Novel heterocycles derived from 3-acyloxy- and 3-acetamidoquinuclidines

Article abstract of DOI:10.1002/jhet.5570310636

New quinuclidine derivatives with 3-spiro annelated oxathioline, furanone, and pyrrolinone heterocycles have been synthesized from 3-mesyloxy-, 3-acetoxy-, and 3-acetamidoquinuclidine-3-carbonitrile, respectively, by treatment with base. Treatment of 3-acetamidoquinuclidine-3-carbonitrile (3) with potassium hydride resulted in decyanation whereas alkyllithium reagents attacked the cyano group in 3 to produce the corresponding imines. Oxidative cyclization of the N-benzylated derivative of 3 with palladium acetate gave the tetracyclic compound 5-acetyl-1,4-ethano-1,2,3,4,5,6-hexahydrobenzo[c]-1,5-naphthyridine.