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Paper | Regular issue | Vol 91, No. 1, 2015, pp.49-63
Published online, 7th January, 2015
DOI: 10.3987/COM-14-13104
■ Cyclohexane-Fused Pyridine Derivatives with Photophysical Properties: Synthesis by “Three-Component” Domino Reaction and Structural Optimization by DFT Calculations

Jianqiang Wang, Ziping Li, Xinzhi Wang, Yixin Zhou, and Cheng Guo*

*College of Science, Nanjing Tech University, Nanjing 211816, China

Abstract

An environment-friendly and highly efficient method for the preparation of 2-amino-4-phenyl-3-cyano-5,6-dihydrobenzo[h]quinoline derivatives was successfully developed via arylaldehyde, 3,4-dihydro-1(2H)- naphthalenone, malononitrile, ammonium acetate in ethanol by “three-component” domino reaction under microwave irradiation. The reaction conditions were optimized by changing microwave power, temperature and time. Their structures were characterized by ESI-MS, 1H-NMR, 13C-NMR, and IR. Their photophysical properties were detected by UV-Vis and fluorescent spectra. The results of density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations were applied to simulate spectra of the compounds, which show excellent agreement with observed spectra and provide reasonable explanation on the structures, the molecular frontier orbital, and the electronic absorption spectra.