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

Elena Yu Schmidt; Nadezhda V Semenova; Elena V Ivanova; Inna V Tatarinova; Igor' A Ushakov; Alexander V Vashchenko; Boris A Trofimov

doi:10.1039/c9cc00315k

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

Chem Commun (Camb). 2019 Feb 26;55(18):2632-2635. doi: 10.1039/c9cc00315k.

Authors

Elena Yu Schmidt¹, Nadezhda V Semenova, Elena V Ivanova, Inna V Tatarinova, Igor' A Ushakov, Alexander V Vashchenko, Boris A Trofimov

Affiliation

¹ A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation. boris_trofimov@irioch.irk.ru.

PMID: 30742185
DOI: 10.1039/c9cc00315k

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.