Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity
Тип публикации: Journal Article
Дата публикации: 2022-09-07
SCImago Q1
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БС1
SJR: 1.007
CiteScore: 7.7
Impact factor: 4.7
ISSN: 15237060, 15237052
PubMed ID:
36070396
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
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.
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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.
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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.
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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 -
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@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}
}
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MLA
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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.
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