Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System

Katsuhiro Komuro, Aiichiro Nagaki, Hiroki Shimoda, Masahiro Uwamori, Jun Ichi Yoshida, Masahisa Nakada

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Successful transformations of 3-iodo-1-methyl-5,6-dihydropyridin-2(1 H)-one into its derivatives by a halogen-lithium exchange and subsequent reactions in a flow microreactor system are described. The methylation of the organolithium compound generated from 3-iodo-1-methyl-5,6-dihydropyridin-2(1 H)-one in the flow microreactor system afforded the desired methylated product in 68% yield, whereas the yield of the corresponding batch reaction was 23%. This superiority of the flow microreactor system was further emphasized in the reaction of the organolithium compound with methoxycarbonyl isocyanate, which gave the desired imide in 78% yield by using the flow microreactor system whereas the yield of the corresponding batch reaction was only 2%. The established flow microreactor system was also effectively used for the reaction of the organolithium compound with phenyl isocyanate to afford the desired product in 52% yield.

Original languageEnglish
Article numberst-2018-u0401-l
Pages (from-to)1989-1994
Number of pages6
JournalSynlett
Volume29
Issue number15
DOIs
Publication statusPublished - 2018 Jan 1

Keywords

  • flow microreactor system
  • halogen-lithium exchange reaction
  • imides
  • isocyanates
  • lithiation
  • methylation

ASJC Scopus subject areas

  • Organic Chemistry

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    Komuro, K., Nagaki, A., Shimoda, H., Uwamori, M., Yoshida, J. I., & Nakada, M. (2018). Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System. Synlett, 29(15), 1989-1994. [st-2018-u0401-l]. https://doi.org/10.1055/s-0037-1610228