Pyrylium Salts via Electrophilic Cyclization: Applications for Novel 3-Arylisoquinoline Syntheses.

TitlePyrylium Salts via Electrophilic Cyclization: Applications for Novel 3-Arylisoquinoline Syntheses.
Publication TypeJournal Article
Year of Publication1999
AuthorsTovar, JD, Swager, TM
JournalJournal of Organic Chemistry
Volume64
Pagination6499–6504
ISSN0022-3263
Keywordsbenzopyrylium salt prepn ammonolysis, carbonyl compd ethynylphenyl cyclization, ethynylphenylcarbonyl compd cyclization, isoquinoline prepn
Abstract

O-Ethynylphenylcarbonyl compds. undergo cyclization to 2-benzopyrylium salts on treatment with acid. Treatment of these compds. with NH3 gave isoquinolines. 1-Ethoxy-2-benzopyrylium salts were partially hydrolyzed to the hydroxy analogs and 1-dimethylaminoisoquinolines were accompanied by the amino analogs. [on SciFinder(R)]

DOI10.1021/jo990810x