Abstract
It has been found that aceto- and benzonitriles and 3,4-dimethoxyphenylacetone in the presence of acetylperchlorate or upon heating in polyphosphoric acid or polyphosphoric ester form the corresponding isoquinoline. The data indicate that the reaction proceeds like a typical Ritter reaction and is defined by electrophilic activation of the carbonyl group of the ketone and the nucleophilicity of the nitrile. This methodology gave the alkaloid dioxyline (dimoxyline), obtained in high yield by the use of benzoylhexachloroantimonate.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 363–368, March, 1992.
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Brovchenko, V.G., Shibaeva, N.V., Pyshchev, A.I. et al. Synthesis of the alkaloid dioxyline and other 6,7-dimethoxyisoquinolines in a modified ritter reaction. Chem Heterocycl Compd 28, 304–308 (1992). https://doi.org/10.1007/BF00529374
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DOI: https://doi.org/10.1007/BF00529374