Open Access
An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes
Publication type: Journal Article
Publication date: 2021-12-04
PubMed ID:
34885948
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
The catalytic olefination reaction of 2-nitrobenzaldehydes with CF3CCl3 afforded stereoselectively trifluoromethylated ortho-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF3-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H2O system initiated intramolecular cyclization to afford 2-CF3-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2- CF3-indole.
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Total citations:
7
Citations from 2024:
4
(57.14%)
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GOST
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Muzalevskiy V. M. et al. An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes // Molecules. 2021. Vol. 26. No. 23. p. 7365.
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Muzalevskiy V. M., Sizova Z. A., Abaev V. T., Nenajdenko V. G. An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes // Molecules. 2021. Vol. 26. No. 23. p. 7365.
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RIS
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TY - JOUR
DO - 10.3390/molecules26237365
UR - https://doi.org/10.3390/molecules26237365
TI - An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes
T2 - Molecules
AU - Muzalevskiy, Vasiliy M
AU - Sizova, Zoia A
AU - Abaev, Vladimir T
AU - Nenajdenko, Valentine G.
PY - 2021
DA - 2021/12/04
PB - MDPI
SP - 7365
IS - 23
VL - 26
PMID - 34885948
SN - 1420-3049
ER -
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BibTex (up to 50 authors)
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@article{2021_Muzalevskiy,
author = {Vasiliy M Muzalevskiy and Zoia A Sizova and Vladimir T Abaev and Valentine G. Nenajdenko},
title = {An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {MDPI},
month = {dec},
url = {https://doi.org/10.3390/molecules26237365},
number = {23},
pages = {7365},
doi = {10.3390/molecules26237365}
}
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MLA
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Muzalevskiy, Vasiliy M., et al. “An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes.” Molecules, vol. 26, no. 23, Dec. 2021, p. 7365. https://doi.org/10.3390/molecules26237365.