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Preparation of New Nitrogen-bridged Heterocycles. 6. First Synthesis of 2-Aroylfuro[2,3- b ]indolizine Derivatives

1983; Oxford University Press; Volume: 56; Issue: 4 Linguagem: Inglês

10.1246/bcsj.56.1219

1348-0634

Akikazu Kakehi, Suketaka Ito, Tsuyoshi Ohizumi, Masayoshi Ito,

Chemical synthesis and alkaloids

Abstract Alkaline treatment of 2-(aroylmethoxy)-3-(2,2-dicyanovinyl)indolizine derivatives, readily available from the step-by-step reactions of 1-(ethoxycarbonylmethyl)-2-picolinium salts with a base, (ethoxymethylene)malononitrile followed by some phenacyl bromides in ethanol, afforded smoothly the title compounds, 2-aroylfuro[2,3-b]indolizine derivatives, in good yields. These furoindolizines could be also obtained directly from the pyridinium salts without the isolation of intermediate 3-vinylindolizines. Formation mechanisms and some physical properties of these furoindolizines are also discussed.