2015 REU Poster: Synthesis of New Scaffolds via Bisalkyne Cyclizations Catalyzed by Triflic Acid
Duque, Jaime Alvarez
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The need for novel synthesis methods for the creation of unique molecular scaffolds is a present-day topic in medicinal chemistry. Current methods of drug discovery rely largely on an economical approach, biasing the efforts of synthesis to the creation of facile or pre-explored scaffolds. Diversity-oriented synthesis seeks to reverse this trend by facilitating the preparation of complex molecules. Building on a diversity-oriented approach, the synthesis of Indenopyridene scaffolds from 1,6 N-tethered diynes was explored. The construction of the scaffold is achieved through a novel acid-catalyzed cycloisomerization/Friedel-Crafts mechanism, leading to a heterocyclic three-ring system. The effect of substituents on the bisalkyne precursors, as well as reaction conditions such as temperature and concentration, were analyzed. Findings suggest that electron-withdrawing substituents tend to facilitate product formation, while electron-donating groups hinder the reaction. A trend in concentration and temperature also seems to be present, indicating that decreasing these parameters results in increased product yield. The reaction provides an easily diversifiable heterocyclic scaffold, and may prove to be a useful tool in both synthetic organic chemistry and medicinal chemistry.
Poster presentation at REU Summer's End Research Symposium, 2015, by REU participant Jaime Alvarez Duque, Miami Dade Community College - John Snyder group, Kyle Strom lab mentor.