Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates
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...
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Beilstein-Institut
2024-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.238 |
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| author | Kento Iwai Akari Hikasa Kotaro Yoshioka Shinki Tani Kazuto Umezu Nagatoshi Nishiwaki |
| author_facet | Kento Iwai Akari Hikasa Kotaro Yoshioka Shinki Tani Kazuto Umezu Nagatoshi Nishiwaki |
| author_sort | Kento Iwai |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-bb5f11a54a764fffb90fe1c0a1ec65f3 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-bb5f11a54a764fffb90fe1c0a1ec65f32024-12-02T08:46:11ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-11-012012827283310.3762/bjoc.20.2381860-5397-20-238Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylatesKento Iwai0Akari Hikasa1Kotaro Yoshioka2Shinki Tani3Kazuto Umezu4Nagatoshi Nishiwaki5School of Engineering Science, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan School of Engineering Science, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan Kumiai Chemical Industry Co. Ltd., Nakanogo, Fuji, Shizuoka 421-3306, Japan and 5K • I Chemical Industry Co. Ltd., Shinoshinden, Iwata, Shizuoka 437-1213, Japan Kumiai Chemical Industry Co. Ltd., Nakanogo, Fuji, Shizuoka 421-3306, Japan and 5K • I Chemical Industry Co. Ltd., Shinoshinden, Iwata, Shizuoka 437-1213, Japan Kumiai Chemical Industry Co. Ltd., Nakanogo, Fuji, Shizuoka 421-3306, Japan and 5K • I Chemical Industry Co. Ltd., Shinoshinden, Iwata, Shizuoka 437-1213, Japan School of Engineering Science, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan 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.https://doi.org/10.3762/bjoc.20.238acid amidediethyl mesoxalaten-acylamineoxazolepropargylamine |
| spellingShingle | Kento Iwai Akari Hikasa Kotaro Yoshioka Shinki Tani Kazuto Umezu Nagatoshi Nishiwaki Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates Beilstein Journal of Organic Chemistry acid amide diethyl mesoxalate n-acylamine oxazole propargylamine |
| title | Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates |
| title_full | Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates |
| title_fullStr | Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates |
| title_full_unstemmed | Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates |
| title_short | Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates |
| title_sort | synthesis of tricarbonylated propargylamine and conversion to 2 5 disubstituted oxazole 4 carboxylates |
| topic | acid amide diethyl mesoxalate n-acylamine oxazole propargylamine |
| url | https://doi.org/10.3762/bjoc.20.238 |
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