One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system
Publication type: Journal Article
Publication date: 2023-04-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
Phenanthridine readily undergoes one-pot N-acylvinylation/C-phosphorylation in the terminal acetylenic ketone—secondary phosphine oxide system at room temperature (acetonitrile, 48–72 h) in the absence of a catalyst to stereoselectively form (E)-N-acylvinyl-6-diorganylphosphoryl-5,6-dihydrophenanthridines in up to 88% preparative yield. Under similar conditions, secondary phosphine sulfides form a difficult-to-separate mixture of N-vinylation/C-phosphorylation products and adducts of phosphine sulfides with acetylenic ketones, while bis(2-phenylethyl)phosphine selenide gives only an adduct with acetylenic ketone in 78% yield.
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Total citations:
8
Citations from 2025:
1
(12.5%)
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Volkov P. A. et al. One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system // Russian Chemical Bulletin. 2023. Vol. 72. No. 4. pp. 955-959.
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Volkov P. A., Khrapova K. O., A. A. T., Albanov A. I., Trofimov B. A. One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system // Russian Chemical Bulletin. 2023. Vol. 72. No. 4. pp. 955-959.
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TY - JOUR
DO - 10.1007/s11172-023-3859-5
UR - https://doi.org/10.1007/s11172-023-3859-5
TI - One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system
T2 - Russian Chemical Bulletin
AU - Volkov, P. A.
AU - Khrapova, K O
AU - A. A., Telezhkin
AU - Albanov, A I
AU - Trofimov, B. A.
PY - 2023
DA - 2023/04/01
PB - Springer Nature
SP - 955-959
IS - 4
VL - 72
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2023_Volkov,
author = {P. A. Volkov and K O Khrapova and Telezhkin A. A. and A I Albanov and B. A. Trofimov},
title = {One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system},
journal = {Russian Chemical Bulletin},
year = {2023},
volume = {72},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s11172-023-3859-5},
number = {4},
pages = {955--959},
doi = {10.1007/s11172-023-3859-5}
}
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MLA
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Volkov, P. A., et al. “One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system.” Russian Chemical Bulletin, vol. 72, no. 4, Apr. 2023, pp. 955-959. https://doi.org/10.1007/s11172-023-3859-5.