The Synthesis and Reactions of 1‐(2‐Propynyl)pyidinium Salts | Zendy

Katritzky Alan R. | Zendy; Schwarz Otto A. | Zendy; Rubio Olga | Zendy; Markees Diether G. | Zendy

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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.

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