A New Cyclization Reaction of Cyclic Ketoxime.

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When treated with phosphoryl chloride in boiling toluene 2-veratrylcyclopentanone oxime suffered an intramolecular dehydration, in which oxime-OH took part, to form 6, 7-dimeth-oxy-2, 3, 9, 9a-tetrahydro-1H-cyclopenta [b] quinoline. Spontaneous dehydrogenation of the latter resulted in the formation of 6, 7-dimethoxy-2, 3-dihydro-1H-cyclopenta [b] quinoline as the ultimate product. 2-Veratrylcyclohexanone oxime behaved similarly, but gave an inferior yield of 6, 7-dimethoxy-1, 2, 3, 4-tetrahydroacridine. Both products were identified with the authentic specimens. This is a novel dehydration reaction of an oxime.

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