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Acetylene-based two-step diastereoselective synthesis of bridgehead dihydro-oxadiazines using ketones and hydrazine as the only reactants

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Abstract

Pharmaceutically related bridgehead dihydro-1,3,4-oxadiazines are synthesized in up to 94% yield by the acid-catalyzed diastereoselective reaction of hydrazine hydrate with 6,8-dioxabicyclo[3.2.1]octanes (6,8-DOBCOs), the products of the superbase-promoted self-organization of acetylene with ketones. The synthesis covers a diverse range of alkylaromatic ketones having F-, Cl-, Br-, alkoxy-, CF3- and aryl substituents in different positions of the aromatic rings.

Graphical abstract: Acetylene-based two-step diastereoselective synthesis of bridgehead dihydro-oxadiazines using ketones and hydrazine as the only reactants

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Publication details

The article was received on 14 Jan 2019, accepted on 04 Feb 2019 and first published on 05 Feb 2019


Article type: Communication
DOI: 10.1039/C9CC00315K
Citation: Chem. Commun., 2019, Advance Article

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    Acetylene-based two-step diastereoselective synthesis of bridgehead dihydro-oxadiazines using ketones and hydrazine as the only reactants

    E. Yu. Schmidt, N. V. Semenova, E. V. Ivanova, I. V. Tatarinova, I. A. Ushakov, A. V. Vashchenko and B. A. Trofimov, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC00315K

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