1,3-Diketone-Mediated Synthesis of Symmetrical Aryl Imides from Activated Amides

Myeong Seong Park; Karthik Rajan Rajamanickam; Kwang Ho Song; Sunwoo Lee

doi:10.1002/ajoc.202300469

1,3-Diketone-Mediated Synthesis of Symmetrical Aryl Imides from Activated Amides

Myeong Seong Park, Karthik Rajan Rajamanickam, Kwang Ho Song^*, Sunwoo Lee^*

^*Corresponding author for this work

Department of Chemical and Biological Engineering

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

4 Citations (Scopus)

Abstract

Symmetrical aryl imides are synthesized from the reaction of activated amides such as N-phenyl-N-tosyl benzamides. The amine source is provided by lithium hexamethyldisilazide (LiHMDS), and a 1,3-diketone mediates the generation of the N-acyl donor from N,N-bis(trimethylsilyl)amide. Various symmetrical aryl amides are thus formed in moderate to good yields.

Original language	English
Article number	e202300469
Journal	Asian Journal of Organic Chemistry
Volume	12
Issue number	12
DOIs	https://doi.org/10.1002/ajoc.202300469
Publication status	Published - 2023 Dec

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

1,3-diketone
amide
imide
lithium hexamethyldisilane
transamidation

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.202300469

Cite this

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title = "1,3-Diketone-Mediated Synthesis of Symmetrical Aryl Imides from Activated Amides",

abstract = "Symmetrical aryl imides are synthesized from the reaction of activated amides such as N-phenyl-N-tosyl benzamides. The amine source is provided by lithium hexamethyldisilazide (LiHMDS), and a 1,3-diketone mediates the generation of the N-acyl donor from N,N-bis(trimethylsilyl)amide. Various symmetrical aryl amides are thus formed in moderate to good yields.",

keywords = "1,3-diketone, amide, imide, lithium hexamethyldisilane, transamidation",

author = "Park, \{Myeong Seong\} and Rajamanickam, \{Karthik Rajan\} and Song, \{Kwang Ho\} and Sunwoo Lee",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = dec,

doi = "10.1002/ajoc.202300469",

language = "English",

volume = "12",

journal = "Asian Journal of Organic Chemistry",

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T1 - 1,3-Diketone-Mediated Synthesis of Symmetrical Aryl Imides from Activated Amides

AU - Park, Myeong Seong

AU - Rajamanickam, Karthik Rajan

AU - Song, Kwang Ho

AU - Lee, Sunwoo

PY - 2023/12

Y1 - 2023/12

N2 - Symmetrical aryl imides are synthesized from the reaction of activated amides such as N-phenyl-N-tosyl benzamides. The amine source is provided by lithium hexamethyldisilazide (LiHMDS), and a 1,3-diketone mediates the generation of the N-acyl donor from N,N-bis(trimethylsilyl)amide. Various symmetrical aryl amides are thus formed in moderate to good yields.

AB - Symmetrical aryl imides are synthesized from the reaction of activated amides such as N-phenyl-N-tosyl benzamides. The amine source is provided by lithium hexamethyldisilazide (LiHMDS), and a 1,3-diketone mediates the generation of the N-acyl donor from N,N-bis(trimethylsilyl)amide. Various symmetrical aryl amides are thus formed in moderate to good yields.

KW - 1,3-diketone

KW - amide

KW - imide

KW - lithium hexamethyldisilane

KW - transamidation

UR - https://www.scopus.com/pages/publications/85174838015

U2 - 10.1002/ajoc.202300469

DO - 10.1002/ajoc.202300469

M3 - Article

AN - SCOPUS:85174838015

SN - 2193-5807

VL - 12

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 12

M1 - e202300469

ER -

1,3-Diketone-Mediated Synthesis of Symmetrical Aryl Imides from Activated Amides

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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