Theses and Dissertations at Montana State University (MSU)
Permanent URI for this collectionhttps://scholarworks.montana.edu/handle/1/733
Browse
6 results
Search Results
Item The expansion and optimization of ZN(II)-mediated intramolecular metalloamination and subsequent CU(I)-catalyzed functionalization for the construction of pyrrolidines and piperidines(Montana State University - Bozeman, College of Letters & Science, 2023) Frabitore, Christian Ames; Chairperson, Graduate Committee: Thomas S. Livinghouse; This is a manuscript style paper that includes co-authored chapters.Nitrogen-containing heterocycles (azacycles) are ubiquitous in pharmaceutical agents. Their ability to moderate and modulate the activity of drugs in the body make them especially powerful, and thus sought after, synthetic targets. While the synthesis of many popular azacycles has been greatly improved in recent years, the production of pyrrolidines and piperidines has not received as much attention despite their standing as the 1st and 5th most common azacycles in FDA-approved drugs. The intramolecular Zn(II)-mediated metalloamination/cyclization of N,Ndimethylhydrazinoalkenes provides structurally diverse pyrrolidines and piperidines with the added advantage of a subsequent functionalization step, efficiently building molecular complexity in one reaction sequence. Herein, this method is optimized and improved by the addition of a new hydrazone reduction method, the inclusion of 1-bromoalkynes in the functionalization step, and multiple key discoveries in the reagents used to effect these transformations. Furthermore, preliminary results adding N,N-dimethylhydrazinoallenes as substrates for this powerful method are presented.Item Effects of heteroatoms in heterocyclic molecules(Montana State University - Bozeman, College of Letters & Science, 1972) Sun, Kauo-rongItem Heteroatom influences on structure and reactivity(Montana State University - Bozeman, College of Letters & Science, 1978) Theodore, John JamesItem Theoretical and experimental nonaromatic heterocyclic chemistry(Montana State University - Bozeman, College of Letters & Science, 1975) Lipkowitz, Kenneth BarryItem Heterocyclic chemistry : unique role of heteroatoms in structure and reactivity(Montana State University - Bozeman, College of Letters & Science, 1991) Lee, ChangjooItem New synthetic methodologies for natural products(Montana State University - Bozeman, College of Letters & Science, 1978) Bornmann, William Gerard