Synthesis of pyrylium salts and heterocyclic nitrogen bases from cycloalkenylacetic acid esters
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2-Alkyl-6-methoxy-3,4-tetramethylene- and 3,4-pentamethylenepyrylium perchlorates were obtained by acylation of cycloalkenylacetic acid esters with aliphatic acid anhydrides. 2-Methyl-6-methoxy[2,3-c]cholestanopyrylium perchlorate was similarly synthesized. 2-Alkyl-3,4-tetramethylene-6-pyridones were isolated by treatment of 2-alkyl-6-methoxy-3,4-tetramethylene-pyrylium perchlorates with excess concentrated ammonium hydroxide. 2-Methyl-3,4-pentamethylene-6-aminopyridine was obtained by the action of excess concentrated ammonium hydroxide on 2-methyl-6-methoxy-3,4-pentamethylenepyrylium perchlorate.
KeywordsNitrogen Ammonium Ester Hydroxide Organic Chemistry
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