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

1 Citation (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

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Imides
Isocyanates
Halogens
Methylation
Lithium
Derivatives
phenyl isocyanate

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System. / Komuro, Katsuhiro; Nagaki, Aiichiro; Shimoda, Hiroki; Uwamori, Masahiro; Yoshida, Jun Ichi; Nakada, Masahisa.

In: Synlett, Vol. 29, No. 15, st-2018-u0401-l, 01.01.2018, p. 1989-1994.

Research output: Contribution to journalArticle

Komuro, Katsuhiro ; Nagaki, Aiichiro ; Shimoda, Hiroki ; Uwamori, Masahiro ; Yoshida, Jun Ichi ; Nakada, Masahisa. / Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System. In: Synlett. 2018 ; Vol. 29, No. 15. pp. 1989-1994.
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