A facile synthesis of colchiceine analogues (4-(1-acetamido-3-arylpropyl)tropolones).

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概要

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• The condensation of 4-acetyltropolone with various arenecarbaldehydes gave a wide variety of 4-cinnamoyltropolone derivatives in good yield. The same reaction with 2-furaldehyde and cinnamaldehyde also afforded the corresponding 4-substituted tropolones. These products were converted to their oximes (with hydroxylamine hydrochloride), which in turn were hydro genated over 5% Pd/C in acetic acid and then acetylated with acetic anhydride, to yield 4-(1-acetamido-3-aryl-2-propenyl)tropolones. The catalytic hydrogenation of these olefinic products over 10–30% Pd/C in aqueous KOH gave various 4-(1-acetamido-3-arylpropyl)tropolones,which possess a B-ring-open structure of colchiceine. The structures of these products are discussed on the basis of UV, IR, and <SUP>1</SUP>H-NMR spectra.

• 公益社団法人 日本化学会の論文

著者

• Takase Kahei

  Department Of Chemistry Faculty Of Science Tohoku University

• Yamamoto Hiroshi

  Departmemt Of Chemical Engineering University Of Tokyo

• Nozoe Tetsuo

  Department of Chemistry Faculty of Science Tohoku University

• Asao Toyonobu

  Department of Chemistry Faculty of Science Tohoku University

• Kawabe Norio

  Department of Chemistry, Faculty of Science, Tohoku University

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