Date of Graduation
Eberly College of Arts and Sciences
Bjorn C. G. Soderberg.
Using a palladium-catalyzed reductive N-heteroannulation method previously discovered in our labs, a 20 mmol synthetic route to methyl indole-4-carboxylate has been developed. Methyl indole-4-carboxylate is synthesized in four steps, with the key step being the reductive cyclization of methyl 2-ethenyl-3-nitrobenzoate in good overall yield. This cyclization method has been modified and applied to the preparation of quinoxalines, 2-quinoxalinones and other heterocyclic compounds. We also propose a possible mechanism for these transformations.;In addition, a novel method to 2-alkylbenzimidazoles has been developed. The thermal reaction of 2-azidonitrobenzenes and various aldehydes give 2-alkylbenzimidazoles generally in moderate yield.
Wallace, Jeffery M., "Novel syntheses of indoles, quinoxalines, 2-quinoxalinones, 2-alkylbenzimidazoles and other heterocycles" (2003). Graduate Theses, Dissertations, and Problem Reports. 1945.