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

, 
Denis Nikolaevich Tomilin 1
Denis Nikolaevich Tomilin
,  , 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Konstantin A Apartsin 2
Konstantin A Apartsin
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
2 Biomedical Research and Technology Department of the Irkutsk Scientific Center, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
10.1016/j.mencom.2022.11.007
Published 2022-10-21
Communication , Volume 32, Issue 6, 729-731
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Sagitova E. F. et al. 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 Communications. 2022. Vol. 32. No. 6. pp. 729-731.
GOST all authors (up to 50) Copy
Sagitova E. F., Tomilin D. N., Sobenina L. N., Ushakov I. A., Apartsin K. A., Trofimov B. A. 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 Communications. 2022. Vol. 32. No. 6. pp. 729-731.
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TY - JOUR
DO - 10.1016/j.mencom.2022.11.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.007
TI - Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines
T2 - Mendeleev Communications
AU - Sagitova, Elena Faritovna
AU - Tomilin, Denis Nikolaevich
AU - Sobenina, Lyubov Nikolaevna
AU - Ushakov, Igor Alekseevich
AU - Apartsin, Konstantin A
AU - Trofimov, Boris Aleksandrovich
PY - 2022
DA - 2022/10/21
PB - Mendeleev Communications
SP - 729-731
IS - 6
VL - 32
ER -
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@article{2022_Sagitova,
author = {Elena Faritovna Sagitova and Denis Nikolaevich Tomilin and Lyubov Nikolaevna Sobenina and Igor Alekseevich Ushakov and Konstantin A Apartsin and Boris Aleksandrovich Trofimov},
title = {Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.007},
number = {6},
pages = {729--731},
doi = {10.1016/j.mencom.2022.11.007}
}
MLA
Cite this
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Sagitova, Elena Faritovna, et al. “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 Communications, vol. 32, no. 6, Oct. 2022, pp. 729-731. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.007.

Keywords

3-benzylamino-2
4-enyne
benzylamine
tetrahydroindole
tetrahydroindolyldiyne
tetrahydroindolylpyridine

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.

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