Direct construction of bicyclic heterocycles by palladium-catalyzed domino cyclization of propargyl bromides.
The palladium-catalyzed domino cyclization of propargyl bromides having two nucleophilic functional groups is described. Treatment of 1,7-diamino-5-bromohept-3-yne derivatives with catalytic Pd(PPh3)4 in the presence of NaH in MeOH gives the 2,7-diazabicyclo[4.3.0]non-5-enes in good yields. Interestingly, the regioselectivity of the reaction is completely controlled by the relative reactivity of the amine functional groups, irrespective of the position of the nucleophiles. The malonate derivative also undergoes domino cyclization to produce a hexahydroindole derivative.
Ohno
Hiroaki
H
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. hohno@pharm.kyoto-u.ac.jp
Okano
Akinori
A
Kosaka
Shohei
S
Tsukamoto
Koji
K
Ohata
Miyo
M
Ishihara
Kotaro
K
Maeda
Hatsuo
H
Tanaka
Tetsuaki
T
Fujii
Nobutaka
N
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D010165:Palladium / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D010165:Palladium; D010293:Pargyline; C458239:propargyl bromide