SYNTHESIS, CHARACTERIZATION, STEREOCHEMISTRY AND DFT STUDY OF 2-AMINO-4-BENZO[H[CHROMENE DERIVATIVES

Interaction of 4-methoxy-1-naphthol (1) with α-cyano-p-bromocinnamonitrile (2a) and ethyl α - cyano-p-bromocinnamate (2b) provided 2-amino-4-(4-bromophenyl)-6-methoxy-4Hbenzo[ h]chromene-3-carbonitrile (3a) and ethyl 2-amino-4-(4-bromophen-yl)-6-methoxy-4Hbenzo[ h]chromene-3-carboxylate (3b) respectively. Structures of these compounds were established on the basis of IR, UV, 1HNMR,13CNMR and MS data. Moreover, the stereochemistry and the DFT study are discussed. Using density functional theory geometries have been optimized at DFTB3LYP with 6- 31G* and 6-311G* level of theory, the absorption spectra has been computed by using time dependant density functional theory at TD- DFTB3LYP with 6- 31G* and 6-311G* level of theory. The HOMO-LUMO energy gap of studied systems has been discussed.