Organic methodology development is focused on finding new ways to prepare organic compounds. Multicomponent coupling reactions (MCRs) are efficent one-pot methods to rapidly assemble complex organic scaffolds. Isocyanide-based MCRs (IMCRs) are an important subclass of MCRs, due to the structural capability of isocyanides to form peptide-like products.
An Ugi-Smiles reaction is an IMCR in which a phenol, amine, aldehyde, and isocyanide are combined to form a complex amide structure. Combination of IMCRs with other reactions, through a tandem reaction process, can provide access to diverse drug-like compounds.
Recently, a tandem Ugi-Smiles Intramolecular Diels-Alder (US-IMDA) was observed, in which an Ugi-Smiles coupling was immediately followed by an intramolecular Diels-Alder cycloaddition, leading to the formation of epoxyisoindolines.
This work describes the expansion of the tandem US-IMDA process, through investigation of heterocyclic phenols as reaction components. Optimization studies provide insight into the scope and mechanism of the reaction and the stereochemistry of the final products. These modifications have led to the production of a small library of heterocycle-derived epoxyisoindoline compounds
|Advisor:||Luesse, Sarah B.|
|Commitee:||De Meo, Cristina, Dixon, Robert|
|School:||Southern Illinois University at Edwardsville|
|School Location:||United States -- Illinois|
|Source:||MAI 58/01M(E), Masters Abstracts International|
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