Reductive Cyclizationによる8-Aza-6-oxa-8-methyl-3,4-benzbicyclo[3,2,1]octaneの合成 : 複素環式化合物の合成研究第190報

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Reduction of methyl 2-methyl-3,4-dihydroisocarbostyril-3-carboxylate (XVI) with lithium aluminum hydride gave a mixture of 3-hydroxymethyl-2-methyl-3,4-dihydroisocarbostyril (XVII), 3-hydroxymethyl-2-methyl-1,2,3,4-tetrahydroisoquinoline (XIX), and 8-aza-6-oxa 8methyl-3,4-benzbicyclo[3,2,1] octane (XVIII). The latter two compounds (XIX and XVIII) were also obtained by the reduction of XVII with lithium aluminum hydride. It is of particular interest that the reductive oxygenation of XVI and XVII with lithium aluminum hydride gave a cyclized compound having an oxazolidine ring system, but attempts to obtain the expected diazocine derivative (XXVII) by the reductive cyclization of 3-aminoethyl-2-methyl-3,4-dihydroisocarbostyril (XXVI) resulted in failure, affording 1,2,3,4,-tetrahydroisoquinoline derivative (XXVIII), which was charaterized as its dipicrate and assigned by NMR spectrum.
公益社団法人日本薬学会の論文
1967-08-25