Arylethanolamines in Ritter reaction: Synthesis of 2,4‐Diarylimidazole Core

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Arylethanolamines in Ritter reaction: Synthesis of 2,4‐Diarylimidazole Core. / Smorodina, Anastasia A.; Buev, Evgeny M.; Moshkin, Vladimir S. и др.
в: Asian Journal of Organic Chemistry, Том 12, № 2, e202200656, 2023.

Результаты исследований: Вклад в журнал › Статья › Рецензирование

BibTeX

@article{982eb7c911e649fc88861912fb7c7ece,

title = "Arylethanolamines in Ritter reaction: Synthesis of 2,4‐Diarylimidazole Core",

abstract = "A three-step synthesis of imidazole core from arylethanolamines was achieved. A key to this sequence is a Ritter reaction of arylethanolamines promoted by perchloric acid, allowing the formation of 2-methylamino-1-(acylamino)-1-arylethanes in 33–82% yields. The latter were subjected to thermal cyclization into 4-arylimidazolines by simple heating in n-butanol in 51–95% yields or to one-pot cyclization-oxidation sequence to produce 2,4-diarylimidazoles in 73–93% yields. The efficiency of this approach was demonstrated on a straightforward one-pot synthesis of 2,4-diarylimidazoles from readily available starting materials: aromatic aldehydes, sarcosine, paraformaldehyde and benzonitriles, in 42–49% total yields. {\textcopyright} 2023 Wiley-VCH GmbH.",

author = "Smorodina, {Anastasia A.} and Buev, {Evgeny M.} and Moshkin, {Vladimir S.} and Sosnovskikh, {Vyacheslav Y.}",

note = "This work was financially supported by the Russian Science Foundation (Grant 22‐73‐10008).",

year = "2023",

doi = "10.1002/ajoc.202200656",

language = "English",

volume = "12",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "Wiley-VCH Verlag",

number = "2",

}

RIS

TY - JOUR

T1 - Arylethanolamines in Ritter reaction: Synthesis of 2,4‐Diarylimidazole Core

AU - Smorodina, Anastasia A.

AU - Buev, Evgeny M.

AU - Moshkin, Vladimir S.

AU - Sosnovskikh, Vyacheslav Y.

N1 - This work was financially supported by the Russian Science Foundation (Grant 22‐73‐10008).

PY - 2023

Y1 - 2023

N2 - A three-step synthesis of imidazole core from arylethanolamines was achieved. A key to this sequence is a Ritter reaction of arylethanolamines promoted by perchloric acid, allowing the formation of 2-methylamino-1-(acylamino)-1-arylethanes in 33–82% yields. The latter were subjected to thermal cyclization into 4-arylimidazolines by simple heating in n-butanol in 51–95% yields or to one-pot cyclization-oxidation sequence to produce 2,4-diarylimidazoles in 73–93% yields. The efficiency of this approach was demonstrated on a straightforward one-pot synthesis of 2,4-diarylimidazoles from readily available starting materials: aromatic aldehydes, sarcosine, paraformaldehyde and benzonitriles, in 42–49% total yields. © 2023 Wiley-VCH GmbH.

AB - A three-step synthesis of imidazole core from arylethanolamines was achieved. A key to this sequence is a Ritter reaction of arylethanolamines promoted by perchloric acid, allowing the formation of 2-methylamino-1-(acylamino)-1-arylethanes in 33–82% yields. The latter were subjected to thermal cyclization into 4-arylimidazolines by simple heating in n-butanol in 51–95% yields or to one-pot cyclization-oxidation sequence to produce 2,4-diarylimidazoles in 73–93% yields. The efficiency of this approach was demonstrated on a straightforward one-pot synthesis of 2,4-diarylimidazoles from readily available starting materials: aromatic aldehydes, sarcosine, paraformaldehyde and benzonitriles, in 42–49% total yields. © 2023 Wiley-VCH GmbH.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85146460746

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000913816800001

U2 - 10.1002/ajoc.202200656

DO - 10.1002/ajoc.202200656

M3 - Article

VL - 12

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

IS - 2

M1 - e202200656

ER -

ID: 35464559