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Imination of N ‐methylazinium salts by liquid ammonia/potassium permanganate
Author(s) -
Woźniak M.,
Buurman D. J.,
Van Der Plas H. C.
Publication year - 1985
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.5570220331
Subject(s) - chemistry , potassium permanganate , ammonia , adduct , liquid ammonia , demethylation , potassium , medicinal chemistry , permanganate , inorganic chemistry , methyl iodide , organic chemistry , biochemistry , gene expression , dna methylation , gene
Treatment of 1‐methylquinolinium‐, 1,4‐dimethylquinolinium‐ and 1‐methyl‐1,X‐naphthyridinium iodides (X = 5,8) with liquid ammonia/potassium permanganate leads to introduction of the imino group at C‐2 forming the 1,2‐dihydro‐2‐imino‐1‐methylquinolines and 1,2‐dihydro‐2‐imino‐1‐methyl‐1,X‐naphthyridines (X = 5,8) respectively. 1,2‐Dimethylquinolinium iodide, when subjected to treatment with liquid ammonia/potassium permanganate undergoes an oxo‐demethylation reaction, yielding 1‐methylquinol‐2‐one. The nmr‐measurements of solutions of the above‐mentioned salts in liquid ammonia clearly show the formation of a σ‐adduct, strongly suggesting that these σ‐adducts are intermediates in the imination reactions.