Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2001-2007.DOI: 10.6023/cjoc202010036 Previous Articles     Next Articles



彭福涛a, 黄立梁a, 黄军海b,*(), 冯煌迪a,*()   

  1. a 上海工程技术大学化学化工学院 上海 201620
    b 中国医药工业研究总院 上海医药工业研究院 上海 201203
  • 收稿日期:2020-10-28 修回日期:2020-12-30 发布日期:2021-02-07
  • 通讯作者: 黄军海, 冯煌迪
  • 基金资助:

Double aza-Morita-Baylis-Hillman Domino Reaction to Access Amino Derived 1,6-Dienes

Futao Penga, Liliang Huanga, Junhai Huangb,*(), Huangdi Fenga,*()   

  1. a College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
    b State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai 201203
  • Received:2020-10-28 Revised:2020-12-30 Published:2021-02-07
  • Contact: Junhai Huang, Huangdi Feng
  • About author:
    * Corresponding authors. E-mail: ;
  • Supported by:
    National Natural Science Foundation of China(31702070)

Aza-Morita-Baylis-Hillman reaction plays specific roles in the construction of C—C bond, and their applications in synthetic chemistry and pharmaceutical chemistry have also been well-documented. Herein, a novel 1,4-diazabicyclo- [2.2.2]octane (DABCO) mediated doubleaza-Morita-Baylis-Hillman cascade strategy toward synthetically important aza-MBH adducts is reported. Complementary to classical aza-MBH reaction, this protocol employs a wide variety of primary amines including benzyl, alkyl and aryl moieties as the reaction partners, giving an efficient alternative to produce amino derived 1,6-dienes in moderate to high yields in the presence of formaldehyde and α,β-unsaturated carbonyl compounds. Rather surprisingly, using an aqueous medium has proven to be successful in promoting the reaction efficiency and achieving a higher yield of target products. One-pot operation, high chemoselectivity, short reaction time, and broad substrate scope of primary amines exemplified the significant advances and practicability of this protocol.

Key words: aza-Morita-Baylis-Hillman reaction, domino reaction, primary amine, 1,6-diene