Synthetic Route to 4,4a- and 3,4-Dihydroxanthones through [4+2] Cycloaddition and Base-Assisted Sigmatropic Rearrangement
Тип публикации: Journal Article
Дата публикации: 2017-05-18
scimago Q2
wos Q2
white level БС2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Краткое описание
The [4+2] cycloaddition of chromone‐fused dienes with enamines was found to be an efficient method for the synthesis of 4,4a‐ and 3,4‐dihydroxanthone derivatives. Either product type could be obtained by choosing the proper conditions [reaction time and addition of La(NO3)3 as a Lewis acid]. Calculations using density functional theory and Møller–Plesset perturbation theory showed that the isomerization of 4,4a‐dihydroxanthones to 3,4‐dihydroxanthones occurred through a base‐assisted sigmatropic rearrangement. The described reaction provides a convenient route to a natural‐product‐inspired group of 4,4a‐dihydroxanthones with cytotoxic activity.
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Chernov N. M. et al. Synthetic Route to 4,4a- and 3,4-Dihydroxanthones through [4+2] Cycloaddition and Base-Assisted Sigmatropic Rearrangement // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 19. pp. 2836-2841.
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Chernov N. M., Shutov R. V., Sharoyko V., Kuzmich N. N., Belyakov A. V., Yakovlev I. P. Synthetic Route to 4,4a- and 3,4-Dihydroxanthones through [4+2] Cycloaddition and Base-Assisted Sigmatropic Rearrangement // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 19. pp. 2836-2841.
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TY - JOUR
DO - 10.1002/ejoc.201700310
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201700310
TI - Synthetic Route to 4,4a- and 3,4-Dihydroxanthones through [4+2] Cycloaddition and Base-Assisted Sigmatropic Rearrangement
T2 - European Journal of Organic Chemistry
AU - Chernov, Nikita M
AU - Shutov, R V
AU - Sharoyko, Vladimir
AU - Kuzmich, Nikolay N
AU - Belyakov, Alexander V.
AU - Yakovlev, Igor P
PY - 2017
DA - 2017/05/18
PB - Wiley
SP - 2836-2841
IS - 19
VL - 2017
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2017_Chernov,
author = {Nikita M Chernov and R V Shutov and Vladimir Sharoyko and Nikolay N Kuzmich and Alexander V. Belyakov and Igor P Yakovlev},
title = {Synthetic Route to 4,4a- and 3,4-Dihydroxanthones through [4+2] Cycloaddition and Base-Assisted Sigmatropic Rearrangement},
journal = {European Journal of Organic Chemistry},
year = {2017},
volume = {2017},
publisher = {Wiley},
month = {may},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201700310},
number = {19},
pages = {2836--2841},
doi = {10.1002/ejoc.201700310}
}
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Chernov, Nikita M., et al. “Synthetic Route to 4,4a- and 3,4-Dihydroxanthones through [4+2] Cycloaddition and Base-Assisted Sigmatropic Rearrangement.” European Journal of Organic Chemistry, vol. 2017, no. 19, May. 2017, pp. 2836-2841. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201700310.
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