A novel approach to synthesis of the cinnoline ring ...



Title A novel approach to synthesis of the cinnoline ring system via organoiron(cyclopentadienyl) complexes.
Author(s) Ronald G. Sutherland, Alaa S. Abd El Aziz, Adam Piorko, Udai S. Gill, Choi Chuck Lee
Journal Journal of Heterocyclic Chemistry,
Date 1988
Volume 25
Issue 4
Start page 1107
End page 1110
Abstract An efficient synthesis of 3-mono or 3,4-disubstituted cinnolines from (o-dichlorobenzene)(cyclopentadienyl)iron hexafluorophosphate in 3 or 4 steps is reported. o-Chlorophenylalkyl or alkylaryl ketone complexes obtained from the o-dichlorobenzene complex upon treatment with enolate anions, react with hydrazine forming 3-mono or 3,4-disubstituted 1,4-dihydrocinnoline complexes. Treating the latter with NaNH2 forms cinnolines, i.e., 3-methyl-, 3-phenyl- and 3,4-dimethylcinnoline, via an aromatization-demetalation reaction. The influence of substituents bonded to the C atom adjacent to the complexed benzene ring in o-chlorophenylalkyl or -alkylaryl ketone prior to cyclization on the cyclization reaction is discussed.
DOI 10.1002/jhet.5570250412

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