Syntheses of 5, 5'-Methylenebisisoxazole Derivative and Its Reactions with Electrophiles

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A potential tetra-β A-ketide compound, 5, 5'-methylenebisisoxazole-3, 3'-dicarboxylate (IV) was prepared from 1, 4-pentadiyne (I) and carboethoxynitriloxide (II). The bisisoxazole (IV) was also synthesized by way of diethyl 5, 5'-methylene-bis (2-isoxazoline)-3, 3'-dicarboxylate (VII)(racemi) and (VIII)(meso). The methylene hydrogens of the compound (IV) was shown to have a nature of an active methylene group and to react with various electrophiles. The four position of the isoxazole ring of IV had also nucleophilic character, which was useful for obtaining a cyclohexane derivative. A possibility was presented that the compound (IV) could be an important starting material for a synthesis of poly β-diketone system.

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