A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters
Тип публикации: Journal Article
Дата публикации: 2021-07-08
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
34236865
Organic Chemistry
Краткое описание
A high yield synthesis of 2-amino-4-pyrrolin-3-ones including 4-pyrrolin-3-one-based amino esters by the NBS- or TfCl-mediated reaction of 3-hydroxypyrroles with amines has been developed. The reaction of 3-hydroxypyrroles with triflyl chloride in the absence of amine affords 2,2'-bi(4-pyrrolin-3-ones) in excellent yields and diastereoselectivity. The relative configuration of stereocenters in these compounds can be changed from (2RS,2'RS) to (2RS,2'SR) by the action of NaH in THF, while the reverse stereoisomerization occurs in the presence of 2,5-lutidine in MeCN. Bi(4-pyrrolin-3-ones) also can be converted to 2-amino-4-pyrrolin-3-ones in excellent yields. Bi(4-pyrrolin-3-ones) and 2-amino-4-pyrrolin-3-ones were evaluated for their antiproliferative activity toward four human tumor cell lines.
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Golubev A. A. et al. A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters // Journal of Organic Chemistry. 2021. Vol. 86. No. 15. pp. 10368-10379.
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Golubev A. A., Agafonova A. V., Smetanin I. A., Rostovskii N. V., Khlebnikov A. F., Bunev A. S., Novikov M. S. A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters // Journal of Organic Chemistry. 2021. Vol. 86. No. 15. pp. 10368-10379.
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TY - JOUR
DO - 10.1021/acs.joc.1c01070
UR - https://pubs.acs.org/doi/10.1021/acs.joc.1c01070
TI - A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters
T2 - Journal of Organic Chemistry
AU - Golubev, Artem A
AU - Agafonova, Anastasiya V
AU - Smetanin, Ilia A
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Bunev, Alexander S.
AU - Novikov, Mikhail S.
PY - 2021
DA - 2021/07/08
PB - American Chemical Society (ACS)
SP - 10368-10379
IS - 15
VL - 86
PMID - 34236865
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Golubev,
author = {Artem A Golubev and Anastasiya V Agafonova and Ilia A Smetanin and Nikolai V Rostovskii and Alexander F Khlebnikov and Alexander S. Bunev and Mikhail S. Novikov},
title = {A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.1c01070},
number = {15},
pages = {10368--10379},
doi = {10.1021/acs.joc.1c01070}
}
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Golubev, Artem A., et al. “A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters.” Journal of Organic Chemistry, vol. 86, no. 15, Jul. 2021, pp. 10368-10379. https://pubs.acs.org/doi/10.1021/acs.joc.1c01070.