23350-02-9Relevant articles and documents
Synthesis of 4-amino-5-allenylisoxazolesviagold(i)-catalysed propargyl aza-Claisen rearrangement
Tsuda, Masato,Morita, Taiki,Fukuhara, Shintaro,Nakamura, Hiroyuki
supporting information, p. 1358 - 1364 (2021/02/27)
Propargyl aza-Claisen rearrangement of 4-propargylaminoisoxazoles1proceeded in the presence of cationic gold(i) catalysts to give 4-amino-5-allenylisoxazoles2in good to high yields. The silyl group at the terminal alkyne and a cationic gold(i) catalyst bearing a sterically bulky ligand are essential for the generation of isolable allene intermediates. TheN-protection of the generated 4-amino-5-allenylisoxazoles2allowed the isolation of 5-allenylisoxazoles4that have never been synthesized.N-Propargyl aniline5was successfully converted to the correspondingortho-allenyl aniline6under the current reaction conditions.