Synthesis of novel heteropolycyclic systems via mannich reaction
LE3 .A278 2020
2020
Jha, Amitabh
Acadia University
Bachelor of Science
Honours
Chemistry
Heterocycles are known for their use in agricultural industries,and drug design in the pharmaceutical industry. They can be found in nature in structures such as coenzymes and vitamins. They have also been used as antioxidants. It is imperative to design novel heterocyclic systems in short synthetic pathways to minimize time and costs, but also to maximize efficiency in the synthetic scheme.The purpose of this research is to design a synthesis for a heterocyclic system, which allows for multiple bond formation in a single step. By rational design, analogues of a tetracyclic framework were investigated that employ Mannich reaction on 2-naphthols with t-butyl carbamate, deprotection of the carbamate group, followed by one-pot N/O-acetal and amide formation reactions with a keto-acid. Seven heterocyclic analogues were synthesized with the same bearing tetra/pentacyclic framework, by varying the phenol, aldehyde and keto-acid. The novel analogues were purified using column chromatography and methanol washes. NMR spectroscopy and HRMS were used for characterization.
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https://scholar.acadiau.ca/islandora/object/theses:3404
