Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2H-Pyran-5-carbonitriles
Тип публикации: Journal Article
Дата публикации: 2021-05-20
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 5.8
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
34014677
Organic Chemistry
Краткое описание
A library of trans-4,5-dihydrofuran-3-carbonitriles was synthesized in a diastereoselective manner in good yields by the three-component reaction of β-ketonitriles, carbonyl- and semistabilized pyridinium ylide precursors, and aldehydes in the presence of piperidine. This one-pot transformation generates two C-C and one C-O bond and proceeds through a cascade Knoevenagel condensation, a Michael addition, and intramolecular SN2 cyclization. Formation of cyclopropanecarbonitrile derivatives, which in some cases were obtained as major products, was found to be a competing reaction. The use of arylglyoxals changes regioselectivity and leads to 2-hydroxy-2H-pyran-5-carbonitriles.
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Demidov M. R. et al. Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2H-Pyran-5-carbonitriles // Journal of Organic Chemistry. 2021. Vol. 86. No. 11. pp. 7460-7476.
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Demidov M. R., Osyanin V. A., Osyanin V. A., Klimochkin Y. Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2H-Pyran-5-carbonitriles // Journal of Organic Chemistry. 2021. Vol. 86. No. 11. pp. 7460-7476.
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TY - JOUR
DO - 10.1021/acs.joc.1c00423
UR - https://doi.org/10.1021/acs.joc.1c00423
TI - Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2H-Pyran-5-carbonitriles
T2 - Journal of Organic Chemistry
AU - Demidov, Maxim R
AU - Osyanin, Vitaly A
AU - Osyanin, Vitaly A.
AU - Klimochkin, Yuri
PY - 2021
DA - 2021/05/20
PB - American Chemical Society (ACS)
SP - 7460-7476
IS - 11
VL - 86
PMID - 34014677
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Demidov,
author = {Maxim R Demidov and Vitaly A Osyanin and Vitaly A. Osyanin and Yuri Klimochkin},
title = {Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2H-Pyran-5-carbonitriles},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.joc.1c00423},
number = {11},
pages = {7460--7476},
doi = {10.1021/acs.joc.1c00423}
}
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Demidov, Maxim R., et al. “Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2H-Pyran-5-carbonitriles.” Journal of Organic Chemistry, vol. 86, no. 11, May. 2021, pp. 7460-7476. https://doi.org/10.1021/acs.joc.1c00423.
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