锡粉促进由醛或酮、酰肼和2-(溴甲基)丙烯酸酯一锅法构建α-亚甲基-γ-内酰胺和螺内酰胺

Tin Powder-Promoted One-Pot Construction of α-Methylene-γ-lactams and Spirolactams from Aldehydes or Ketones, Acylhydrazines, and 2-(Bromomethyl)acrylate.

作者信息

Xu Yanli, Huang Danfeng, Wang Ke-Hu, Ma Junyan, Su Yingpeng, Fu Ying, Hu Yulai

机构信息

College of Chemistry and Chemical Engineering, Northwest Normal University , 967 Anning East Road, Lanzhou 730070, P. R. China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.

出版信息

J Org Chem. 2015 Dec 18;80(24):12224-33. doi: 10.1021/acs.joc.5b02154. Epub 2015 Nov 30.

DOI:10.1021/acs.joc.5b02154

PMID:26577682

Abstract

A concise and efficient method for the synthesis of α-methylene-γ-lactams is developed from multicomponent one-pot reactions of aldehydes or ketones, hydrazides, and ethyl 2-(bromomethyl)acrylate promoted by tin powder. The reaction proceeds smoothly under mild reaction conditions without using any catalyst to give the corresponding products in high yields. α-Methylene-γ-spirolactams can also be prepared from cyclic ketones.

摘要

开发了一种简洁高效的合成α-亚甲基-γ-内酰胺的方法，该方法以醛或酮、酰肼和2-(溴甲基)丙烯酸乙酯为原料，在锡粉促进下通过多组分一锅法反应实现。该反应在温和的反应条件下顺利进行，无需使用任何催化剂，即可高产率地得到相应产物。α-亚甲基-γ-螺内酰胺也可由环酮制备。