Honors Theses

Date of Award

Spring 5-2-2021

Document Type

Undergraduate Thesis

Department

Chemistry and Biochemistry

First Advisor

Hoang V. Le

Relational Format

Dissertation/Thesis

Abstract

The inverse electron demand Diels−Alder cycloadditions of heterocyclic azadienes have provided a robust methodology for synthesizing highly substituted and functionalized heterocycles. It is widely used in organic synthesis and the pharmaceutical industry in the divergent construction of screening libraries and bioorthogonal conjugation. Each heterocyclic azadiene was found to possess a unique reactivity toward different classes of dienophiles, display predictable modes of cycloaddition, and exhibit substantial substituent electronic effects impacting their intrinsic reactivity and cycloaddition regioselectivity. Synthesis of 1,2,4,5-tetrazine has been reported in the literature since the late 19th century, showing scientists' tremendous interest in its application.

Herein we attempt to synthesize the 1,2,3,5-tetrazine, which is the less popular member of the family. Initial studies of its cycloaddition reactivity, stability, and scope illustrate that it displays similar properties to that of the isomeric 1,2,4,5-tetrazine. The lack of scientific focus on the compound despite its potential value has motivated us to develop an efficient synthetic route via N-methylene amide and azide cycloaddition. Although the attempt to prepare the desired tetrazine was unsuccessful, our designed method interestingly led up to a hydrolysis pathway that allowed us to explore the application of sodium azide further.

Creative Commons License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.

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