Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1983-05-13
1984-10-09
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549403, 549416, C07D30934, C07D31130
Patent
active
044763131
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, an 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-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: 3617268 (1971-11-01), Murakami et al.
patent: 3896112 (1975-07-01), Kubota et al.
Huenig et al., Chemical Abstracts, vol. 82 (1975) 4099e.
Potts et al., Jacs. vol. 103 (1981), pp. 3585-3586.
Raymond Richard L.
Rensselaer Polytechnic Institute
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