Pharmacology, Toxicology and Environmental Health Commons^™

New Approaches To Heterocycle Synthesis: A Greener Route To Structurally Complex Protonated Azomethine Imines, And Their Use In 1,3-Dipolar Cycloadditions, Ram Chandra Dhakal

Graduate College Dissertations and Theses

1-Aza-2-azoniaallene salts are reactive intermediates that undergo [3+2] cycloaddition with many different types of multiple bonds. For the past several years, the Brewer group has studied the reactivity of these intermediates in intramolecular reactions, and have discovered that these cationic heteroallenes can react through a variety of other, mechanistically distinct, pathways to give different classes of nitrogen heterocycles. For example, prior work in the Brewer group revealed that 1-aza-2-azoniaallene salts could react in an intramolecular [4+2] cycloaddition reaction to give protonated azomethine imine salts containing a 1,2,3,4-tetrahydrocinnoline scaffold. Further study of the scope and limitations of this Diels-Alder-like reaction are …