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    STUDIA CHEMIA - Issue no. 3 / 2011  
         
  Article:   NEW 1-AZABICYCLO[3.2.2]NONANE DERIVATIVES OBTAINED BY NUCLEOPHILIC DISPLACEMENT AT CARBON C9 OF CINCHONA ALKALOIDS .

Authors:  LUMINIŢA SILAGHI-DUMITRESCU.
 
       
         
  Abstract:  Nucleophilic substitution of mesylates prepared from cinchona alkaloids, generated new 1-azabicyclo[3.2.2]nonan derivatives by cage extension rearrangement reactions which accompanied the displacement of the leaving group. Moderate yields of substituted [3.2.2]azabicyclo derivatives were obtained when water, potassium cyanide or phthalimide nucleophiles were employed. The new substituted [3.2.2]azabicyclo derivatives were further functionalized by oxidation, reduction or condensation reactions.

Keywprds: cinchona alkaloids, SN-displacement, 1-azabicyclo[3.2.2]nonane
 
         
     
         
         
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