439118-91-9Relevant academic research and scientific papers
The aza-ene or the Michael addition? Examination of an unusual substituent effect on the reaction of heterocyclic ketene aminals with ethyl propiolate
Zhao, Mei-Xin,Wang, Mei-Xiang,Huang, Zhi-Tang
, p. 1309 - 1316 (2007/10/03)
Heterocyclic ketene aminals having at least one secondary amino group underwent the aza-ene reaction with ethyl propiolate under various conditions to yield the corresponding adducts, which were readily transformed into the δ-lactam fused heterocyclic products with or without the aid of sodium ethoxide in refluxing ethanol, while the ester- and cyano-substituted tertiary enediamines acted as the strong Michael donor to add to ethyl propiolate in a polar or a protic solvent. The unusual substituent effect on the reactivity and mechanism was discussed.
