We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition.
- Authors
Hoffman, Gavin R.; Schoffstall, Allen M.
- Abstract
Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an N-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing "6-5-5-5"-membered ring fusions. The initial condensation was achieved through reaction of o-phenylenediamine with ethyl diethoxyacetate, followed by alkylation with propargyl bromide, deprotection of the acetal to the aldehyde, formation of an aldoxime, and intramolecular nitrile oxide cycloaddition (INOC). Characterization of the aldoxime and tetracyclic isoxazole is included herein.
- Subjects
NITRILE oxides; RING formation (Chemistry); PROPARGYL bromide; ALKYLATION; CLICK chemistry
- Publication
Molbank, 2024, Vol 2024, Issue 1, pM1767
- ISSN
1422-8599
- Publication type
Article
- DOI
10.3390/M1767