KETONIC MANNICH BASES DERIVED FROM
1-(5-BROMOBENZOFURAN-2-YL)ETHAN-1-ONE#
GHEORGHE ROMAN 1*, RADU OGHINĂ 2, LIVIU SĂCĂRESCU 1 1. “Petru Poni” Institute of Macromolecular Chemistry, Department of Inorganic Polymers, 41A Aleea Gr. Ghica Vodă, 700487 Iaşi, Romania
2. ROMTEC S.R.L., 58A Bd. Poitiers, 700680 Iaşi, Romania
*Corresponding author: gheorghe.roman@icmpp.ro
1-(5-Bromobenzofuran-2-yl)ethan-1-one has been employed as substrate in a direct Mannich reaction with common secondary amines to generate several β-aminoketones hydrochlorides. Alkylation of S- and N-nucleophiles (4-chlorothiophenol, piperazine, sulfanilamide, 3,5-dimethylpyrazole) with the dimethylamine-containing β-aminoketone derived from the aforementioned substrate has also been investigated. Reaction of the same ketonic Mannich base with phenylhydrazine afforded the corresponding 1,3-disubstituted pyrazoline, whose UV-Vis absorption has been measured in dimethylsulfoxide, toluene and chloroform at room temperature to give similar spectra having a maximum at approximately 390 nm. The fluorescence spectrum of this pyrazoline in toluene is more intense and blue-shifted compared to its emission spectrum in dimethylsulfoxide.
