Využití zlatného katalyzátoru při syntéze substituovaných pyridinů

• Main Author: Janoušek, Martin
• Other Authors: Špulák, Marcel
• Format: Dissertation
• Language: Czech
• Published: 2016
• Online Access: http://www.nusl.cz/ntk/nusl-351476

Charles University in Prague Faculty of Pharmacy in Hradec Králové Department of Inorganic and Organic Chemistry Candidate: Martin Janoušek Supervisor: PharmDr. Marcel Špulák, Ph.D. Title of thesis: The synthesis of substituted pyridines employing gold(I) catalyst This work is focused on the preparation of 3,4-disubstituted pyridine derivatives. MBS- protected propargylamine and MS-protected 1-ethynylcyklohexylamine provide with methyl propiolate to form appropriate 1,5-enyne, which undergoes Sonogashira coupling with various aryl iodides. Substituted enyne is subjected to cyclization yielding appropriate tetrahydropyridine in the presence of catalyst tris(2-furyl)phosphinegold(I) chloride. Derivate substituted by pentamethylen-1,5-diyl didn't cyclize. Deprotection leads to the preparation of substituted pyridines, which could serve as an intermediates in organic synthesis or potentially with biological activity. Keywords: gold catalysis, enyne cyclization, pyridine derivatives