Document Type

Thesis

Date of Degree Completion

Spring 2017

Degree Name

Master of Science (MS)

Department

Chemistry

Committee Chair

Dr. Timothy K. Beng

Second Committee Member

Dr. Levente Fabry-Asztalos

Third Committee Member

Dr. Gil Belofsky

Abstract

The synthesis and evaluation of structure-activity relationships of saturated nitrogen heterocycles is the focal point of various pharmaceutical companies thanks to the high biological activity of previously isolated azacycles. Here, we describe an operationally simple and highly efficient approach to macrocyclic lactams bearing vicinal stereocenters and a challenging cycloalkyne motif. The outcomes are achieved through a novel [4 + 2] cycloaddition reaction between an N-iodoarylated-1,3-azadiene and cyclic anhydrides, followed by interception of the cycloadducts in cross-coupling manifolds (e.g., Sonogashira coupling) and concomitant lithiation-cyclization of the tethered alkyne. An unprecedented example of a hydroamino alkylation that is transition metal-free and occurs at room temperature will also be discussed.

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