title: Cyclization of lithiated pyridine and quinoline carboxamides: synthesis of partially saturated pyrrolopyridines and spirocyclic beta-lactams.
abstract: Lithiation of N-benzyl pyridine and quinoline carboxamides alpha to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring-containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic beta-lactams. [reaction: see text]
authors.affiliation: Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK. clayden@man.ac.uk
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
authors.forename: Stuart D
authors.initials: SD
authors.lastname: Hamilton
authors.forename: Rukhsana T
authors.initials: RT
authors.lastname: Mohammed
mesh_terms: D003500:Cyclization; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis*; D011804:Quinolines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D047090:beta-Lactams / Q000138:chemical synthesis*
chemical_list: D011725:Pyridines; D011758:Pyrroles; D011804:Quinolines; D013141:Spiro Compounds; D047090:beta-Lactams; D008094:Lithium