期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 11, 页码 4101-4109出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo800249f
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The use of a powerful aminobenzannulation reaction has been applied for the synthesis of amino-substituted quinolines, dibenzofurans, and carbazoles. The precursors are heterocycles bearing a methyl ketone group ortho to an internal alkyne. They are commercially available or can be obtained in three to four classical and efficient reactions: Vilsmeier-Haack, Sonogashira (diversity point), Grignard, and Ley's oxidation. Upon aminobenzannulation reaction-classical conditions being pyrrolidine neat or in a solvent and 4 A MS-an interesting range of disubstituted quinolines, dibenzofurans, and carbazoles are obtained along with enamine formation in some cases. The reaction is useful since meta-substituted heterocycles are produced and also differs from classical heterocyclic methods which go through closure at the heteroatom-containing ring instead of benzene ring formation.
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