Cyclization of lithiated pyridine and quinoline carboxamides: synthesis of partially saturated pyrrolopyridines and spirocyclic beta-lactams.
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]
Clayden
Jonathan
J
Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK. clayden@man.ac.uk
Hamilton
Stuart D
SD
Mohammed
Rukhsana T
RT
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*
D011725:Pyridines; D011758:Pyrroles; D011804:Quinolines; D013141:Spiro Compounds; D047090:beta-Lactams; D008094:Lithium