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Flash vacuum pyrolysis of 3-aroylcinnolines 3 at 900 o C and 0.02Torr yielded phenanthrene and arylacetylene derivatives as the major products beside anthracene and diarylacetylene derivatives as minor products. Also, FVP of 3-(2-thienoyl)-cinnoline gave three isomeric naphthothiophenes, phenyl-2-thienylacetylene and phenylacetylene. On the other hand, 3-(2-furoyl)-cinoline gave dibenzofuran...
An efficient synthesis of 3-aroylcinnolines starting from the appropriate aryl methyl ketones is described. The latter were converted in two steps to the corresponding 3-oxo-3-aryl-2-arylhydrazonopropanals, which upon acid catalyzed cyclization in conc. sulfuric acid or polyphosphoric acid (PPA) led to the corresponding 3-aroylcinnolines.
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