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…

Index: 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

Full Text: HTML

Citation Number: 5

Abstract

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 ...

Related Articles:

4-Substituted Cyclohexanones. Predicting the Facial Selectivity of Nucleophilic Attacks from the Geometrical Changes on Cation-Carbonyl Complexation: An ab Initio …

[Yadav, Veejendra K.; Jeyaraj, Duraiswamy A. Journal of Organic Chemistry, 1998 , vol. 63, # 10 p. 3474 - 3477]

4-Substituted Cyclohexanones. Predicting the Facial Selectivity of Nucleophilic Attacks from the Geometrical Changes on Cation-Carbonyl Complexation: An ab Initio …

[Yadav, Veejendra K.; Jeyaraj, Duraiswamy A. Journal of Organic Chemistry, 1998 , vol. 63, # 10 p. 3474 - 3477]

4-Substituted Cyclohexanones. Predicting the Facial Selectivity of Nucleophilic Attacks from the Geometrical Changes on Cation-Carbonyl Complexation: An ab Initio …

[Yadav, Veejendra K.; Jeyaraj, Duraiswamy A. Journal of Organic Chemistry, 1998 , vol. 63, # 10 p. 3474 - 3477]

Beyond the diketopiperazine family with alternatively bridged brevianamide F analogues

[Heugebaert, Thomas S.A.; Van Overtveldt, Melissa; De Blieck, Ann; Wuyts, Benjamin; Augustijns, Patrick; Ponce-Gamez, Eugenia; Rivera, Alicia; De Groote, Dominic; Lefebvre, Romain A.; Wouters, Patrick; Meert, Theo; Devulder, Jacques; Stevens, Christian V. RSC Advances, 2014 , vol. 4, # 5 p. 2226 - 2234]

Beyond the diketopiperazine family with alternatively bridged brevianamide F analogues

[Heugebaert, Thomas S.A.; Van Overtveldt, Melissa; De Blieck, Ann; Wuyts, Benjamin; Augustijns, Patrick; Ponce-Gamez, Eugenia; Rivera, Alicia; De Groote, Dominic; Lefebvre, Romain A.; Wouters, Patrick; Meert, Theo; Devulder, Jacques; Stevens, Christian V. RSC Advances, 2014 , vol. 4, # 5 p. 2226 - 2234]

More Articles...