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

[Display omitted] 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 i...

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Bibliographic Details
Published in:Mendeleev communications 2022-11, Vol.32 (6), p.729-731
Main Authors: Sagitova, Elena F., Tomilin, Denis N., Sobenina, Lyubov N., Ushakov, Igor A., Apartsin, Konstantin A., Trofimov, Boris A.
Format: Article
Language:English
Subjects:
3-benzylamino-2
4-enyne
benzylamine
tetrahydroindole
tetrahydroindolyldiyne
tetrahydroindolylpyridine
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Summary:[Display omitted] 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.
ISSN:0959-9436
DOI:10.1016/j.mencom.2022.11.007