-propiolate reacts with an aryl-substituted propargyl amine protected with 4- methoxybenzenesulfonyl group to form a 1,5-enyne. Substituted 1,5-enyne undergoes intramolecular cyclization catalyzed by tri(2-furyl)phosphinogold(I)chloride [AuCl(TFP)] to form the corresponding dihydropyridine. In the presenece of concentrated H2SO4, dihydropyridine undergoes carbocyclization forming the corresponding chromenopyridine with a new all-carbon quaternary center. The compounds prepared and their derivatives could find application as potentially biologically active substances and intermediates in organic synthesis.