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Synthesis of Fused and Linked Bicyclic Nitrogen Heterocycles by Palladium‐Catalyzed Domino Cyclization of Propargyl Bromides
Author(s) -
Okano Akinori,
Tsukamoto Koji,
Kosaka Shohei,
Maeda Hatsuo,
Oishi Shinya,
Tanaka Tetsuaki,
Fujii Nobutaka,
Ohno Hiroaki
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000653
Subject(s) - bicyclic molecule , propargyl , palladium , chemistry , nucleophile , catalysis , domino , medicinal chemistry , organic chemistry , combinatorial chemistry
The palladium(0)‐catalyzed direct construction of bicyclic heterocycles is described. Treatment of propargyl bromides that have nucleophilic functional groups connected by two or three carbon atoms with catalytic [Pd(PPh 3 ) 4 ] affords bis‐cyclization products in good yields. The desired bicyclic heterocycles can be obtained selectively when using substrates with appropriate nucleophilic groups. We also describe the reaction of a 2‐alkynylazetidine derivative with a catalytic amount of [Pd(PPh 3 ) 4 ] under base‐free conditions, which affords the same fused heterocycles as the corresponding propargyl bromides.