Summary
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1.
By the catalytic condensation of 2-phenyl-5-hexen-3-yn-2-ol with ammonia, and also that of acetophenone with 1-buten-3-yne and ammonia, over a Cd3(PO4)2/Al2O3 catalyst at 400 % 6-phenyl-2-picoline was obtained.
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2.
By the analogous reactions of 4′-methylacetophenone, 4′-ethylacetophenone, and pinacolone with 1-buten-3-yne and ammonia, 6-p-tolyl-, 6-p-ethylphenyl-, and 6-t-butyl-2-picolines were obtained.
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Literature cited
I. L. Kotlyarevskii and L. I. Vereshchagin, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 715 (1959); No. 7 (1960).
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R. Frank and R. Meikle, J. Am. Chem. Soc.72, 4184 (1960).
M. Scholtz, Ber.28, 1726 (1895).
M. Ferles and I. Jizba, Chemie pyridinu, Praha (1957) pp. 82 and 88.
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Vereshchagin, L.I., Kotlyarevskii, I.L. Synthesis of pyridine bases from 1-buten-3-yne. Russ Chem Bull 9, 1338–1341 (1960). https://doi.org/10.1007/BF00907666
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DOI: https://doi.org/10.1007/BF00907666