title: Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides.
abstract: On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.
authors.affiliation: School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
authors.forename: Jemma
authors.initials: J
authors.lastname: Senczyszyn
authors.forename: Heloise
authors.initials: H
authors.lastname: Brice
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
mesh_terms: D000215:Acylation; D002121:Calcium Channel Blockers; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009536:Niacinamide / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002121:Calcium Channel Blockers; D004095:Dihydropyridines; D013141:Spiro Compounds; D009536:Niacinamide; C027681:isonicotinamide