Sm(III)nitrate-catalyzed one-pot synthesis of furano[3,2c]-1,2,3,4-tetrahydroquinolines and DNA photocleavage studies

The synthesis and DNA photocleavage studies of furano[3,2-c]-1,2,3,4-tetrahydroquinolines have been reported. Sm(III)nitrate was found to be an efficient for the Diels–Alder reaction of aryl amines with 2,3-dihydrofuran to offer the corresponding furano[3,2-c]-1,2,3,4-tetrahydroquinolines derivatives as a mixture of cis/trans stereoisomers in moderate yields. The aqueous solubility of acid catalyst can be recycled without significant loss of activity. The DNA photocleavage studies shows that, the cis/trans stereoisomers are good DNA cleavage mimic in terms of molecular structure.

Highlight► We have developed an convenient alternative methodology for the synthesis of furano[3,2-c]quinolines. ► Sm(III) was a good oxidising agent and importantly it act as a Lewis acid catalyst in the formation of C–C bond. ► The DNA photocleavage property of furano[3,2-c]quinolines has been investigated by agarose gel electrophoresis. ► We found that the stereoisomers are good DNA cleavage mimic in terms of molecular structure.