{"id":{"repo_id":"central-wash","oai_identifier":"oai:digitalcommons.cwu.edu:etd-1755"},"canonical_url":"https://search.dev.ndltd.org/etd/central-wash/oai:digitalcommons.cwu.edu:etd-1755","repository":{"repo_id":"central-wash","name":"Central Washington University","base_url":"https://digitalcommons.cwu.edu/do/oai/"},"display":{"title":"A Diversity-Oriented Synthesis Approach to Functionalized Azaheterocycles using Cyclic Alpha-Halo Eneformamides","abstract":"Functionalized piperidines, azepanes, azamacrocycles, morpholines, and thiomorpholines are common structural motifs found in a wide range of pharmaceuticals such as carmegliptine, levofloxacin, thioridazine, claviciptic acid, and azithomycin. As a result, there is a strong desire to construct highly functionalized nitrogen-bearing ring scaffolds in order to construct a wide range of drug possibilities. There are several non-modular and step-uneconomical synthetic methods used in the construction of these aforementioned motifs such as ring closing metathesis, ring expansions, and intramolecular reductive amination. In this research, we present a step-economical, cost-effective, scalable, and diversity-oriented synthesis approach to highly functionalized N-heterocycles through the intermediacy of α-halo enamines/enamides. The synthetic utility of the method is exemplified through the construction of quaternary cyclic propargylic and homoallylic amines, polycyclic lactams, as well as chiral dihydro 1,4-oxazines and thiazines. Given the generality of the approach, we are confident that the synthesis and medicinal chemistry communities will undoubtedly embrace it, thus, endowing it with a practical advantage over existing methodologies.","abstract_html":"Functionalized piperidines, azepanes, azamacrocycles, morpholines, and thiomorpholines are common structural motifs found in a wide range of pharmaceuticals such as carmegliptine, levofloxacin, thioridazine, claviciptic acid, and azithomycin. As a result, there is a strong desire to construct highly functionalized nitrogen-bearing ring scaffolds in order to construct a wide range of drug possibilities. There are several non-modular and step-uneconomical synthetic methods used in the construction of these aforementioned motifs such as ring closing metathesis, ring expansions, and intramolecular reductive amination. In this research, we present a step-economical, cost-effective, scalable, and diversity-oriented synthesis approach to highly functionalized N-heterocycles through the intermediacy of α-halo enamines/enamides. The synthetic utility of the method is exemplified through the construction of quaternary cyclic propargylic and homoallylic amines, polycyclic lactams, as well as chiral dihydro 1,4-oxazines and thiazines. Given the generality of the approach, we are confident that the synthesis and medicinal chemistry communities will undoubtedly embrace it, thus, endowing it with a practical advantage over existing methodologies.","abstract_has_math":false,"creators":["Langevin, Spencer A."],"institution":null,"degree_name":"Master of Science (MS)","degree_level":null,"degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Timothy K. Beng","Levente Fabry-Asztalos","Gil Belofsky"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2017,"date_issued":"2017-01-01T08:00:00Z","date_published":"2017-01-01T08:00:00Z","updated_at":"2026-07-24T01:37:09Z","subjects":["Diversity Oriented","Eneformamides","Azaheterocycles","Nitrogen-bearing","polycycles","macrocycles","Heterocyclic Compounds","Macromolecular Substances","Medicinal and Pharmaceutical Chemistry","Organic Chemicals","Organic Chemistry","Other Chemicals and Drugs","Pharmaceutical Preparations","Pharmaceutics and Drug Design","Polycyclic Compounds"],"languages":["English"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://digitalcommons.cwu.edu/etd/779","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Timothy K. 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As a result, there is a strong desire to construct highly functionalized nitrogen-bearing ring scaffolds in order to construct a wide range of drug possibilities. There are several non-modular and step-uneconomical synthetic methods used in the construction of these aforementioned motifs such as ring closing metathesis, ring expansions, and intramolecular reductive amination. In this research, we present a step-economical, cost-effective, scalable, and diversity-oriented synthesis approach to highly functionalized N-heterocycles through the intermediacy of α-halo enamines/enamides. The synthetic utility of the method is exemplified through the construction of quaternary cyclic propargylic and homoallylic amines, polycyclic lactams, as well as chiral dihydro 1,4-oxazines and thiazines. Given the generality of the approach, we are confident that the synthesis and medicinal chemistry communities will undoubtedly embrace it, thus, endowing it with a practical advantage over existing methodologies."]},{"key":"dc:title","label":"Title","values":["A Diversity-Oriented Synthesis Approach to Functionalized Azaheterocycles using Cyclic Alpha-Halo Eneformamides"]}]}],"canonical_facts":{"dc:contributor":["Timothy K. Beng","Levente Fabry-Asztalos","Gil Belofsky"],"dc:creator":["Langevin, Spencer A."],"dc:date.available":["2019-09-25T07:00:00Z"],"dc:description.abstract":["Functionalized piperidines, azepanes, azamacrocycles, morpholines, and thiomorpholines are common structural motifs found in a wide range of pharmaceuticals such as carmegliptine, levofloxacin, thioridazine, claviciptic acid, and azithomycin. As a result, there is a strong desire to construct highly functionalized nitrogen-bearing ring scaffolds in order to construct a wide range of drug possibilities. There are several non-modular and step-uneconomical synthetic methods used in the construction of these aforementioned motifs such as ring closing metathesis, ring expansions, and intramolecular reductive amination. In this research, we present a step-economical, cost-effective, scalable, and diversity-oriented synthesis approach to highly functionalized N-heterocycles through the intermediacy of α-halo enamines/enamides. The synthetic utility of the method is exemplified through the construction of quaternary cyclic propargylic and homoallylic amines, polycyclic lactams, as well as chiral dihydro 1,4-oxazines and thiazines. Given the generality of the approach, we are confident that the synthesis and medicinal chemistry communities will undoubtedly embrace it, thus, endowing it with a practical advantage over existing methodologies."],"dc:identifier":["https://digitalcommons.cwu.edu/etd/779"],"dc:language":["English"],"dc:subject":["Diversity Oriented","Eneformamides","Azaheterocycles","Nitrogen-bearing","polycycles","macrocycles","Heterocyclic Compounds","Macromolecular Substances","Medicinal and Pharmaceutical Chemistry","Organic Chemicals","Organic Chemistry","Other Chemicals and Drugs","Pharmaceutical Preparations","Pharmaceutics and Drug Design","Polycyclic Compounds"],"dc:title":["A Diversity-Oriented Synthesis Approach to Functionalized Azaheterocycles using Cyclic Alpha-Halo Eneformamides"],"dc:type":["Text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_name":["Master of Science (MS)"]},"updated_at":"2026-07-24T01:37:09Z"}