Abstract
Condensation of 9,10-phenanthrenequinone with 2-furaldehyde and 2-thiophenecarbaldehyde in glacial acetic acid in the presence of ammonium acetate gave 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles which were converted into the corresponding 1-methyl derivatives. The furan and thiophene rings in the products lose their acidophobic properties. Depending on the conditions, electrophilic substitution reactions in 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles occur both at the furan (thiophene) and phenanthrene moieties.
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Pechkin, A.A., El'chaninov, M.M. & Stoyanov, V.M. Synthesis and Properties of 2-(2-Furyl)- and 2-(2-Thienyl)-1-methylphenanthro[9,10-d]imidazoles. Russian Journal of Organic Chemistry 38, 726–730 (2002). https://doi.org/10.1023/A:1019623408687
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DOI: https://doi.org/10.1023/A:1019623408687