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Ruthenium‐Catalyzed synthesis of quinolines from anilines and N ‐allylic compounds by cascade amine exchange reaction‐heteroannulation
Author(s) -
Cho Chan Sik,
Ho Oh Byoung,
Shim Sang Chul,
Oh Dae Hee
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370549
Subject(s) - chemistry , allylic rearrangement , catalysis , ruthenium , cascade , amine gas treating , organic chemistry , cascade reaction , combinatorial chemistry , medicinal chemistry , chromatography
Abstract Anilines react with N ‐allylic compounds such as triallylamine and N,N ‐diallylaniline in dioxane in the presence of a catalytic amount of ruthenium(III) chloride hydrate and bis(diphenylphosphino)methane and tin(II) chloride dihydrate to afford the corresponding quinolines in high yields. Several other phosphorus ligands are also effective, but bis(diphenylphosphino)methane is the ligand of choice. A reaction pathway involving cascade amine exchange reaction‐heteroannulation is proposed for this catalytic process.