Journal of Organic Chemistry, volume 86, issue 9, pages 6888-6896

An Isoxazole Strategy for the Synthesis of Fully Substituted Nicotinates

Publication typeJournal Article
Publication date2021-04-13
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor3.6
ISSN00223263, 15206904
Organic Chemistry
Abstract
A four-step quasi one-pot procedure for the preparation of fully substituted nicotinates from ketone enamines and 4-methylideneisoxazol-5-ones has been developed. The reaction sequence involves (1) reaction of 4-methylideneisoxazol-5-ones with ketone enamines with the formation of isoxazole-5-ols, (2) their O-methylation with diazomethane, (3) hydrogenative cleavage of the O-N bond in 5-methoxyisoxazoles under action of Mo(CO)6/H2O and simultaneous isomerization and condensation of the formed enamines, with the formation of dihydropyridines, and (4) aromatization of the latter.

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GOST |
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GOST Copy
Galenko E. E. et al. An Isoxazole Strategy for the Synthesis of Fully Substituted Nicotinates // Journal of Organic Chemistry. 2021. Vol. 86. No. 9. pp. 6888-6896.
GOST all authors (up to 50) Copy
Galenko E. E., Kryukova M. A., Novikov M. S., Khlebnikov A. F. An Isoxazole Strategy for the Synthesis of Fully Substituted Nicotinates // Journal of Organic Chemistry. 2021. Vol. 86. No. 9. pp. 6888-6896.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.joc.1c00286
UR - https://doi.org/10.1021%2Facs.joc.1c00286
TI - An Isoxazole Strategy for the Synthesis of Fully Substituted Nicotinates
T2 - Journal of Organic Chemistry
AU - Galenko, Ekaterina E
AU - Kryukova, Mariya A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2021
DA - 2021/04/13 00:00:00
PB - American Chemical Society (ACS)
SP - 6888-6896
IS - 9
VL - 86
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
Cite this
BibTex Copy
@article{2021_Galenko,
author = {Ekaterina E Galenko and Mariya A Kryukova and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {An Isoxazole Strategy for the Synthesis of Fully Substituted Nicotinates},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021%2Facs.joc.1c00286},
number = {9},
pages = {6888--6896},
doi = {10.1021/acs.joc.1c00286}
}
MLA
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MLA Copy
Galenko, Ekaterina E., et al. “An Isoxazole Strategy for the Synthesis of Fully Substituted Nicotinates.” Journal of Organic Chemistry, vol. 86, no. 9, Apr. 2021, pp. 6888-6896. https://doi.org/10.1021%2Facs.joc.1c00286.
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