Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]-undecanes: access to 3-aza-6,8 dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2007

Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]-undecanes: access to 3-aza-6,8 dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks.

Résumé

Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection–spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one 18 or to the oxazinone 32 in good yields.

Domaines

Chimie organique
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Dates et versions

hal-00186417 , version 1 (09-11-2007)

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Marlène Goubert, Loic Toupet, Marie-Eve Sinibaldi, Isabelle Canet. Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]-undecanes: access to 3-aza-6,8 dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks.. Tetrahedron, 2007, 63, pp.8255-8266. ⟨10.1016/j.tet.2007.05.109⟩. ⟨hal-00186417⟩
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