The Synthesis of Biologically Active Core Structures Using Electrophilic Cyclization and Palladium-Catalyzed Annulation

Author

Eli Sidman, Bard CollegeFollow

Date of Submission

Spring 2012

Academic Program

Chemistry

Project Advisor 1

Tanay Kesharwani

Abstract/Artist's Statement

The synthesis of biologically active core structures such as indoles, imidazoles and pyrrolo-[2,1-j]quinolines can be achieved using known methodologies including electrophilic cyclization and the Larock indole synthesis. The Larock indole synthesis was performed in order to create a pyrrolophenanthridinone core structure through the annulation of alkynes. Initial investigations into the synthesis of pyrrolophenanthridinone afforded pure compounds in lower yields than other previously published methodologies. Pyrrolo-[2,1-j]quinoline derivatives were formed in high yields using electrophilic cyclization and subsequent palladium-catalyzed cross coupling reactions such as Suzuki and Sonogashira coupling, which were employed to form biologically active analogues. Functionalization of a pyrrolo-[2,1-j]quinoline core using Sonogashira coupling failed while Suzuki coupling has proven to be effective. Attempts to synthesize bicyclic derivatives of imidazole core structures, such as thiophene-fused imidazoles, using electrophilic cyclization were unsuccessful.

Distribution Options

Access restricted to On-Campus only

Creative Commons License

This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

Recommended Citation

Sidman, Eli, "The Synthesis of Biologically Active Core Structures Using Electrophilic Cyclization and Palladium-Catalyzed Annulation" (2012). Senior Projects Spring 2012. 86.
https://digitalcommons.bard.edu/senproj_s2012/86