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On the reaction of 2‐aminopyridines with alpha ‐halocarbonyl compounds
Author(s) -
Elliott Arthur J.,
Guzik Henry,
Soler Jose R.
Publication year - 1982
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.5570190636
Subject(s) - chemistry , aminopyridines , imidazopyridine , yield (engineering) , pyridine , 2 aminopyridine , phenacyl bromide , medicinal chemistry , phenacyl , adduct , nitrogen atom , organic chemistry , stereochemistry , group (periodic table) , materials science , metallurgy
The reactions of 6‐substituted‐2‐aminopyridines with bromoacetone and 3‐bromo‐2‐butanone have been investigated. In contrast to bromoacetone which gives a high yield of the imidazo[1,2‐ a ]pyridine, bromobutanone also produces significant amounts of material derived from substitution on the exocyclic nitrogen atom. These adducts, which are not a source of imidazopyridine in the reaction mixture, may be isolated and cyclised under more forcing conditions. The reactions of 2‐aminopyridine with 2‐chlorocyclohexanone and phenacyl bromide have been re‐examined and all the major products identified.