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 language | English |
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Article number | st-2018-u0401-l |
Pages (from-to) | 1989-1994 |
Number of pages | 6 |
Journal | Synlett |
Volume | 29 |
Issue number | 15 |
DOIs | |
Publication status | Published - 2018 |
Keywords
- flow microreactor system
- halogen-lithium exchange reaction
- imides
- isocyanates
- lithiation
- methylation
ASJC Scopus subject areas
- Organic Chemistry