Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Rearrangement of Isoflavanone Oximes with Lithium Aluminum Hydride
Naoto InoueShozo YamaguchiShoei ItoIkuko Suzuki
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1968 Volume 41 Issue 9 Pages 2078-2082

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Abstract

The reaction of isoflavanone oxime (III), 7-methoxyisoflavanone oxime (IV), and 4′,7-dimethoxyisoflavanone oxime (V) with lithium aluminum hydride in ether for 20 hr under refluxing gave 3-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepine derivatives (XVII, XVIII and XIX) but not the expected 4-aminoisoflavans. When a similar reaction was carried out using flavanone oxime and 7-methoxyflavanone oxime, only 4-aminoflavans were obtained, and the rearrangement reaction observed in isoflavanone oximes did not occur. Therefore, it may be considered that, in the reaction of chromanone oximes and lithium aluminum hydride, the position (C2 or C3) and the size of the substituent exerts a remarkable influence on the rearrangement reaction, while the methoxyl group at the 7-position (para position to the oximino group) has little effect.

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