A Facile Synthesis of N-Alkoxyacylimidoyl Halides from α-Nitro Ketones and Alkyl Halides in the Presence of NaHSO4/SiO2

Abstract

A novel method was developed for the synthesis of N-alkoxyacylimidoyl halide by the reaction of α-nitro ketone and alkyl halides in the presence of NaHSO 4 /SiO 2 . Nitrile oxides that are generated from αnitro ketones by silica gel supported acid catalysts are the possible intermediate, which react with alkyl halides to form N-alkoxyacylimidoyl halides. Novel 17 N-alkoxyacylimidoyl halides were synthesized by this procedure.

A Facile Approach to the Synthesis of 3-Acylisoxazole Derivatives with Reusable Solid Acid Catalysts

“…From the results in the time course, it seems that the reaction rate of hydration is faster than cycloaddition because Amberlyst 15 directly react with 2l. Besides, even in the reaction using 1a and 2a, 2-octanone (8) was obtained via the hydration of 2a in 0.50 (reaction time: 1 h), 9.5 (2 h), 24 (4 h) and 26% (6 h) GLC yields, respectively. From the results, since the hydration of 2a by Amberlyst 15 is slower than 2l in the reaction rate, 3aa was formed in high yield in the reaction of 1a and 2a.…”