Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates

The , -acetal derived from diethyl mesoxalate (DEMO) undergoes elimination of acetic acid upon treatment with a base, leading to the formation of -acylimine in situ. Lithium acetylide readily attacks the imino group to afford ,1,1-tricarbonylated propargylamines. When the resulting propargylamine re...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2024-11, Vol.20 (1), p.2827-2833
Main Authors: Iwai, Kento, Hikasa, Akari, Yoshioka, Kotaro, Tani, Shinki, Umezu, Kazuto, Nishiwaki, Nagatoshi
Format: Article
Language:English
Subjects:
acid amide
Chemistry
diethyl mesoxalate
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n-acylamine
oxazole
propargylamine
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Summary:The , -acetal derived from diethyl mesoxalate (DEMO) undergoes elimination of acetic acid upon treatment with a base, leading to the formation of -acylimine in situ. Lithium acetylide readily attacks the imino group to afford ,1,1-tricarbonylated propargylamines. When the resulting propargylamine reacts with butyllithium, ring closure occurs between the ethynyl and carbamoyl groups, yielding 2,5-disubstituted oxazole-4-carboxylates. This cyclization also occurs when the propargylamine is heated with ammonium acetate, resulting in double activation.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.20.238