4.5 Article

Tin-Powder-Promoted One-Pot Synthesis of 5-Trifluoromethyl-5-aryl-3-methylidenepyrrolidin-2-ones

Journal

SYNTHESIS-STUTTGART
Volume 50, Issue 9, Pages 1907-1913

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1591909

Keywords

lactams; allylation; tin; trifluoromethyl ketones; acylhydrazines

Funding

  1. National Natural Science Foundation of China [21462037, 21662030]
  2. Key Laboratory Polymer Materials of Gansu Province (Northwest Normal University)
  3. Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, China
  4. State Key Laboratory of Applied Organic Chemistry, Lanzhou University

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A simple and efficient synthetic approach is reported for the synthesis of 5-trifluoromethyl-5-aryl-3-methylidenepyrrolidin-2-ones in moderate to excellent yields via an acid-catalyzed one-pot multicomponent reaction of aromatic trifluoromethyl ketones, acylhydrazines, and ethyl 2-(bromomethyl)acrylate promoted by tin powder. The protocol is operationally simple. The overall process involves allylation and cyclization of the intermediate of acylhydrazones.

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