American Chemical Society (ACS)
Organic Letters
,  volume 24 ,  issue 36 ,  pages 6582-6587

Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity

Publication type: Journal Article
Publication date: 2022-09-07
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Counterintuitively, the low basicity of the NH2 group in hydrazides makes them preferred nucleophiles for the synthesis of the N-substituted azaozonides in acid-catalyzed three-component condensation with 1,5-diketones and H2O2. In the case of more basic N sources, e.g., hydrazine and primary amines, such condensation does not occur under these reaction conditions. The method can be applied to a wide range of hydrazides and affords the target bicyclic azaozonides in 27-86% yields.
Found 
Found 
6 citations
Yaremenko Ivan
PhD in Chemistry
60 publications,  1 567 citations,  5 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
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Radulov Peter
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Yaremenko I. A. et al. Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity // Organic Letters. 2022. Vol. 24. No. 36. pp. 6582-6587.
GOST all authors (up to 50) Copy
Yaremenko I. A., Belyakova Y. Yu., Radulov P. S., Novikov R. G., Medvedev M. G., Krivoshchapov N. V., Alabugin I. V., Terent’ev A. O. Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity // Organic Letters. 2022. Vol. 24. No. 36. pp. 6582-6587.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.2c02551
UR - https://doi.org/10.1021/acs.orglett.2c02551
TI - Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity
T2 - Organic Letters
AU - Yaremenko, Ivan A
AU - Belyakova, Yulia Yu
AU - Radulov, Peter S
AU - Novikov, Roman G.
AU - Medvedev, Michael G.
AU - Krivoshchapov, Nikolai V
AU - Alabugin, Igor V.
AU - Terent’ev, Alexander O.
PY - 2022
DA - 2022/09/07
PB - American Chemical Society (ACS)
SP - 6582-6587
IS - 36
VL - 24
PMID - 36070396
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Yaremenko,
author = {Ivan A Yaremenko and Yulia Yu Belyakova and Peter S Radulov and Roman G. Novikov and Michael G. Medvedev and Nikolai V Krivoshchapov and Igor V. Alabugin and Alexander O. Terent’ev},
title = {Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.orglett.2c02551},
number = {36},
pages = {6582--6587},
doi = {10.1021/acs.orglett.2c02551}
}
MLA
Cite this
MLA Copy
Yaremenko, Ivan A., et al. “Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity.” Organic Letters, vol. 24, no. 36, Sep. 2022, pp. 6582-6587. https://doi.org/10.1021/acs.orglett.2c02551.