Title:
Exploring Acceptor-Acceptor Metal Carbenes in The Synthesis of Nitrogen Heteroaromatic Scaffolds
Exploring Acceptor-Acceptor Metal Carbenes in The Synthesis of Nitrogen Heteroaromatic Scaffolds
Author(s)
Guerra Faura, Gabriel
Advisor(s)
France, Stefan
Gutekunst, Will R.
Gutekunst, Will R.
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Abstract
Due to their ubiquitous presence in bioactive molecules, the development of new methodologies for the synthesis of nitrogen heteroaromatic scaffolds is key to the field of organic chemistry. In this thesis, acceptor-acceptor metal carbenes derived from diazo compounds were utilized in the development of synthetic methodologies that allow for the modular synthesis of nitrogen heteroaromatic compounds. First, a chemodivergent synthesis of DHF acetals and highly-substituted indoles was accomplished by utilizing pyrrolyl-alpha-diazo-beta-ketoesters and enol ethers in the presence of metal-catalysts. The development of this methodology led to the synthesis of several indole derivatives which were evaluated for potential cyclooxygenase (COX) inhibition and anti-cancer activities. By exploring the reactivity of indolyl-substituted alpha-diazo-beta-ketoesters and alpha-diazo-beta-ketonitriles, the synthesis of highly-substituted carbazoles, indolo[2,3-a]carbazoles and furo[2,3-b]indoles was also accomplished.
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Dissertation