Method of making known and previously unavailable pyrylium salts

Details Method of making known and previously unavailable pyrylium salts Method of making known and previously unavailable pyrylium salts

1982-04-02

1984-05-29

Raymond, Richard

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

260239R, 546256, 546268, 549 28, 549416, 549417, C07D30932, C07F 502

Patent

active

044516592

ABSTRACT:
A method is disclosed for preparing pyrylium and thiapyrylium salts having the formula represented below (where X is O,S or Se): ##STR1## and where R.sup.1 and R.sup.2 represents a branched or unbranched alkyl radical having up to about 15 carbon atoms, an aromatic group having as substituents alkyl radicals with 1 to about 15 carbon atoms, alkoxy radicals having 1 to about 4 carbon atoms, substituted amino radicals have 1 to 2 carbon radicals containing 1 to about 4 carbon atoms, a heterocyclic group having as substitute alkyl radicals with 1 to about 15 carbon atoms, alkoxy radicals having 1 to about 4 carbon atoms and amino radicals having 1 or 2 carbon radicals containing 1 to about 4 carbons, thiophene radicals and furan radical containing a variety of substituents; R.sup.3 represents a thioalkyl radical having 1 to about 4 carbon atoms thiobenzyl, thioaryl and thiocycloalkyl, as well as thiohetaryl radicals such as thiohydridyl and related 5-and 6-membered systems; and Z.sup.- is an anionic function. The salts are prepared by condensing the methyl ketone with carbon disulfide in the presence of sodium hydride, treating the product with methyl iodide to form the .alpha.-oxoketenedithioacetal; condensing the .alpha.-oxoketenedithioacetal with another methyl ketone in the presence of two equivalents of potassium tert-butoxide to form a 1,5-enedione; and cyclizing the enedione with tetrafluoroboric acid.

REFERENCES:
patent: 4343948 (1982-08-01), Kawamura et al.

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