| Autor: |
Kento Iwai, Akari Hikasa, Kotaro Yoshioka, Shinki Tani, Kazuto Umezu, Nagatoshi Nishiwaki |
| Jazyk: |
angličtina |
| Rok vydání: |
2024 |
| Předmět: |
|
| Zdroj: |
Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 2827-2833 (2024) |
| Druh dokumentu: |
article |
| ISSN: |
1860-5397 |
| DOI: |
10.3762/bjoc.20.238 |
| Popis: |
The N,O-acetal derived from diethyl mesoxalate (DEMO) undergoes elimination of acetic acid upon treatment with a base, leading to the formation of N-acylimine in situ. Lithium acetylide readily attacks the imino group to afford N,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. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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