title: Direct construction of bicyclic heterocycles by palladium-catalyzed domino cyclization of propargyl bromides.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. hohno@pharm.kyoto-u.ac.jp
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
authors.forename: Akinori
authors.initials: A
authors.lastname: Okano
authors.forename: Shohei
authors.initials: S
authors.lastname: Kosaka
authors.forename: Koji
authors.initials: K
authors.lastname: Tsukamoto
authors.forename: Miyo
authors.initials: M
authors.lastname: Ohata
authors.forename: Kotaro
authors.initials: K
authors.lastname: Ishihara
authors.forename: Hatsuo
authors.initials: H
authors.lastname: Maeda
authors.forename: Tetsuaki
authors.initials: T
authors.lastname: Tanaka
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D010165:Palladium / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D010165:Palladium; D010293:Pargyline; C458239:propargyl bromide