Catalytic [4+1]-annulation of thioamides with carbenoid precursors
Vladimir G Ilkin
1
,
Irina A Utepova
3
,
Pavel A. Slepukhin
3, 4
,
Andrey A Tumashov
3, 4
,
Wim Dehaen
5
,
Publication type: Journal Article
Publication date: 2024-02-20
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Organic Chemistry
Abstract
A Rh(II)/Cu(I)-catalyzed [4 + 1]-annulation of readily available thioamides with 1-sulfonyl-1,2,3-triazoles and diazoamides was developed, delivering a general approach toward highly substituted dihydrothiophenes. A series of dihydrothiophenes having a wide diversity of functional groups, including spirocyclic, dispirocyclic and bicyclic derivatives were synthesized in high yields and good diastereoselectivity. The diastereoselectivity for the reaction of 2-(morpholino-4-carbonothioyl)-3-phenylacrylonitrile with diazoacetamides can be switched by replacing Rh(II) with a Cu(I) catalyst. Cycloalkylidene substituted thioamides formed various regioisomers under Rh(II) or Cu(I) catalysis. Furthermore, reactions of 3-diazomethylindolin-2-one with thioamides can be performed enantioselectively with ee up to 97%.
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8
Total citations:
8
Citations from 2024:
8
(100%)
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GOST
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Ilkin V. G. et al. Catalytic [4+1]-annulation of thioamides with carbenoid precursors // Organic Chemistry Frontiers. 2024. Vol. 11. No. 13. pp. 3537-3545.
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Ilkin V. G., Filimonov V. O., Utepova I. A., Beryozkina T. V., Slepukhin P. A., Tumashov A. A., Dehaen W., Bakulev V. A. Catalytic [4+1]-annulation of thioamides with carbenoid precursors // Organic Chemistry Frontiers. 2024. Vol. 11. No. 13. pp. 3537-3545.
Cite this
RIS
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TY - JOUR
DO - 10.1039/d3qo02025h
UR - https://xlink.rsc.org/?DOI=D3QO02025H
TI - Catalytic [4+1]-annulation of thioamides with carbenoid precursors
T2 - Organic Chemistry Frontiers
AU - Ilkin, Vladimir G
AU - Filimonov, Valeriy O
AU - Utepova, Irina A
AU - Beryozkina, Tetyana V
AU - Slepukhin, Pavel A.
AU - Tumashov, Andrey A
AU - Dehaen, Wim
AU - Bakulev, Vasiliy A.
PY - 2024
DA - 2024/02/20
PB - Royal Society of Chemistry (RSC)
SP - 3537-3545
IS - 13
VL - 11
SN - 2052-4110
SN - 2052-4129
ER -
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BibTex (up to 50 authors)
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@article{2024_Ilkin,
author = {Vladimir G Ilkin and Valeriy O Filimonov and Irina A Utepova and Tetyana V Beryozkina and Pavel A. Slepukhin and Andrey A Tumashov and Wim Dehaen and Vasiliy A. Bakulev},
title = {Catalytic [4+1]-annulation of thioamides with carbenoid precursors},
journal = {Organic Chemistry Frontiers},
year = {2024},
volume = {11},
publisher = {Royal Society of Chemistry (RSC)},
month = {feb},
url = {https://xlink.rsc.org/?DOI=D3QO02025H},
number = {13},
pages = {3537--3545},
doi = {10.1039/d3qo02025h}
}
Cite this
MLA
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Ilkin, Vladimir G., et al. “Catalytic [4+1]-annulation of thioamides with carbenoid precursors.” Organic Chemistry Frontiers, vol. 11, no. 13, Feb. 2024, pp. 3537-3545. https://xlink.rsc.org/?DOI=D3QO02025H.