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Article info. : 2005; 2(4) (pp 244~337)
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Synthesis of 6-Acylmethylphenanthridine Enaminones
H. Loghmani-Khouzania,*, R. Gawineckib,
M.M. Sadeghia, H. Mehrabia and B. Osmialowskib
aDepartment of Chemistry, Faculty of Sciences,
University of Isfahan, 81746-73441 IR Iran
bDepartment of Chemistry, Technical and Agricultural
University, Seminaryjna 3
PL-85-326 Bydgoszcz, Poland
(Received 12 July 2005, Accepted 25 September 2005)
A series of 6-acylmethylphenanthridine derivatives were
synthesized by reaction of aliphatic and aromatic esters with
6-methylphenanthridine in the presence of phenyllithium. Enaminone form of the
obtained compounds was investigated by spectroscopic methods. The results
revealed that the presence of aromatic rings on 3- and 4-position of
2-acylmethylquinolines (6-acylmethylphenanthridines) is the most important
factor for the preference of the enaminone form b. It was found that the
intramolecular hydrogen bonding is the only factor that can damage aromaticity
of the phenanthridine moiety.
Keywords: Phenanthridine; Enaminone, 2-Ketomethylquinolines, Tautomerism,
Hydrogen bonding, Aromaticity
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