The mechanism of warfarin formation from 4-hydroxycoumarin and β-anilinobenzylacetone. Evidence for schiff base intermediates showing enhanced reactivity in the Michael reaction
✍ Scribed by Collin Schroeder; Seymour Preis; Karl Paul Link
- Publisher
- Elsevier Science
- Year
- 1960
- Tongue
- French
- Weight
- 338 KB
- Volume
- 1
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
PREVlOUS kinetic studies' have shown that the formation of warfarin (I) from 4-hydroxycoumarin (II) and S-anilinobenzglacetone (III) in the presence of aniline (reaction 1) is more rapid (ca. double at equivalent concentrations) ? 'cs"a C6 H,-fkl-CH&-CH3 CgHg -NH2 C6H5-NH x 'III I than its formation from 4-hydroxycoumarin and benzalacetone (IV) in the presence of aniline (reaction 2). 1 In the Japanese Patent Court demandant Toko Chemical Co., Ltd., Tokyo, Japan, for H. Naruke "on the scope of right of patent number 195, Ok0 held by Wisconsin Alumni Research Foundation, Madison 5, Wisconsin, Trial No. 3800/1953" dated October 26, 1953, it is asserted that the formation of narfarin from 4-hydroqxoumarin and B-anilinobenzylacetone is a direct (S > reaction. 2 2 The chemical name 3-(cc-acetonylbenzyl)-4-hydroxycoumari.n is the systematic name selected by Chemical Abstracts for the anticoagulant warfarin.