Standard

A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters. / Golubev, Artem A.; Agafonova, Anastasiya V.; Smetanin, Ilia A.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Bunev, Alexander S.; Novikov, Mikhail S.

в: Journal of Organic Chemistry, Том 86, № 15, 06.08.2021, стр. 10368-10379.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Golubev, AA, Agafonova, AV, Smetanin, IA, Rostovskii, NV, Khlebnikov, AF, Bunev, AS & Novikov, MS 2021, 'A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters', Journal of Organic Chemistry, Том. 86, № 15, стр. 10368-10379. https://doi.org/10.1021/acs.joc.1c01070

APA

Golubev, A. A., Agafonova, A. V., Smetanin, I. A., Rostovskii, N. V., Khlebnikov, A. F., Bunev, A. S., & Novikov, M. S. (2021). A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters. Journal of Organic Chemistry, 86(15), 10368-10379. https://doi.org/10.1021/acs.joc.1c01070

Vancouver

Golubev AA, Agafonova AV, Smetanin IA, Rostovskii NV, Khlebnikov AF, Bunev AS и пр. A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters. Journal of Organic Chemistry. 2021 Авг. 6;86(15):10368-10379. https://doi.org/10.1021/acs.joc.1c01070

Author

Golubev, Artem A. ; Agafonova, Anastasiya V. ; Smetanin, Ilia A. ; Rostovskii, Nikolai V. ; Khlebnikov, Alexander F. ; Bunev, Alexander S. ; Novikov, Mikhail S. / A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters. в: Journal of Organic Chemistry. 2021 ; Том 86, № 15. стр. 10368-10379.

BibTeX

@article{a182c4d64a0b4b989a1be3428107f104,
title = "A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters",
abstract = "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. ",
keywords = "DIPHENYLCYCLOPROPENONE, INHIBITORS, DESIGN, DISCOIPYRROLES, CYCLOADDITION, ISOMERIZATION, CHLORINATION, ISOXAZOLES, CHLORIDE",
author = "Golubev, {Artem A.} and Agafonova, {Anastasiya V.} and Smetanin, {Ilia A.} and Rostovskii, {Nikolai V.} and Khlebnikov, {Alexander F.} and Bunev, {Alexander S.} and Novikov, {Mikhail S.}",
note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",
year = "2021",
month = aug,
day = "6",
doi = "10.1021/acs.joc.1c01070",
language = "English",
volume = "86",
pages = "10368--10379",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "15",

}

RIS

TY - JOUR

T1 - A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters

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.

N1 - Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/8/6

Y1 - 2021/8/6

N2 - 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.

AB - 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.

KW - DIPHENYLCYCLOPROPENONE

KW - INHIBITORS

KW - DESIGN

KW - DISCOIPYRROLES

KW - CYCLOADDITION

KW - ISOMERIZATION

KW - CHLORINATION

KW - ISOXAZOLES

KW - CHLORIDE

UR - http://www.scopus.com/inward/record.url?scp=85110957432&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/eae1688f-23f8-3afa-8436-d867a29eff4a/

U2 - 10.1021/acs.joc.1c01070

DO - 10.1021/acs.joc.1c01070

M3 - Article

AN - SCOPUS:85110957432

VL - 86

SP - 10368

EP - 10379

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -

ID: 85009935