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

Aoyama Tadashi; Itoh Ken Ichi; Furukawa Yuri; Hayakawa Mamiko; Shimada Shigeru; Ouchi Akihiko

doi:10.1055/s-0036-1588914

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

作者：Aoyama Tadashi; Itoh Ken Ichi; Furukawa Yuri; Hayakawa Mamiko; Shimada Shigeru; Ouchi Akihiko

来源：Synlett, 2017, 28(4): 489-493.

DOI：10.1055/s-0036-1588914

摘要

A novel method was developed for the synthesis of N-alkoxy-acylimidoyl halide by the reaction of alpha-nitro ketone and alkyl halides in the presence of NaHSO4/SiO2. Nitrile oxides that are generated from alpha-nitro 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.