A Straightforward Entry to 7‐Azabicyclo[2.2.1]heptane‐1‐carbonitriles in the Synthesis of Novel Epibatidine Analogues

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, al-

Redox‐Mediated Synthesis of Functionalised Graphene: A Strategy towards 2D Multifunctional Electrocatalysts for Energy Conversion Applications

“…Having synthesized precursor 11 , several experiments were carried out to construct the isoquinuclidine core, using our cyanide‐induced dynamic intramolecular cyclization reaction with acetone cyanohydrin as a hydrogen cyanide source 17. 4‐(Methanesulfonyloxymethyl)cyclohexanone ( 11 ) in dry methanol was treated with a primary amine, triethylamine, and acetone cyanohydrin in a sealed pressure vial at 110 °C for 2 d (Scheme ).…”

Ionic Liquids Based on the 7‐Azabicyclo[2.2.1]heptane Skeleton: Synthesis and Properties

“…The procedure used for the synthesis of the tosylate 6 was based on previous work by our research group25 and started from 1,4‐dioxaspiro[4.5]decan‐8‐one ( 3 ). After reduction with NaBH 4 (instead of LiAlH 4 as in the original procedure because this leads to a simpler purification) to 4 , the acetal was first deprotected with 1 mol‐% p TsOH to form 5 before tosylation26 with TsCl in pyridine.…”

“…To synthesize the azabicyclic core, a one‐pot reaction was used that had previously been developed by our group 25. Tosylate 6 and 2 equiv.…”

Straightforward Microwave‐Assisted Synthesis of 5,8‐Disubstituted 5,6,8,9‐Te­trahydro‐4H,7H‐2,5,6a,8,9a‐pentaazaphenalene‐1,3‐diones

“…[4] There is a great need for new scaffolds in medicinal chemistry in order to obtain more active, safe, reliable, orally available, and selective active pharmaceutical ingredients (APIs). [7] [a] Research Group SynBioC, Department ating one C-C and seven C-N bonds. [6] Therefore, increasing the chemical diversity in the field of heterocyclic chemistry is of great interest for the pharmaceutical industry.…”