Transformations of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline resulting from the action of activated alkynes in trifluoroethanol and hexafluoroisopropanol were studied. In reactions with dimethyl acetylenedicarboxylate, 6-phenylethynyl-substituted benzazocines were prepared, while methyl 4-benzyl-5-(2-ethenylphenyl)-1-methyl-1H-pyrrole-3-carboxylate and benzo[d][3]-azacyclodeca[4,6,7]triene with the allene fragment, respectively, were isolated in reactions with methyl propiolate and acetylacetylene in addition to the corresponding benzazocines. As a rule, in hexafluoroisopropanol, the yields of azocines are higher. In reaction with acetylacetylene in dichloromethane, 1-(2-acetylvinyl)-1-phenylethynyltetrahydroisoquinoline is formed in high yield.
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The work was supported by the RUDN University program '"'5-100" and the Russian Foundation for Basic Research (grants 17-03-00605, 17-53-540001)
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(5), 576–580
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Voskressensky, L.G., Samavati, R., Titov, A.А. et al. Transformation of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline by the action of activated alkynes. Chem Heterocycl Comp 54, 576–580 (2018). https://doi.org/10.1007/s10593-018-2306-y
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DOI: https://doi.org/10.1007/s10593-018-2306-y