Author ORCID Identifier
https://orcid.org/0000-0001-8302-0493
Date of Award
8-31-2026
Document Type
Open Access Thesis
Degree Name
Doctor of Philosophy (PhD)
Department
Chemistry/Organic Chemistry
First Advisor
Wei Zhang
Abstract
Efficient synthesis of novel heterocycles with biological interest remains a challenge in modern organic chemistry. This dissertation presents the development of efficient synthetic strategies that combine multicomponent reactions (MCRs) with sequential reactions for rapid access a diverse array of polyheterocyclic compounds. The projects are: 1) Groebke-Blackburn-Bienaymé (GBB) reaction followed by N-acylation and Friedel-Crafts (FC) cyclization for the construction of imidazopyridine- and indole-fused azepinones involving an unusual ring-expansion process. 2) Modified GBB condensation products for intramolecular Diels-Alder (IMDA) cycloaddition and dehydrative re-aromatization to access imidazopyridine-fused isoquinolinones. 3) Integration of the Ugi-three component reaction (Ugi-3CR) and Pictet-Spengler (PS) reaction followed by ring-expansion for regioselective synthesis of imidazopyridine-fused azocinos. 4) Ring-opening of GBB condensation products by Selectfluor-mediated oxidative dearomation for the synthesis of α-iminonitriles. In all these projects, density functional theory (DFT) calculations were used to predict the thermodynamically favored product and the regioselectivity of the products. This statement works if you only calculated ground state energies of reactants/intermediates/products as it only refers to the thermodynamic factors and not any kinetic favorability.
Recommended Citation
Nath, Ashutosh, "Multicomponent Reaction-Initiated Synthesis of Polyheterocyclic Compounds" (2026). Graduate Doctoral Dissertations. 1216.
https://scholarworks.umb.edu/doctoral_dissertations/1216
Comments
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