複素環式化合物の合成研究(第476報)Camptothecin関連化合物の合成研究(第4報)8-Cyano-7-ethoxycarbonyl-9,11-dihydro-9,11-dioxoindolizino[1,2-b]quinolineの合成

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In order to obtain 2,6-dicyano-7-ethoxycarbonyl-1,5-dioxo-1,2,3,5-tetrahydroindolizine as an intermediate for the synthesis of camptothecin, Michael condensation of methyl 3-cyano-4-ethoxycarbonyl-1,2-dihydro-2-oxopyridine-6-carboxylate (V) with acrylonitrile was carried out but failed to afford the objective substance. A similar condensation of V with t-butyl acrylate also resulted in failure. Ethyl 5-cyano-4-ethoxycarbonyl-5-oxo1,6-dihydro-2-pyridine glyoxylate (VIII) was synthesized by the reaction of 3-cyano-4-ethoxycarbonyl-1,2-dihydro-2-oxopyridine-6-carboxylic acid chloride with ethyl t-butylmalonate. Although cyclization of VIII to ethyl 6-cyano-1,2,3,5-tetrahydro-1,3,5-trioxo-7-indolizine carboxylate (IX) was unsuccessful, Friedlander reaction of VIII with 2-aminobenzaldehyde gave the expected 8-cyano-7-ethoxycarbonyl-9,11-dihydro-9,11-dioxoindolizino[1,2-b]quinoline (X) in one step.
社団法人日本薬学会の論文
1972-07-25