A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines
Alexander S. Fisyuk
1, 2
,
Anton L. Shatsauskas
1, 2, 3
,
Sergey A. Kirnosov
1, 4
,
Ekaterina S. Keyn
1, 4
,
Vladislav Yu. Shuvalov
1, 2, 5
,
Anastasia S. Kostyuchenko
2
3
Chemical Technology and Biotechnology, Omskij gosudarstvennyj tehniceskij universitet, Omsk, Russian Federation
|
Publication type: Journal Article
Publication date: 2024-05-10
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Abstract
Two approaches were proposed for the synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones. The one-step method based on the Pictet–Spengler reaction of 3-amino-2-phenylquinolin-4(1H)-one with aromatic aldehydes requires heating in a strong acidic media, which leads to significant limitations on the possible products. The second approach is based on the conversion of 3-amino-2-phenylquinolin-4(1H)-one to 4-phenyl[1,3]oxazolo[4,5-c]quinolines followed by rearrangement under the action of AlCl3. A significant advantage of the two-step synthesis is the possibility of obtaining a wider range of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones, including those not available using the Pictet–Spengler reaction.
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Total citations:
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Citations from 2024:
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(100%)
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Shatsauskas A. L. et al. A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines // Synthesis. 2024. Vol. 56. No. 13. pp. 2100-2108.
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Fisyuk A. S., Shatsauskas A. L., Kirnosov S. A., Keyn E. S., Shuvalov V. Y., Kostyuchenko A. S. A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines // Synthesis. 2024. Vol. 56. No. 13. pp. 2100-2108.
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TY - JOUR
DO - 10.1055/a-2323-0770
UR - http://www.thieme-connect.de/DOI/DOI?10.1055/a-2323-0770
TI - A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines
T2 - Synthesis
AU - Fisyuk, Alexander S.
AU - Shatsauskas, Anton L.
AU - Kirnosov, Sergey A.
AU - Keyn, Ekaterina S.
AU - Shuvalov, Vladislav Yu.
AU - Kostyuchenko, Anastasia S.
PY - 2024
DA - 2024/05/10
PB - Georg Thieme Verlag KG
SP - 2100-2108
IS - 13
VL - 56
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2024_Shatsauskas,
author = {Alexander S. Fisyuk and Anton L. Shatsauskas and Sergey A. Kirnosov and Ekaterina S. Keyn and Vladislav Yu. Shuvalov and Anastasia S. Kostyuchenko},
title = {A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines},
journal = {Synthesis},
year = {2024},
volume = {56},
publisher = {Georg Thieme Verlag KG},
month = {may},
url = {http://www.thieme-connect.de/DOI/DOI?10.1055/a-2323-0770},
number = {13},
pages = {2100--2108},
doi = {10.1055/a-2323-0770}
}
Cite this
MLA
Copy
Shatsauskas, Anton L., et al. “A synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: the Pictet–Spengler reaction vs a rearrangement of 4-phenyl[1,3]oxazolo[4,5-c]quinolines.” Synthesis, vol. 56, no. 13, May. 2024, pp. 2100-2108. http://www.thieme-connect.de/DOI/DOI?10.1055/a-2323-0770.