Synthesis of five-, six-, and seven-membered ring lactams by CpRh complex-catalyzed oxidative N-heterocyclization of amino alcohols |
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Authors: | Fujita Ken-ichi Takahashi Yoshinori Owaki Maki Yamamoto Kazunari Yamaguchi Ryohei |
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Affiliation: | Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan. fujitak@kagaku.mbox.media.kyoto-u.ac.jp |
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Abstract: | A new effective catalytic system consisting of [CpRhCl(2)](2)/K(2)CO(3) (Cp = pentamethylcyclopentadienyl) for the lactamization of amino alcohols has been developed. As an example, the reaction of 3-(2-aminophenyl)-1-propanol in the presence of [CpRhCl(2)](2) (5.0% Rh) and K(2)CO(3) (10%) in acetone gives 3,4-dihydro-2(1H)-quinolinone in an isolated yield of 80%. A variety of five-, six-, and seven-membered benzo-fused lactams are synthesized by this catalytic system. [reaction: see text] |
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