Acta Chimica Slovaca (ACS) publishes papers on fundamental and applied aspects of chemistry, biochemistry, chemical technology, chemical engineering and process control, biotechnology and food technology. Welcome are also topics which include chemical aspects of materials, physical chemistry and chemical physics, analytical chemistry, macromolecular chemistry and biomedical engineering.

Novel synthesis of known carcinogen precursors

Milata Viktor *, Branislav Pavilek, Dušan Bortňák, Zuzana Svítková, Michaela Halinkovičová

Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského street 9, SK-812 37 Bratislava, Slovakia

E-mail: * viktor.milata@stuba.sk

Abstract: 5-Amino-1-methylbenzimidazole (2) prepared from 2,4-dinitrochlorobenzene in four steps is a suitable reagent for nucleophilic vinylic substitution with various enolethers (3) thus affording N-substituted enaminoesters — aminoethylene derivatives (4). Their thermal cyclocondensation reaction under the Gould-Jacobs protocol gives regioselectively angularly annelated 8-substituted imidazo[4,5-f]quinolones (5), whose mechanism of origin has been attempted. The obtained results give suitable structures for the synthesis of food-borne carcinogen IQ (1).

Keywords: enaminoesters, food-borne carcinogens, Gould-Jacobs reaction, imidazoquinoline, IQ, 1H and 13C NMR

Acta Chimica Slovaca, Vol. 17, No. 1, 2024, pp. 39—44, DOI: DOI: 10.2478/acs-2024-0005