Phenolic Cyclizationによる1-スピロイソキノリン誘導体の合成 : 複素環式化合物の合成研究第335報

概要

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Syntheses of 1-spiroalkano-, 1-spiroheteroalkano-, and 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines are described. 3-(2-Aminoethyl)phenol as a starting material was synthesized as follows. Demethylation of m-methoxyphenylacetonitrile, which was obtained by benzyne reaction of o-chloroanisole with acetonitrile, with pyridine hydrochloride gave m-hydroxyphenylacetonitrile, whose ethanolic solution saturated with ammonia was hydrogenated in the presence of Raney nickel and gave the expected 3-(2-aminoethyl)phenol. On the other hand, one cycloalkanone, cyclohexanone, three heterocyclic ketones, 1-methyl-4-piperidone, 1-benzyl-4-piperidone, and 2,3,5,6-tetrahydro-1,4-thiapyrone, and four noncyclic ketones, acetone, ethyl methyl ketone, benzaldehyde, and acetophenone, were used as one of the starting materials, followed by usual phenolic cyclization, to afford eight kinds of the corresponding new tetrahydroisoquinolines.
公益社団法人日本薬学会の論文
1969-11-25