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Generation of nitrite oxides via O-tributylstannyl aldoximes; application to the synthesis of isoxazolines and isoxazoles

1994; Issue: 4 Linguagem: Inglês

10.1039/p19940000413

2050-8255

Osamu Moriya, Hideo Takenaka, M. Iyoda, Yoshikiyo Urata, Takeshi Endo,

Synthesis and Biological Evaluation

Nitrite oxides were generated readily by the reaction of aldoximes 1, with tert-butyl hypochlorite and bis(tributyltin) oxide. The reaction proceeded efficiently under mild conditions, in which O-stannylated aldoximes 2 are thought to be key intermediates. This reaction system was applicable to the one-pot syntheses of isoxazole derivatives 4 and 5 in the presence of dipolarophiles via a [3 + 2] cycloaddition.