New three-component reaction: novel formation of a seven-membered ring by the unexpected reaction at the gamma-position of the beta-keto ester.
[reaction: see text] The novel three-component reaction of aromatic aldehydes, ethylenediamine, and beta-keto esters is described. In this reaction, beta-keto esters react at the gamma-position which is generally unreactive to produce the seven-membered ring compounds. Products have secondary amines and beta-enamino esters, which can serve in further functionalizations to produce molecular diversity.
Fujioka
Hiromichi
H
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan. fujioka@phs.osaka-u.ac.jp
Murai
Kenichi
K
Kubo
Ozora
O
Ohba
Yusuke
Y
Kita
Yasuyuki
Y
D000447:Aldehydes / Q000737:chemistry; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D000447:Aldehydes; D004952:Esters