Synthesis of alkaloid-like compounds via the bridging Ritter reaction

Antiproliferative activities of alkaloid-like compounds

“…Various nitriles were used, and subsequent reactions such as reduction, reductive alkylation, and DMAD cycloaddition were used to derivatise these small molecules to heterocyclic alkaloid-like compounds. 17 …”

An alkaloid-like 3-azabicyclo[3.3.1]non-3-ene library obtained from the bridged Ritter reaction

“…6 Attack of the C-6 carbocation intermediate E by a strongly nucleophilic nitrile would eventually favour the formation of the imine-amides (+)-1 (Scheme 2), as previously reported. 7 Where the imino-amides (+)-1 are the major product, the data suggest that the transformation of E into F is controlled by the rate k 1 , which is influenced by the nucleophilicity of the nitrile, and eventually forms (+)-1 upon quenching with water. The following explains some of the other interesting outcomes that resulted from the nitrile used.…”