Flow reaction system for the synthesis of benzoylacetonitrile via the reaction of amides and acetonitrile

Joonyoung Kim; Myeong Seong Park; Sunwoo Lee; Kwang Ho Song

doi:10.1016/j.tetlet.2022.154201

Flow reaction system for the synthesis of benzoylacetonitrile via the reaction of amides and acetonitrile

Joonyoung Kim, Myeong Seong Park, Sunwoo Lee, Kwang Ho Song

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Unactivated amides, such as N,N-dimethylbenzamide, react with acetonitrile in the presence of LiHMDS under flow reaction conditions to afford corresponding benzoylacetonitriles in good yields. The sequential flow reaction system is also applicable to the synthesis of benzoylacetonitrile from N-methylbenzamide.

Original language	English
Article number	154201
Journal	Tetrahedron Letters
Volume	111
DOIs	https://doi.org/10.1016/j.tetlet.2022.154201
Publication status	Published - 2022 Nov 23

Bibliographical note

Funding Information:
This research was supported by the grant funded by the Korean government ( MSIT ) ( NRF-2021R1A2C1005169 ) and the Korea University . Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center.

Funding Information:
This research was supported by the grant funded by the Korean government (MSIT) (NRF-2021R1A2C1005169) and the Korea University. Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center.

Publisher Copyright:
© 2022 Elsevier Ltd

Keywords

Amide
Benzoylacetonitrile
C-N bond activation
Flow reaction
LiHMDS

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2022.154201

Cite this

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title = "Flow reaction system for the synthesis of benzoylacetonitrile via the reaction of amides and acetonitrile",

abstract = "Unactivated amides, such as N,N-dimethylbenzamide, react with acetonitrile in the presence of LiHMDS under flow reaction conditions to afford corresponding benzoylacetonitriles in good yields. The sequential flow reaction system is also applicable to the synthesis of benzoylacetonitrile from N-methylbenzamide.",

keywords = "Amide, Benzoylacetonitrile, C-N bond activation, Flow reaction, LiHMDS",

author = "Joonyoung Kim and Park, {Myeong Seong} and Sunwoo Lee and Song, {Kwang Ho}",

note = "Funding Information: This research was supported by the grant funded by the Korean government ( MSIT ) ( NRF-2021R1A2C1005169 ) and the Korea University . Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center. Funding Information: This research was supported by the grant funded by the Korean government (MSIT) (NRF-2021R1A2C1005169) and the Korea University. Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center. Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

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doi = "10.1016/j.tetlet.2022.154201",

language = "English",

volume = "111",

journal = "Tetrahedron Letters",

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T1 - Flow reaction system for the synthesis of benzoylacetonitrile via the reaction of amides and acetonitrile

AU - Kim, Joonyoung

AU - Park, Myeong Seong

AU - Lee, Sunwoo

AU - Song, Kwang Ho

N1 - Funding Information: This research was supported by the grant funded by the Korean government ( MSIT ) ( NRF-2021R1A2C1005169 ) and the Korea University . Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center. Funding Information: This research was supported by the grant funded by the Korean government (MSIT) (NRF-2021R1A2C1005169) and the Korea University. Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center. Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/11/23

Y1 - 2022/11/23

N2 - Unactivated amides, such as N,N-dimethylbenzamide, react with acetonitrile in the presence of LiHMDS under flow reaction conditions to afford corresponding benzoylacetonitriles in good yields. The sequential flow reaction system is also applicable to the synthesis of benzoylacetonitrile from N-methylbenzamide.

AB - Unactivated amides, such as N,N-dimethylbenzamide, react with acetonitrile in the presence of LiHMDS under flow reaction conditions to afford corresponding benzoylacetonitriles in good yields. The sequential flow reaction system is also applicable to the synthesis of benzoylacetonitrile from N-methylbenzamide.

KW - Amide

KW - Benzoylacetonitrile

KW - C-N bond activation

KW - Flow reaction

KW - LiHMDS

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U2 - 10.1016/j.tetlet.2022.154201

DO - 10.1016/j.tetlet.2022.154201

M3 - Article

AN - SCOPUS:85140300545

SN - 0040-4039

VL - 111

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154201

ER -

Flow reaction system for the synthesis of benzoylacetonitrile via the reaction of amides and acetonitrile

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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