化学療法剤の合成研究(第8報), 1,9b-Dihydro-2H, 4H-2-oxo-azeto[1,2-c][1,3]benzoxazine-4-carboxylic Acid誘導体の立体選択的合成 : 複素環式化合物の合成研究第813報

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Cyclization of the diastereoisomeric mixture of 2,2,2-trichloro- and p-nitrobenzyl 2-hydroxy-2-[cis-4-(2-hydroxyphenyl)-2-oxo-3-phthalimido-1-azetidinyl] acetates (17 and 18) gave stereoselectively the corresponding 1,2-benzo-3-oxacephams (20 and 26) together with 21,a stereoisomer of 20. The starting compounds (17 and 18) were prepared via the cycloaddition reaction of N-(2-benzyloxybenzylidene)-2,4-dimethoxybenzylamine (8) with phthaloylglycyl chloride, followed by oxidative cleavage of 2,4-dimethoxybenzyl group of the adduct (9). Deprotection of the N-phthaloyl and ester groups of 20 and 26 was also investigated and 1-amino-1,9b-dihydro-2H, 4H-2-oxoazeto [1,2-c] [1,3] benzoxazine-4-carboxylate (22) and 1,9b-dihydro-2H, 4H-2-oxo-1-phthalimidoazeto [1,2-c] [1,3] benzoxazine-4-carboxylic acid (27) were obtained.
社団法人日本薬学会の論文
1979-11-25