ChemistrySelect, volume 6, issue 24, pages 6295-6301
Reaction of Aroylpyrrolobenzothiazinetriones with Electron-Rich Dienophiles
Lystsova E A
1
,
Jasiński Ryszard
2
2
Institute of Organic Chemistry & Technology Cracow University of Technology Kraków Warszawska 24 31-155 Krakow Poland
|
Publication type: Journal Article
Publication date: 2021-06-25
General Chemistry
Abstract
The development of synthetic protocols to small molecules with a complex 3D shape is a relevant problem for modern chemists because such molecules are required by drug discovery. The Diels‐Alder reaction is a good synthetic approach to complex three‐dimensional structures. In the present paper, a reaction of aroylpyrrolobenzothiazinetriones (oxa‐dienes) with electron‐rich dienophiles is investigated in order to reach novel alkaloid‐like pyrano[4,3‐b]pyrroles fused to a 1,4‐benzothiazine‐2‐one moiety. The studied reaction was found to proceed highly regioselectively. Its stereoselectivity was dramatically dependent on the reaction solvent. The experimental results are supplemented with computational studies, which demonstrate that the studied reaction proceeds via a one‐step polar mechanism. In addition, an improved synthesis of alkaloid‐like pentacyclic 6/6/5/6/5‐ and 6/6/5/6/6‐angularly fused pyrano[4,3‐b]pyrroles via an acid‐catalyzed intramolecular cyclization of Michael adducts to hetero‐Diels‐Alder cycloadducts was discovered. The synthesized alkaloid‐like heterocycles represent an interest to pharmaceutics, since their close analogs show significant antiviral activity.
Citations by journals
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2
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Molecules
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Molecules
2 publications, 33.33%
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Beilstein Journal of Organic Chemistry
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Beilstein Journal of Organic Chemistry
2 publications, 33.33%
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Organic Letters
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Organic Letters
1 publication, 16.67%
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MolBank
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MolBank
1 publication, 16.67%
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1
2
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Citations by publishers
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1
2
3
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
3 publications, 50%
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Beilstein-Institut
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Beilstein-Institut
2 publications, 33.33%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 16.67%
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1
2
3
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Khramtsova E. E. et al. Reaction of Aroylpyrrolobenzothiazinetriones with Electron-Rich Dienophiles // ChemistrySelect. 2021. Vol. 6. No. 24. pp. 6295-6301.
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Khramtsova E. E., Lystsova E. A., Dmitriev M. V., Maslivets A. N., Jasiński R. Reaction of Aroylpyrrolobenzothiazinetriones with Electron-Rich Dienophiles // ChemistrySelect. 2021. Vol. 6. No. 24. pp. 6295-6301.
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TY - JOUR
DO - 10.1002/slct.202101990
UR - https://doi.org/10.1002%2Fslct.202101990
TI - Reaction of Aroylpyrrolobenzothiazinetriones with Electron-Rich Dienophiles
T2 - ChemistrySelect
AU - Khramtsova, Ekaterina E
AU - Lystsova, E A
AU - Dmitriev, Maksim V
AU - Maslivets, Andrey N
AU - Jasiński, Ryszard
PY - 2021
DA - 2021/06/25 00:00:00
PB - Wiley
SP - 6295-6301
IS - 24
VL - 6
SN - 2365-6549
ER -
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@article{2021_Khramtsova,
author = {Ekaterina E Khramtsova and E A Lystsova and Maksim V Dmitriev and Andrey N Maslivets and Ryszard Jasiński},
title = {Reaction of Aroylpyrrolobenzothiazinetriones with Electron-Rich Dienophiles},
journal = {ChemistrySelect},
year = {2021},
volume = {6},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002%2Fslct.202101990},
number = {24},
pages = {6295--6301},
doi = {10.1002/slct.202101990}
}
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Khramtsova, Ekaterina E., et al. “Reaction of Aroylpyrrolobenzothiazinetriones with Electron-Rich Dienophiles.” ChemistrySelect, vol. 6, no. 24, Jun. 2021, pp. 6295-6301. https://doi.org/10.1002%2Fslct.202101990.