Organic Chemistry: Current Research
Open Access

Synthesis of fused dipyranocoumarins and pyridopyranocoumarins. Biological evalution of the products

10^th European Organic Chemistry Congress

March 21-22, 2019 | Rome, Italy

Evangelia-Eirini Vlachou, Ioannis Fotopoulos, Dimitra Hadjipavlou-Litina and Konstantinos Litinas

Aristotle University of Thessaloniki, Greece

Scientific Tracks Abstracts: Organic Chem Curr Res

Abstract :

Dipetalolactone and 4-methyldipetalolactone are prepared in excellent yield by a one-pot tandem propargylation/ Claisen rearrangement/cyclization reaction of the corresponding 5,7-dihydroxycoumarins with 3-chloro-3- methylbut-1-yne in the presence of Cs2CO3 under microwave irradiation. The analogous reactions of propargyl chloride with esculetins or 5,7-dihydroxy-coumarins led to dipropargyloxy derivatives. The later by treatment with gold nanoparticles supported on TiO2 or BF3.Et2O in DMF, under microwave irradiation resulted in very good to excellent yield to the corresponding fused dipyranocoumarins. The reactions of esculetins with 3-chloro-3-methylbut- 1-yne gave mainly exo-methylene fused dioxino[g]coumarins. The reactions of 6-amino-7-hydroxycoumarins and 7-amino-6-hydroxycoumarins with propargyl bromide and 3-chloro-3-methylbut-1-yne in the presence of Cs2CO3 under microwave irradiation led to dipropargyl derivatives. The latter by treatment with gold nanoparticles supported on TiO2 or BF3.Et2O in DMF, under microwave irradiation resulted to the corresponding fused pyridopyranocoumarins. The new compounds were tested in vitro for their antioxidant and antiinflammatory activities.

Biography :

Evangelia-Eirini Vlachou has completed her MSc at the age of 25 years from Aristotle University, Department of Chemistry, in Organic Synthesis. Now she continues her studies as a PhD student at the same field. She has participated in many conferences and she has published two papers in Journal of Heterocyclic Chemistry and in Bioorganic Chemistry until now.