Open Access
Molecules, volume 25, issue 22, pages 5379
Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles
Marina A. Vinokurova
1
,
Pavel A. Kumandin
1
,
Natalia L Merkulova
1
,
Roman A Novikov
3
,
Kirill B. Polyanskii
1
,
4
Laboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguara, Km 2 vía refugio, Piedecuesta A.A. 681011, Colombia
|
Publication type: Journal Article
Publication date: 2020-11-17
PubMed ID:
33213018
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
The ring rearrangement metathesis (RRM) of a trans-cis diastereomer mixture of methyl 3-allyl-3a,6-epoxyisoindole-7-carboxylates derived from cheap, accessible and renewable furan-based precursors in the presence of a new class of Hoveyda–Grubbs-type catalysts, comprising an N→Ru coordinate bond in a six-membered ring, results in the difficult-to-obtain natural product-like cyclopenta[b]furo[2,3-c]pyrroles. In this process, only one diastereomer with a trans-arrangement of the 3-allyl fragment relative to the 3a,6-epoxy bridge enters into the rearrangement, while the cis-isomers polymerize almost completely under the same conditions. The tested catalysts are active in the temperature range from 60 to 120 °C at a concentration of 0.5 mol % and provide better yields of the target tricycles compared to the most popular commercially available second-generation Hoveyda–Grubbs catalyst. The diastereoselectivity of the intramolecular Diels–Alder reaction furan (IMDAF) reaction between starting 1-(furan-2-yl)but-3-en-1-amines and maleic anhydride, leading to 3a,6-epoxyisoindole-7-carboxylates, was studied as well.
Top-30
Citations by journals
|
1
|
|
|
Molecules
1 publication, 12.5%
|
|
|
Asian Journal of Organic Chemistry
1 publication, 12.5%
|
|
|
Journal of Organic Chemistry
1 publication, 12.5%
|
|
|
Reaction Kinetics, Mechanisms and Catalysis
1 publication, 12.5%
|
|
|
European Journal of Organic Chemistry
1 publication, 12.5%
|
|
|
Acta Crystallographica Section E: Crystallographic Communications
1 publication, 12.5%
|
|
|
SynOpen
1 publication, 12.5%
|
|
|
Russian Chemical Reviews
1 publication, 12.5%
|
|
|
1
|
Citations by publishers
|
1
2
|
|
|
Wiley
2 publications, 25%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 12.5%
|
|
|
American Chemical Society (ACS)
1 publication, 12.5%
|
|
|
Springer Nature
1 publication, 12.5%
|
|
|
International Union of Crystallography (IUCr)
1 publication, 12.5%
|
|
|
Thieme
1 publication, 12.5%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 12.5%
|
|
|
1
2
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2021,2022,2023,2024],"ids":[0,0,0,0],"codes":[0,0,0,0],"imageUrls":["","","",""],"datasets":[{"label":"Citations number","data":[2,2,2,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["25","25","25","25"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Molecules","Asian Journal of Organic Chemistry","Journal of Organic Chemistry","Reaction Kinetics, Mechanisms and Catalysis","European Journal of Organic Chemistry","Acta Crystallographica Section E: Crystallographic Communications","SynOpen","Russian Chemical Reviews"],"ids":[1770,9409,8697,8366,19472,7164,25294,23802],"codes":[0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/xG3oC19920mmFVqkoVEGKGaMCeoalzyvWxPkVox5_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[12.5,12.5,12.5,12.5,12.5,12.5,12.5,12.5],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","Multidisciplinary Digital Publishing Institute (MDPI)","American Chemical Society (ACS)","Springer Nature","International Union of Crystallography (IUCr)","Thieme","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[11,202,40,8,730,135,9422],"codes":[0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/xG3oC19920mmFVqkoVEGKGaMCeoalzyvWxPkVox5_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[25,12.5,12.5,12.5,12.5,12.5,12.5],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0],"percentage":["0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,1,1],"percentage":["0","0","12.5","12.5"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,1,1,0],"percentage":["12.5","12.5","12.5","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,1,0,1],"percentage":["12.5","12.5","0","12.5"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0],"percentage":["0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,1,0],"percentage":["0","0","12.5","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,0],"percentage":["0","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,2,0,0],"percentage":["12.5","25","0","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,0,0,1],"percentage":["12.5","0","0","12.5"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,1,1],"percentage":["0","0","12.5","12.5"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Antonova A. S. et al. Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles // Molecules. 2020. Vol. 25. No. 22. p. 5379.
GOST all authors (up to 50)
Copy
Antonova A. S., Vinokurova M. A., Kumandin P. A., Merkulova N. L., Sinelshchikova A., Grigoriev M. S., Novikov R. A., Kouznetsov V. V., Polyanskii K. B., Zubkov F. I. Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles // Molecules. 2020. Vol. 25. No. 22. p. 5379.
Cite this
RIS
Copy
TY - JOUR
DO - 10.3390/molecules25225379
UR - https://doi.org/10.3390/molecules25225379
TI - Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles
T2 - Molecules
AU - Antonova, Alexandra S
AU - Vinokurova, Marina A.
AU - Kumandin, Pavel A.
AU - Merkulova, Natalia L
AU - Novikov, Roman A
AU - Polyanskii, Kirill B.
AU - Sinelshchikova, Anna
AU - Grigoriev, Mikhail S.
AU - Kouznetsov, Vladimir V.
AU - Zubkov, Fedor I.
PY - 2020
DA - 2020/11/17 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 5379
IS - 22
VL - 25
PMID - 33213018
SN - 1420-3049
SN - 1420-3049
ER -
Cite this
BibTex
Copy
@article{2020_Antonova,
author = {Alexandra S Antonova and Marina A. Vinokurova and Pavel A. Kumandin and Natalia L Merkulova and Roman A Novikov and Kirill B. Polyanskii and Anna Sinelshchikova and Mikhail S. Grigoriev and Vladimir V. Kouznetsov and Fedor I. Zubkov},
title = {Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles},
journal = {Molecules},
year = {2020},
volume = {25},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {nov},
url = {https://doi.org/10.3390/molecules25225379},
number = {22},
pages = {5379},
doi = {10.3390/molecules25225379}
}
Cite this
MLA
Copy
Antonova, Alexandra S., et al. “Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles.” Molecules, vol. 25, no. 22, Nov. 2020, p. 5379. https://doi.org/10.3390/molecules25225379.