Date of Award
2015-01-01
Degree Name
Master of Science
Department
Chemistry
Advisor(s)
Katja Michael
Second Advisor
Shizue Mito
Abstract
p-Indolequinones are important heterocycles since they display interesting bioactivities such as anticancer activities as well as the ability to trigger drug release in drug targeting research. Additionally, they are also useful in precursors for the synThesis of bioactive compounds. Over decades, many methodologies have been investigated for the synThesis of p-indolequinones. Among those, cyclization of quinones plays an important role in convenient synThesis of these compounds. However, the great majority of these methods only describe quinones as electrophiles in cyclization. In our research, we found an intramolecular nucleophilic attack of quinone to an in-situ generated carbonyl group and developed a new methodology for benzofused p-indolequinones synThesis in one-pot.
Moreover, a selective debenzylation of tertiary amines using a non-metal reagent was also explored. Metal complexes have been dominantly used for N-dealkylation of amines. However, they resulted in low selectivity of debenzylation over dealkylation as well as the process of disposing heavy metals. Non-metal reagents, on the other hand, are efficient in debenzylating mostly secondary amines. For the first time, the attack of tertiary amine to Dess-Martin periodinane was discovered in our work and was developed as a selective method to deprotect benzyl group of tertiary amines.
Language
en
Provenance
Received from ProQuest
Copyright Date
2015
File Size
159 pages
File Format
application/pdf
Rights Holder
Quang Huynh Luu
Recommended Citation
Luu, Quang Huynh, "SynThesis of Benzofused-p-indolequinones from 1,4-naphthoquinone and selective N-Debenzylation by Dess-Martin Periodinane" (2015). Open Access Theses & Dissertations. 885.
https://scholarworks.utep.edu/open_etd/885