Publication Date

2026

Document Type

Dissertation/Thesis

First Advisor

Hagen, Timothy J.

Second Advisor

Klumpp, Douglas A.

Degree Name

Ph.D. (Doctor of Philosophy)

Legacy Department

Department of Chemistry and Biochemistry

Abstract

Spirocycles are important scaffolds with a wide range of applications in material science as well as in medicine. The introduction of a heteroatom into the spirocyclic framework can improve its electronic, photophysical, and structural properties. Various reports have been published on the incorporation of atoms other than carbon into the spirocycle. The work outlined in this dissertation involves the development of synthetic methodologies for the synthesis of hetero-spirocycles via superacid-promoted cyclization reactions. These concepts are summarized in Chapter 1.

Chapter 2: Aromatic imines were prepared from 9-fluorenone and azafluorenones, and these substrates were reacted in the Brønsted superacid, triflic acid, to produce good yields of nitrogen-containing spirocycles. The proposed mechanism suggests the involvement of dicationic, superelectrophilic intermediates. The resulting spirocycles may be easily functionalized at the NH positions to prepare amides, sulfonamides, and other derivatives.

Chapter 3: Spirooxindoles are important organic compounds with a wide range of biological activities. A method for making spirooxindoles through superacid-promoted cyclization of imines is described. The imines were first prepared through the condensation of an amine with isatins, followed by a cyclization reaction in superacid media to form the desired spirooxindoles in good yields.

Extent

202 pages

Language

en

Publisher

Northern Illinois University

Rights Statement

In Copyright

Rights Statement 2

NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.

Media Type

Text

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