том 85 издание 15 страницы 10072-10082

Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones

Тип публикацииJournal Article
Дата публикации2020-07-09
scimago Q2
wos Q1
БС1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
Organic Chemistry
Краткое описание
In this work, we describe the development of the rearrangement for 7-aryl-substituted oxazolo[5,4-b]pyridines treated with aluminum chloride into synthetically hard-to-reach benzo[c][1,7]naphthyridinones. The discovered rearrangement is applied to a variety of electron-rich (hetero)arene substrates. It offers the advantages of mild conditions (90 °C temperature), fast reaction rates (<4 h), compatibility with air moisture, and the use of inexpensive commercial reagents. The proposed reaction mechanism and key elementary reaction acts were studied in detail using quantum chemical calculations. The photophysical properties of the synthesized compounds were studied by steady-state UV-vis spectroscopy.
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Shatsauskas A. L. et al. Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones // Journal of Organic Chemistry. 2020. Vol. 85. No. 15. pp. 10072-10082.
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Shatsauskas A. L., Mamonova T. E., Stasyuk A. J., Chernenko S. A., Slepukhin P. A., Kostyuchenko A. S., Fisyuk A. S. Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones // Journal of Organic Chemistry. 2020. Vol. 85. No. 15. pp. 10072-10082.
RIS |
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TY - JOUR
DO - 10.1021/acs.joc.0c01299
UR - https://doi.org/10.1021/acs.joc.0c01299
TI - Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones
T2 - Journal of Organic Chemistry
AU - Shatsauskas, Anton L.
AU - Mamonova, Tatyana E.
AU - Stasyuk, Antony J.
AU - Chernenko, Sergey A.
AU - Slepukhin, Pavel A.
AU - Kostyuchenko, Anastasia S.
AU - Fisyuk, Alexander S.
PY - 2020
DA - 2020/07/09
PB - American Chemical Society (ACS)
SP - 10072-10082
IS - 15
VL - 85
PMID - 32643932
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2020_Shatsauskas,
author = {Anton L. Shatsauskas and Tatyana E. Mamonova and Antony J. Stasyuk and Sergey A. Chernenko and Pavel A. Slepukhin and Anastasia S. Kostyuchenko and Alexander S. Fisyuk},
title = {Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.0c01299},
number = {15},
pages = {10072--10082},
doi = {10.1021/acs.joc.0c01299}
}
MLA
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Shatsauskas, Anton L., et al. “Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones.” Journal of Organic Chemistry, vol. 85, no. 15, Jul. 2020, pp. 10072-10082. https://doi.org/10.1021/acs.joc.0c01299.