Study of Substituted Formylchromones-学术期刊.pdf

Substituted Formylchromones 1673 STUDY OF SUBSTITUTED FORMYLCHROMONES Hafez M. E a a a b L-SHAAER , Pavol ZAHRADNIK , Margita LACOVA and Maria MATULOVA a Department of Organic Chemistry, Komensky University, 842 15 Bratislava, The Slovak Republic b Institute of Chemistry, Slovak Academy of Sciences, 842 38 Bratislava, The Slovak Republic Received August 6, 1993 Accepted December 29, 1993 Substituted derivatives of 2- and 3-formylchromone were synthesized and studied by IR, 13C and 1H NMR spectroscopy and the AM1 quantum chemical method. Energy and electron distribution cal- culations confirm the preference of the synplanar conformation in 3-formylchromones. The calculated charges on the carbon atoms correlate well with the experimental 13C chemical shifts. Substituents bonded to the aromatic nucleus have only small effect on the electron structure of the pyrone ring. Thanks to their biological activity, chromone derivatives are the subject of considerable 1 pharmaceutical and chemical interest . In connection with prediction and preparation of biologically active compounds we synthesized some derivatives of 2- and 3-formyl- chromone. Whereas the derivatives of 3-formylchromone were prepared by methods 2 described in the literature , the hitherto used method of preparation of 2-formyl- chromones3 was modified to give better results. Conformational analysis was performed using the AM1 quantum chemical method, the electron stru