American Chemical Society (ACS)
Journal of Organic Chemistry
,  volume 88 ,  issue 19 ,  pages 13782-13795

Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame?

Publication type: Journal Article
Publication date: 2023-09-19
American Chemical Society (ACS)
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Relief of stereoelectronic frustration drives the acid-catalyzed three-component condensation of β,δ'-triketones with hydrazides and H2O2 to the direction where both nucleophiles and all three electrophilic carbons are involved in the formation of a tricyclic sp3-rich ring system that includes four heteroatoms. The otherwise inaccessible tricyclic N-substituted aminoperoxides are prepared rapidly and selectively from relatively simple substrates in good to high yields.
Found 
Found 
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GOST Copy
Yaremenko I. A. et al. Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame? // Journal of Organic Chemistry. 2023. Vol. 88. No. 19. pp. 13782-13795.
GOST all authors (up to 50) Copy
Yaremenko I. A., Belyakova Y. Yu., Radulov P. S., Medvedev M. G., Krivoshchapov N. V., Alabugin I. V., Terent'ev A. O. Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame? // Journal of Organic Chemistry. 2023. Vol. 88. No. 19. pp. 13782-13795.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.joc.3c01415
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c01415
TI - Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame?
T2 - Journal of Organic Chemistry
AU - Yaremenko, Ivan A
AU - Belyakova, Yulia Yu
AU - Radulov, Peter S
AU - Medvedev, Michael G.
AU - Krivoshchapov, Nikolai V
AU - Alabugin, Igor V.
AU - Terent'ev, Alexander O.
PY - 2023
DA - 2023/09/19
PB - American Chemical Society (ACS)
SP - 13782-13795
IS - 19
VL - 88
PMID - 37724879
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Yaremenko,
author = {Ivan A Yaremenko and Yulia Yu Belyakova and Peter S Radulov and Michael G. Medvedev and Nikolai V Krivoshchapov and Igor V. Alabugin and Alexander O. Terent'ev},
title = {Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame?},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c01415},
number = {19},
pages = {13782--13795},
doi = {10.1021/acs.joc.3c01415}
}
MLA
Cite this
MLA Copy
Yaremenko, Ivan A., et al. “Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame?.” Journal of Organic Chemistry, vol. 88, no. 19, Sep. 2023, pp. 13782-13795. https://pubs.acs.org/doi/10.1021/acs.joc.3c01415.