From 3-Acyl-2-methylindoles to γ-Carbolines: Li-Promoted Cycloaddition Reaction and Its Quantum Chemical Study
Publication type: Journal Article
Publication date: 2019-10-08
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31593465
Organic Chemistry
Abstract
A one-pot cycloaddition strategy for obtaining γ-carbolines under mild conditions was developed. The reaction represents a new approach to the annulation of a pyridine ring to an indole core. Treating 2-methyl-3-benzoylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The organolithium compounds generated were found to react with nitriles. The resulting 4,5-dihydro-1H-pyrido[4,3-b]indol-1-ols undergo spontaneous water elimination to give the corresponding γ-carbolines. The applicability of this reaction for the synthesis of isoquinolines has been shown. For the first time, a lithium atom was found to be part of an eight-centered polycyclic transition state according to a detailed DFT PCM/DFT/B3LYP/6-311++G(d,p) and ab initio PCM/MP2//HF/6-311++G(d,p) quantum chemical study.
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Citations from 2024:
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Gazizova J. V. et al. From 3-Acyl-2-methylindoles to γ-Carbolines: Li-Promoted Cycloaddition Reaction and Its Quantum Chemical Study // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 13721-13732.
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Gazizova J. V., Suzdalev K. F., Lisovin A. V., Kletskii M. E., Burov O. N., Kurbatov S. V. From 3-Acyl-2-methylindoles to γ-Carbolines: Li-Promoted Cycloaddition Reaction and Its Quantum Chemical Study // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 13721-13732.
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TY - JOUR
DO - 10.1021/acs.joc.9b01926
UR - https://doi.org/10.1021/acs.joc.9b01926
TI - From 3-Acyl-2-methylindoles to γ-Carbolines: Li-Promoted Cycloaddition Reaction and Its Quantum Chemical Study
T2 - Journal of Organic Chemistry
AU - Gazizova, Julia V
AU - Suzdalev, Konstantin F
AU - Lisovin, Anton V
AU - Kletskii, Mikhail E
AU - Burov, Oleg N
AU - Kurbatov, Sergey V.
PY - 2019
DA - 2019/10/08
PB - American Chemical Society (ACS)
SP - 13721-13732
IS - 21
VL - 84
PMID - 31593465
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2019_Gazizova,
author = {Julia V Gazizova and Konstantin F Suzdalev and Anton V Lisovin and Mikhail E Kletskii and Oleg N Burov and Sergey V. Kurbatov},
title = {From 3-Acyl-2-methylindoles to γ-Carbolines: Li-Promoted Cycloaddition Reaction and Its Quantum Chemical Study},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.9b01926},
number = {21},
pages = {13721--13732},
doi = {10.1021/acs.joc.9b01926}
}
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Gazizova, Julia V., et al. “From 3-Acyl-2-methylindoles to γ-Carbolines: Li-Promoted Cycloaddition Reaction and Its Quantum Chemical Study.” Journal of Organic Chemistry, vol. 84, no. 21, Oct. 2019, pp. 13721-13732. https://doi.org/10.1021/acs.joc.9b01926.