E. F. Sagitova, D. N. Tomilin, L. N. Sobenina, I. A. Ushakov, K. A. Apartsin, B. A. Trofimov, “Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines”, Mendeleev Commun., 2022, Volume 32, Issue 6,Pages <nobr>729

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Communications

Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines

E. F. Sagitova^a, D. N. Tomilin^a, L. N. Sobenina^a, I. A. Ushakov^a, K. A. Apartsin^b, B. A. Trofimov^a

^a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
^b Biomedical Research and Technology Department of the Irkutsk Scientific Center, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation

Abstract: 1-Acyl-4-tetrahydroindolyldiynes (available from cross-coupling of 4,5,6,7-tetrahydroindole with 1-acyl-4-bromo-1,3-diynes) undergo oxidative [4+2]-cycloaddition with benzylamine in KOH/DMSO or K3PO4/DMSO systems (80°C, 4 h) to afford 2-acyl-6-phenyl-5-tetrahydroindolyl-pyridines in ∼40% yields. Non-catalyzed reaction of the same reactants in boiling MeOH (4 h) or in DABCO/MeCN system (reflux, 1 h) gives 3-benzylaminoalk-2-en-4-ynones in ∼40% yields.

Keywords: tetrahydroindole, tetrahydroindolyldiyne, benzylamine, tetrahydroindolylpyridine, 3-benzylamino-2, 4-enyne.

Language: English

DOI: 10.1016/j.mencom.2022.11.007

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