Gulten, Sirin2025-01-272025-01-2720200021-95841938-1328https://doi.org/10.1021/acs.jchemed.9b01169https://hdl.handle.net/20.500.12428/24751The advanced organic chemistry experiments describe the preparation of fused six-membered lactams to isoxazole and isoxazoline by employing Ugi four-component reaction (U-4CR) and intramolecular nitrile oxide cyclization (INOC) synthetic sequence. The experiments were carried out in 28 h (overnight for U-4CR) and 2 h (for INOC) using commercially available starting materials. The two-step reaction involves the in situ imine formation in the one-pot multicomponent reaction and in situ nitrile oxide formation in the INOC. The experiments are useful in the organic chemistry curriculum for the introduction of a onepot multicomponent reaction and 1,3-dipolar cycloaddition reactions.eninfo:eu-repo/semantics/closedAccessUpper-Divison UndergraduateLaboratory InstructionOrganic ChemistryHands-On Learning/ManipulativesSynthesisInquiry-Based/Discovery LearningAmidesHeterocyclesNMR SpectroscopyDiastereomersArticle97103839384610.1021/acs.jchemed.9b01169Q2WOS:0005809539000502-s2.0-85091918353Q1