A Straightforward Entry to 7??Azabicyclo [2.2. 1] heptane??1??carbonitriles in the Synthesis of Novel Epibatidine Analogues

T Heugebaert, J Van Hevele, W Couck…

文献索引：Heugebaert, Thomas; Van Hevele, Joke; Couck, Wouter; Bruggeman, Vicky; Van Jeught, Sarah Der; Masschelein, Kurt; Stevens, Christian V. European Journal of Organic Chemistry, 2010 , # 6 p. 1017 - 1020

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被引用次数: 5

摘要

Abstract This paper presents the synthesis of epibatidine analogues by a straightforward one-pot method for the synthesis of 7-azabicyclo [2.2. 1] heptane-1-carbonitriles, starting from cyclohexanones bearing a leaving group at the 4-position. In situ imine formation, followed by reversible cyanide addition, allows complete conversion of 4-(mesyloxy) cyclohexanone to the bicyclic core. Elaboration of the introduced nitrile functionality and ...