Synthesis, volume 49, issue 16, pages 3700-3709
A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones
Alexander Fisyuk
1, 2
,
Ivan Kulakov
1
,
Anton Shatsauskas
2
,
Mariya Matsukevich
1
,
Irina Palamarchuk
3
,
Tulegen Seilkhanov
1
,
Yuriy Gatilov
4, 5
3
Sh. Ualikhanov Kokshetau State University
|
Publication type: Journal Article
Publication date: 2017-06-07
Catalysis
Organic Chemistry
Abstract
A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[c][1,7]naphthyridin-4(3H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1H)-ones and aromatic aldehydes in a strong acidic media (trifluoroacetic, phosphorous or polyphosphorous acids) under heating. The initial imine derivatives undergo Pictet–Spengler condensation to form intermediate 6-aryl-5,6-dihydrobenzo[c]-1,7-naphthyridin-4(3H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1H)-ones as the final products.
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Fisyuk A. et al. A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones // Synthesis. 2017. Vol. 49. No. 16. pp. 3700-3709.
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Fisyuk A., Kulakov I., Shatsauskas A., Matsukevich M., Palamarchuk I., Seilkhanov T., Gatilov Y. A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones // Synthesis. 2017. Vol. 49. No. 16. pp. 3700-3709.
Cite this
RIS
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TY - JOUR
DO - 10.1055/s-0036-1590470
UR - https://doi.org/10.1055/s-0036-1590470
TI - A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones
T2 - Synthesis
AU - Fisyuk, Alexander
AU - Kulakov, Ivan
AU - Shatsauskas, Anton
AU - Matsukevich, Mariya
AU - Palamarchuk, Irina
AU - Seilkhanov, Tulegen
AU - Gatilov, Yuriy
PY - 2017
DA - 2017/06/07
PB - Georg Thieme Verlag KG
SP - 3700-3709
IS - 16
VL - 49
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex
Copy
@article{2017_Fisyuk,
author = {Alexander Fisyuk and Ivan Kulakov and Anton Shatsauskas and Mariya Matsukevich and Irina Palamarchuk and Tulegen Seilkhanov and Yuriy Gatilov},
title = {A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones},
journal = {Synthesis},
year = {2017},
volume = {49},
publisher = {Georg Thieme Verlag KG},
month = {jun},
url = {https://doi.org/10.1055/s-0036-1590470},
number = {16},
pages = {3700--3709},
doi = {10.1055/s-0036-1590470}
}
Cite this
MLA
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Fisyuk, Alexander, et al. “A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones.” Synthesis, vol. 49, no. 16, Jun. 2017, pp. 3700-3709. https://doi.org/10.1055/s-0036-1590470.
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