Details

Autor(en) / Beteiligte

• 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.

Titel

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

Ist Teil von

• Organic letters, 2022-09, Vol.24 (36), p.6582-6587

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.