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

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...

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Published inOrganic letters Vol. 24; no. 36; pp. 6582 - 6587
Main Authors Yaremenko, Ivan A., Belyakova, Yulia Yu, Radulov, Peter S., Novikov, Roman A., Medvedev, Michael G., Krivoshchapov, Nikolai V., Alabugin, Igor V., Terent’ev, Alexander O.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
hydrazides
hydrazine
Lewis bases
nitrogen
Physical Sciences
Science & Technology
BASIS-SET
MOLECULAR-ORBITAL METHODS
ANTIMALARIAL
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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c02551