Effect of Microwave Irradiation on the Condensation of 6-Substituted 3-Formylchromones with Some Five-membered Heterocyclic Compounds.docVIP

Molecules 2000, 5, 167-178 molecules ISSN 1420-3049 Effect of Microwave Irradiation on the Condensation of 6-Substituted 3-Formylchromones with Some Five-membered Heterocyclic Compounds Margita Lacova1*, Renata Gasparova1, Dusan Loos1*, Tibor Liptay2 and Nada Pronayova2 1 Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina CH-2, SK-842 15 Bratislava, Slovak Republic Tel.: +421 7 Fax: +421 7 E-mail: lacova@fns.uniba.sk and loos@fns.uniba.sk 2 Central Laboratories, Faculty of Chemical Technology, Slovak University of Technology, SK-812 37 Bratislava, Slovak Republic Received: 14 November 1999 / Accepted: 31 December 1999 / Published: 19 February 2000 Abstract: Different types of 3-substituted 4H-4-oxobenzopyrans were prepared by micro- wave irradiation as well as by a classical method. The beneficial effect of microwave irra- diation on the aldol condensation of 3-formylchromones with 2-imino-1-methyl- imidazolidine-4-one (creatinine), 2-thioxoimidazolidine-4-one (thiohydantoin) and 2-ethyl- 2-thioxothiazolidin-4-one (3-ethylrhodanine) in different reaction media is described. Our results show that the effect of microwave irradiation on the reactions studied was a shorten- ing of the reaction times and a smooth increase in the yields. The subsequent reactions of the product with some nucleophiles are discussed. The structure of the products was proven by elemental analysis, IR and NMR spectra. Keywords: Creatinine, thiohydantoin, rhodanine, carbamoic acids, guanidine derivatives, 1 13 Diels - Alder reaction, IR, H NMR, C NMR. Introduction This study is a continuation of our earlier publications [1-7], in which we described the theoretical, spectral and biological properties of newly synthesized chromone and chromanone derivatives. The ? 2000 by MDPI (). Reproduction is permitted for noncommercial purposes.