Synthesis of α‑Methylene-β-Lactams via PPh3‑Catalyzed Umpolung Cyclization of Propiolamides

Synthesis of α‑Methylene-β-Lactams via PPh3‑Catalyzed Umpolung Cyclization of Propiolamides

We report herein a facile synthesis of α-methylene-β-lactams. Thus, under the catalysis of triphenylphosphine, a number of 2-propiolamidoacetates or α-propiolamido ketones in refluxing ethanol underwent umpolung cyclization to afford the corresponding 4-substituted 3-methylene­azetidin-2-ones in hig...

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Veröffentlicht in:Journal of organic chemistry 2015-01, Vol.80 (1), p.628-633
Hauptverfasser: Zhu, Lin, Xiong, Yan, Li, Chaozhong
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Catalysis
Cyclization
Cyclopropanes - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Molecular Structure
Phosphines - chemistry
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Zusammenfassung:We report herein a facile synthesis of α-methylene-β-lactams. Thus, under the catalysis of triphenylphosphine, a number of 2-propiolamidoacetates or α-propiolamido ketones in refluxing ethanol underwent umpolung cyclization to afford the corresponding 4-substituted 3-methylene­azetidin-2-ones in high yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502265a