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Regiospecific Nucleophilic Attack at the γ‐Position of 1‐(2,6‐Dimethyl‐4‐oxo‐1,4‐dihydro‐1‐pyridyl)pyridinium Compounds; Novel Synthesis of 4‐Substituted Pyridines
Author(s) -
Katritzky Alan R.,
Beltrami Hector,
Keay James G.,
Rogers David N.,
Sammes Michael P.,
Leung Christopher W. F.,
Lee Cheuk Man
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197907922
Subject(s) - pyridinium , steric effects , chemistry , nucleophile , medicinal chemistry , position (finance) , pyridine , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , finance , economics
Syntheses of 4‐substituted pyridines (3) are always of interest. In the pyridinium ion (1) positions 2 and 6 are sterically shielded; it therefore reacts at the activated position 4 with C, N and S nuleophiles in high yields to give (2) , which is readily cleaved to (3) and (4) , or decomposes to these products.