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 |
|---|---|
| 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 Jan 1 |
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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 journal › Article
}
TY - JOUR
T1 - Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System
AU - Komuro, Katsuhiro
AU - Nagaki, Aiichiro
AU - Shimoda, Hiroki
AU - Uwamori, Masahiro
AU - Yoshida, Jun Ichi
AU - Nakada, Masahisa
PY - 2018/1/1
Y1 - 2018/1/1
N2 - 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.
AB - 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.
KW - flow microreactor system
KW - halogen-lithium exchange reaction
KW - imides
KW - isocyanates
KW - lithiation
KW - methylation
UR - http://www.scopus.com/inward/record.url?scp=85053136337&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85053136337&partnerID=8YFLogxK
U2 - 10.1055/s-0037-1610228
DO - 10.1055/s-0037-1610228
M3 - Article
VL - 29
SP - 1989
EP - 1994
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 15
M1 - st-2018-u0401-l
ER -