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Nucleophilic displacements of N ‐aryl and heteroaryl groups. Part 8 . Intermolecular reactions of N ‐aryl‐pyridinium, ‐quinolinium, and ‐acridinium salts with nucleophiles
Author(s) -
Katritzky Alan R.,
Wittmann Dieter K.,
Chen JenLuan,
Marson Charles M.,
Ossana Andrea
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230340
Subject(s) - chemistry , nucleophile , pyridinium , aryl , deprotonation , ring (chemistry) , pyridine , medicinal chemistry , pyrrole , stereochemistry , organic chemistry , ion , catalysis , alkyl
Abstract N ‐Aryl‐mono‐, ‐tri‐ and ‐pentacyclic pyridinium cations react with S ‐ and C‐nucleophiles to give: (i) simple addition of hydride at the α‐ring position, (ii) nucleophilic addition of thiophenoxide at the γ‐ring position, (iii) deprotonation at the 6‐position of a 5,6‐dihydroquinolinium ring followed by prototropic shift to give a 1,2‐dihydroquinoline derivative, (iv) ring contraction of a pyridine to a pyrrole ring, and (v) nucleophilic displacement of the N ‐aryl group.