1385020-48-3Relevant academic research and scientific papers
Synthesis of 4-amino-1,2,3,4-tetrahydropyridine derivatives by intramolecular nucleophilic addition of tertiary enamides to in-situ generated imines
Tong, Shuo,Yang, Xu,Wang, De-Xian,Zhao, Liang,Zhu, Jieping,Wang, Mei-Xiang
, p. 6492 - 6497 (2012)
The reactivity of stable tertiary enamides in nucleophilic addition reaction with various in-situ generated imines was explored. Under very mild conditions, formyl-bearing tertiary enamides reacted with both aromatic and aliphatic amines to form imine intermediates. In the absence or presence of p-toluenesulfonic acid as a catalyst, intramolecular nucleophilic addition of enamide to imine functionality proceeded effectively to produce diverse 4-amino-1,2,3,4-tetrahydropyridine derivatives in good to excellent yields.
Exploring tertiary enamides as versatile synthons in organic synthesis
Wang, Mei-Xiang
, p. 6039 - 6049 (2015/04/14)
Tertiary enamides have long been thought of as stable and marginally valuable enamine variants in synthesis. This notion has been challenged, however, in recent years. Enabling the regulation of the cross-conjugation system of the tertiary enamides has been successfully shown to enhance delocalization of the nitrogen lone-pair electrons into a carbon-carbon double, thereby reinvigorating the enaminic reactivity of the tertiary enamides. In this article, I summarize the recent advances in the exploration of the nucleophilic reactions of tertiary enamides and their applications in the synthesis of natural products and heterocyclic compounds of biological and pharmaceutical relevance, with a primary focus on our own work.
