volume 54 issue 02 pages 506-516

Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds

Igor B Krylov
Valentina M Merkulova
Vera A. Vil’
Gennady I. Nikishin
Publication typeJournal Article
Publication date2021-09-13
scimago Q2
wos Q2
SJR0.559
CiteScore4.6
Impact factor2.3
ISSN00397881, 1437210X
Catalysis
Organic Chemistry
Abstract

The reactivity of CH-acidic and structurally related enol-containing heterocycles towards N-oxyl radicals is disclosed. Traditionally, these substrates have been considered as reactants for ionic transformations. Highly selective and efficient N-oxyl radical mediated C–O coupling of substituted barbituric or Meldrum’s acids with N-hydroxy compounds (N-hydroxyimides, hydroxamic acids, oximes, and N-hydroxybenzotriazole) was achieved using inexpensive manganese-containing salts as oxidants. Metal-free C–O coupling was demonstrated using diacetyliminoxyl as both the oxidant (hydrogen-atom acceptor) and the coupling partner.

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Terent’ev A. O. et al. Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds // Synthesis. 2021. Vol. 54. No. 02. pp. 506-516.
GOST all authors (up to 50) Copy
Terent’ev A. O., Krylov I. B., Krylov I. B., Paveliev S. A., Budnikov A. S., Segida O. O., Merkulova V. M., Vil’ V. A., Nikishin G. I. Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds // Synthesis. 2021. Vol. 54. No. 02. pp. 506-516.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/a-1643-7642
UR - https://doi.org/10.1055/a-1643-7642
TI - Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds
T2 - Synthesis
AU - Terent’ev, Alexander O.
AU - Krylov, Igor B.
AU - Krylov, Igor B
AU - Paveliev, Stanislav A
AU - Budnikov, Alexander S
AU - Segida, Oleg O
AU - Merkulova, Valentina M
AU - Vil’, Vera A.
AU - Nikishin, Gennady I.
PY - 2021
DA - 2021/09/13
PB - Georg Thieme Verlag KG
SP - 506-516
IS - 02
VL - 54
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Terent’ev,
author = {Alexander O. Terent’ev and Igor B. Krylov and Igor B Krylov and Stanislav A Paveliev and Alexander S Budnikov and Oleg O Segida and Valentina M Merkulova and Vera A. Vil’ and Gennady I. Nikishin},
title = {Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds},
journal = {Synthesis},
year = {2021},
volume = {54},
publisher = {Georg Thieme Verlag KG},
month = {sep},
url = {https://doi.org/10.1055/a-1643-7642},
number = {02},
pages = {506--516},
doi = {10.1055/a-1643-7642}
}
MLA
Cite this
MLA Copy
Terent’ev, Alexander O., et al. “Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds.” Synthesis, vol. 54, no. 02, Sep. 2021, pp. 506-516. https://doi.org/10.1055/a-1643-7642.