摘要：

The Beckmann rearrangement of warfarin oxime and the action of hydrazoic acid on warfarin (Schmidt reaction) both yield 3-[α-(acetamidomethyl)benzyl]-4-hydroxycoumarin (II). Acid hydrolysis of II yields 2-(o-hydroxyphenyl)-4-phenyl-1-pyrroline (IV) which was also synthesized by an independent route. The other possible product of the above reactions, 3-[α-(methylcarbamoylmethyl)benzyl]-4-hydroxycoumarin (III), was made from 3-[α-(carboxymethyl)benzyl]-4-hydroxycoumarin (X), a new compound. The structure of X was proved by conversion to warfarin (I) via 3-(α-acetonylbenzyl)-4-methoxycoumarin (XV).

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