A Diversity-Oriented Synthesis Approach to Functionalized Azaheterocycles using Cyclic Alpha-Halo Eneformamides
Date of Degree Completion
Master of Science (MS)
Timothy K. Beng
Second Committee Member
Third Committee Member
Functionalized piperidines, azepanes, azamacrocycles, morpholines, and thiomorpholines are common structural motifs found in a wide range of pharmaceuticals such as carmegliptine, levofloxacin, thioridazine, claviciptic acid, and azithomycin. As a result, there is a strong desire to construct highly functionalized nitrogen-bearing ring scaffolds in order to construct a wide range of drug possibilities. There are several non-modular and step-uneconomical synthetic methods used in the construction of these aforementioned motifs such as ring closing metathesis, ring expansions, and intramolecular reductive amination. In this research, we present a step-economical, cost-effective, scalable, and diversity-oriented synthesis approach to highly functionalized N-heterocycles through the intermediacy of α-halo enamines/enamides. The synthetic utility of the method is exemplified through the construction of quaternary cyclic propargylic and homoallylic amines, polycyclic lactams, as well as chiral dihydro 1,4-oxazines and thiazines. Given the generality of the approach, we are confident that the synthesis and medicinal chemistry communities will undoubtedly embrace it, thus, endowing it with a practical advantage over existing methodologies.
Langevin, Spencer A., "A Diversity-Oriented Synthesis Approach to Functionalized Azaheterocycles using Cyclic Alpha-Halo Eneformamides" (2017). All Master's Theses. 779.
Heterocyclic Compounds Commons, Macromolecular Substances Commons, Medicinal and Pharmaceutical Chemistry Commons, Organic Chemicals Commons, Organic Chemistry Commons, Other Chemicals and Drugs Commons, Pharmaceutical Preparations Commons, Pharmaceutics and Drug Design Commons, Polycyclic Compounds Commons