One-pot synthesis of aminoenone via direct reaction of the chloroalkyl enone with NaN3: rapid access to polycyclic alkaloids.
A new one-pot procedure for the preparation of aminoenone from chloroalkyl enone and sodium azide was demonstrated. The structure of the presumed triazoline intermediate in this process was confirmed by X-ray analysis for the first time. As the application of this methodology, the synthesis of polycyclic alkaloid hexahydroapoerysopine (1a) was achieved through an efficient synthetic route.
Zhao
Yu-Ming
YM
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Gu
Peiming
P
Tu
Yong-Qiang
YQ
Zhang
Hai-Jun
HJ
Zhang
Qing-Wei
QW
Fan
Chun-An
CA
D000470:Alkaloids / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009584:Nitrogen / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D000470:Alkaloids; D000588:Amines; C003320:sodium nitride; D009584:Nitrogen