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The Synthesis and Reactions of 1‐(2‐Propynyl)pyidinium Salts
Author(s) -
Katritzky Alan R.,
Schwarz Otto A.,
Rubio Olga,
Markees Diether G.
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670404
Subject(s) - chemistry , propynyl , pyridinium , diethylamine , pyridine , sodium methoxide , ether , medicinal chemistry , enol , hydrolysis , hydrochloride , organic chemistry , methanol , catalysis
The synthesis of 1‐(2‐propynyl)pyridinium salts 3 described. Compounds 3 react with a second pyridine molecule, in the presence of the corresponding hydrochloride, to form products of type 4 , Certain bases cause the 1‐(2‐propynyl)pyridinium salts 3 to rearrange into 1‐propadienylpyridinium salts. 5 . Diethylamine converts compounds 3 into 1‐acetonylpyridinium salts 8 . Moreover, treatment of 3 or 5 with sodium methoxide gives enol ether sof type 9, which can be hydrolyzed to teh ketones 8 . Addition of bromine to some of teh unsaturated compounds is also reported.