Synthesis, volume 50, issue 24, pages 4897-4904
Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [ e ]-Fused 1 H -Pyrrole-2,3-diones
Publication type: Journal Article
Publication date: 2018-08-20
Catalysis
Organic Chemistry
Abstract
A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intramolecular cyclization reaction are predominantly formed under catalyst-free and solvent-free conditions. The proposed strategy provides facile access to pharmaceutically interesting pyrrole-based polyheterocycles.
Citations by journals
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2
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Tetrahedron Letters
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Tetrahedron Letters
2 publications, 40%
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Russian Journal of Organic Chemistry
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Russian Journal of Organic Chemistry
2 publications, 40%
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Beilstein Journal of Organic Chemistry
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Beilstein Journal of Organic Chemistry
1 publication, 20%
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1
2
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Citations by publishers
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1
2
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Elsevier
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Elsevier
2 publications, 40%
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Pleiades Publishing
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Pleiades Publishing
2 publications, 40%
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Beilstein-Institut
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Beilstein-Institut
1 publication, 20%
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1
2
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Khramtsova E. E., Kasatkina S. O., Maslivets A. N. Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [ e ]-Fused 1 H -Pyrrole-2,3-diones // Synthesis. 2018. Vol. 50. No. 24. pp. 4897-4904.
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Khramtsova E. E., Kasatkina S. O., Maslivets A. N. Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [ e ]-Fused 1 H -Pyrrole-2,3-diones // Synthesis. 2018. Vol. 50. No. 24. pp. 4897-4904.
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TY - JOUR
DO - 10.1055/s-0037-1610647
UR - https://doi.org/10.1055%2Fs-0037-1610647
TI - Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [ e ]-Fused 1 H -Pyrrole-2,3-diones
T2 - Synthesis
AU - Khramtsova, Ekaterina E
AU - Kasatkina, Svetlana O.
AU - Maslivets, Andrey N
PY - 2018
DA - 2018/08/20 00:00:00
PB - Thieme
SP - 4897-4904
IS - 24
VL - 50
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2018_Khramtsova,
author = {Ekaterina E Khramtsova and Svetlana O. Kasatkina and Andrey N Maslivets},
title = {Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [ e ]-Fused 1 H -Pyrrole-2,3-diones},
journal = {Synthesis},
year = {2018},
volume = {50},
publisher = {Thieme},
month = {aug},
url = {https://doi.org/10.1055%2Fs-0037-1610647},
number = {24},
pages = {4897--4904},
doi = {10.1055/s-0037-1610647}
}
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Khramtsova, Ekaterina E., et al. “Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [ e ]-Fused 1 H -Pyrrole-2,3-diones.” Synthesis, vol. 50, no. 24, Aug. 2018, pp. 4897-4904. https://doi.org/10.1055%2Fs-0037-1610647.