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UC Riverside UC Riverside Electronic Theses and Dissertations UC Riverside UC Riverside Electronic Theses and Dissertations Title Developing Modular Syntheses of Diverse Nitrogen Heterocycle-Based Compounds for Metal Complexes, Catalysis, and Therapeutics Permalink https://escholarship.org/uc/item/9hz352x2 Author Sterling, Michael David Elliott Publication Date 2019 Peer reviewed|Thesis/dissertation eScholarship.org Powered by the California Digital Library University of California UNIVERSITY OF CALIFORNIA RIVERSIDE Developing Modular Syntheses of Diverse Nitrogen Heterocycle-Based Compounds for Metal Complexes, Catalysis, and Therapeutics A Dissertation submitted in partial satisfaction of the requirements for the degree of Doctor of Philosophy in Chemistry by Michael David Elliott Sterling March 2019 Dissertation Committee: Dr. Catharine H. Larsen, Chairperson Dr. Christopher Switzer Dr. Chia-en Chang Copyright by Michael David Elliott Sterling 2019 The Dissertation of Michael David Elliott Sterling is approved: Committee Chairperson University of California, Riverside DEDICATION To all the people in my life who, without their support, guidance, and love, I would not be where I am today. This section and the following are dedicated to you. First, to my advisor Catharine: thank you for seeing the potential in me, even when I didn’t see it myself. I entered this journey feeling thoroughly unconvinced I could handle it, but your unwavering support and guidance is the reason I am here today. I know it hasn’t been an easy five years by any means, but I wouldn’t rather have taken this trip with anyone but you. I will look back on my time at UCR with pride, as I was fortunate to work for such an amazing chemist, person, and friend. To the members of the Larsen Lab: Zack – I honestly didn’t think I was going to be able to get through this last year without you in the group. Thankfully, your example (both as a chemist and a leader) prepared me better than I could have ever imagined. Keegan – you always knew exactly what to say when I felt things were going off the rails. Your level head, your twisted humor, and your constant availability as a sounding board kept my sanity in the craziest moments. Bobby – I have never seen someone take to research chemistry as quickly and elegantly as you. You have poise, work ethic, and chemical knowledge far beyond your years and I am truly excited to see where your professional life takes you. Jay – just as everyone takes their own path in life, there is no “standard” way to experience graduate school. Whatever you decide to pursue, know this: you deserve to reach your full potential. Don’t sell yourself short into thinking that you can’t do something, because I promise you that you can. To all of you – stay in touch. We share a bond going through this process that is unlike any other relationship, so please reach out – even if only just to catch up on life. iv To Hector: you could have been included in the Larsen Lab, but just like everything you have achieved in the last few years, you deserve special recognition. You are, without a doubt, one of the brightest, kindest, best people I have had the pleasure of knowing in life. Even though our relationship began where I was the mentor and you were the student, that dynamic quickly shifted. We became equals – your advanced knowledge in chemistry and passion for learning allowed us to discuss as peers. At this point, sometimes it feels like I am the one looking up to you: the enthusiasm you have for this subject is infectious and it drives me to be a better chemist. You are destined for greatness, and I am beyond lucky to have experienced your nascency as a scientist. To the family I have made in Riverside: Shane & Stephen, you welcomed me with an open door and open arms. I truly love both of you and am endlessly thankful for your friendship. Dorie, Gary, and Hallie: you didn’t just welcome me into your lives – you embraced me. The love that you have all given me has assuaged the stress in my work life, and for that I cannot express enough gratitude. To my Mom and Lillie: this section is short, not because there isn’t anything to say, but because there aren’t words to encapsulate how important you both are to me. We wouldn’t have made it without each of us, and I love you both to my heart’s capacity. Finally, to Ryan: I wouldn’t be the man I am today without you. You have brought out the best version of myself, believed in me when I didn’t believe in myself, and let me know that I deserve to be excellent. I love you. v ACKNOWLEDGEMENTS The text and results discussed in the following chapters of this dissertation are, in part or in full, a reprint of the material as they appear in the following publications: Chapter 2: Laguna, E. M.; Olsen, P. M.; Sterling, M. D.; Eichler, J. F.; Rheingold, A. L.; Larsen, C. H. Inorg. Chem. 2014, 53 (23), 12231. DOI: 10.1021/ic501965m Chapter 3: Sterling, M. D.; Bishop, L. E.; Nelson, K. G.; Rheingold, A. L.; Larsen, C. H. Dalton Trans. Submitted. I acknowledge the National Science Foundation (CHE-1352665) and the UCR MARCU Star Program for partial support of this research. vi ABSTRACT OF THE DISSERTATION Developing Modular Syntheses of Diverse Nitrogen Heterocycle-Based Compounds for Metal Complexes, Catalysis, and Therapeutics by Michael David Elliott Sterling Doctor of Philosophy, Graduate Program in Chemistry University of California, Riverside, March 2019 Dr. Catharine H. Larsen, Chairperson The Larsen group develops new methods to synthesize nitrogen- containing molecules, focusing on accessing hindered and aromatic amines using green catalyst systems to convert inexpensive starting materials directly to high-value products. Amines and heteroaromatic compounds permeate the list of top-grossing pharmaceuticals. Developing novel methodologies for the formation of these drug-like molecules streamlines the discovery of treatments for cancer, HIV, malaria, and other maladies, while decreasing environmental impact. In addition to purely organic therapeutics, metal-based treatments to effectively treat ailments, and there continues to be special interest in their ligands, the organic molecules which enable metallic drug delivery. To this end, we have developed solvent- and chromatography-free, catalytic methods that provide a wide range of 2-(2’-pyridyl)quinolines, 2-(2’-pyridyl)triazoles, and 2-(2’- pyridyl)pyrazoles, heteroaromatic ligands that also offer their own intrinsic bioactivity. vii Our modular methods provide these heteroaromatic compounds with a variety of substituents simply by selecting the appropriate starting materials. Due to the facile construction of an electronically-diverse library, a series of each type of 2-(2’-pyridyl)quinoline (PyQuin), 2-(2’-pyridyl)triazole (PyTri), and 2-(2’- pyridyl)pyrazole (PyPyr) ligands were complexed to different transition metals, including gold, copper, palladium, and platinum. The effect of the ligands’ substituents on the metal complex were tracked by proton NMR spectroscopy and X-ray crystal structure analysis. Ready access to mixed LX-type PyPyr ligands resulted in the discovery of a thoroughly unique 5-coordinate, square- based pyramidal copper(II) complex. Catalytic activity was observed with both palladium(II) and gold(III) complexes of the PyTri ligands. In culmination, PyTri- gold(III) complexes were found to be essential for formation of an unprecedented 1,4-dihydroquinoline product from the hydroamination reaction of aniline and phenylacetylene. viii Table of Contents Acknowledgements……………………………………………………………………..v Abstract………………………………………………………………………………….vi List of Schemes ………………………………………………………………………..xi List of Tables…………………………………………………………………………..xvi List of Figures…………………………………………………………………………xvii Chapter One: Nitrogen Containing Small Molecules and Heterocycles 1.1 Introduction………………………………………………………………………….1 1.2 Heterocycles ………………………………………………………………………..1 1.3 Small Molecules and their Role in Therapeutics………………………………..2 1.4 Lipinski’s Rule of Five………………………………………………………………4 1.5 Examples of Nitrogen Heterocycle-Containing Small Molecule Therapeutics.5 1.6 Heterocycles as Ligands for Metal Complexes………………………………….8 1.7 References…………………………………………………………………………..9 Chapter Two: Modular Syntheses of Highly Substituted Quinolines and the Development of 4-phenyl-2-(2ʹ-pyridyl)quinolines (PyQuins) 2.1 Introduction………………………………………………………………………...12 2.2 Precedential Methods for the Synthesis of Quinolines………………………..12 2.3 Green Synthesis of 2,4-substituted Quinolines via 3-Component Coupling..19 2.4 Synthesis of 4-phenyl-2-(2ʹ-pyridyl)quinolines (PyQuins)…………………….21 2.5 Alternative Syntheses of PyQuins……………………………………………….28 ix 2.6 Eli Lilly Open Innovation Drug Discovery: Bioactivity of PyQuins……………33 2.7 References…………………………………………………………………………41 2.8 Supporting Information…………………………………………………………...44 Chapter 3: Synthesis of Novel Gold (III) Complexes with PyQuin Ligands 3.1 Introduction……………………………………………………………………….114 3.2 Gold (III) Complexes as Catalysts……………………………………………..118 3.3 Gold (III) Complexes with Bidentate Ligands Precedent…………………….120 + 3.4 Synthesis of R-PyQuin(AuCl3) and R-PyQuin(AuCl2) Complexes………...122 3.5 NMR Characterization and Comparison of Complexes……………………..127 3.6 X-Ray Crystallographic Confirmation of Complexes…………………………129 3.7 References……………………………………………………………………….135 3.8 Supporting Information………………………………………………………….137 Chapter Four: Investigation of the Solution-Phase Behavior for PyQuin Gold (III) Complexes and Observance of Gold Nanoparticles 4.1 Introduction………………………………………………………………………190 4.2 Ligand Exchange
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