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.
Top-30
Citations by journals
|
1
2
3
|
|
|
Synthesis
3 publications, 20%
|
|
|
Russian Journal of Organic Chemistry
2 publications, 13.33%
|
|
|
Dyes and Pigments
2 publications, 13.33%
|
|
|
Journal of Molecular Structure
1 publication, 6.67%
|
|
|
Doklady Chemistry
1 publication, 6.67%
|
|
|
Journal of Organic Chemistry
1 publication, 6.67%
|
|
|
Topics in Current Chemistry
1 publication, 6.67%
|
|
|
Chemistry of Heterocyclic Compounds
1 publication, 6.67%
|
|
|
ChemistrySelect
1 publication, 6.67%
|
|
|
Russian Journal of General Chemistry
1 publication, 6.67%
|
|
|
ACS Catalysis
1 publication, 6.67%
|
|
|
1
2
3
|
Citations by publishers
|
1
2
3
4
|
|
|
Pleiades Publishing
4 publications, 26.67%
|
|
|
Elsevier
3 publications, 20%
|
|
|
Thieme
3 publications, 20%
|
|
|
American Chemical Society (ACS)
2 publications, 13.33%
|
|
|
Springer Nature
2 publications, 13.33%
|
|
|
Wiley
1 publication, 6.67%
|
|
|
1
2
3
4
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0],"imageUrls":["","","","","","",""],"datasets":[{"label":"Citations number","data":[2,0,2,4,4,1,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["13.33",0,"13.33","26.67","26.67","6.67","13.33"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Synthesis","Russian Journal of Organic Chemistry","Dyes and Pigments","Journal of Molecular Structure","Doklady Chemistry","Journal of Organic Chemistry","Topics in Current Chemistry","Chemistry of Heterocyclic Compounds","ChemistrySelect","Russian Journal of General Chemistry","ACS Catalysis"],"ids":[10934,5728,10101,9347,11308,8697,23927,16828,8021,13581,4873],"codes":[0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp"],"datasets":[{"label":"","data":[3,2,2,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[20,13.33,13.33,6.67,6.67,6.67,6.67,6.67,6.67,6.67,6.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Pleiades Publishing","Elsevier","Thieme","American Chemical Society (ACS)","Springer Nature","Wiley"],"ids":[101,17,135,40,8,11],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp"],"datasets":[{"label":"","data":[4,3,3,2,2,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[26.67,20,20,13.33,13.33,6.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[1,0,1,0,2,0,0],"percentage":["6.67","0","6.67","0","13.33","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,1,0,0,0],"percentage":["0","0","0","6.67","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,0,0,1,0,0,0],"percentage":["6.67","0","0","6.67","0","0","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[0,0,1,2,2,1,2],"percentage":["0","0","6.67","13.33","13.33","6.67","13.33"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[1,0,1,0,2,0,0],"percentage":["6.67","0","6.67","0","13.33","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,2,0,0,0],"percentage":["0","0","0","13.33","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,0,0,0,1,1,1],"percentage":["6.67","0","0","0","6.67","6.67","6.67"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[0,0,1,2,1,0,1],"percentage":["0","0","6.67","13.33","6.67","0","6.67"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0,0,0,0],"percentage":["0","0","0","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
GOST all authors (up to 50)
Copy
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
Copy
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 - Thieme
SP - 3700-3709
IS - 16
VL - 49
SN - 0039-7881
SN - 1437-210X
ER -
Cite this
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 = {Thieme},
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
Copy
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.
Profiles