Chemistry is traditionally divided into organic and inorganic chemistry. Safety of Isoxazole, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent，Which mentioned a new discovery about 288-14-2
This study reports an efficient four-step method to synthesize a series of new (4S,8aS)-3,4-diphenyl-6,7,8,8a-tetrahydro-4H-isoxazolo[3,4-a]pyrrolizines. The first step involves a copper(II) acetylacetonate catalyzed three component coupling of aldehyde, (S)-pyrrolidin-2-ylmethanol, and alkynes (A3 coupling) to form propargylamines (4 a?4 n). The coupling reaction is applicable to various aldehydes, amines, and alkynes and provides the propargylamines in good to excellent yields with excellent distereoselectivities. Products (4 a?4 n) were converted into aldehydes (5 a?5 n) by Swern oxidation, aldehydes (5 a?5 n) were reacted with hydroxyl amine hydrochloride to form aldoxime (6 a?6 n), respectively. Further aldoximes (6 a?6 n) underwent an intramolecular 1,3-dipolar cycloaddition to form tricyclic-fused isoxazoles (7 a?7 n). The 1,3-dipolar cycloaddition reaction tolerates high structural diversity and generated desired products (7 a?7 n) in moderate to good yields and excellent diastereoselectivities. A proposed mechanism for synthesis of 7 a is reported.
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Reference：
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem