A general approach to the synthesis of substituted isoxazolo[4,3-c]quinolines via chalcones

A general and practical approach to the synthesis of substituted isoxazolo[4,3-c]quinolines from the substituted isoxazolines afforded by 1,3-dipolar cycloaddition between 2-nitrobenzonitrile oxide and chalcones is described. The SnCl2.2H2O-mediated reduction of the nitro group followed by intramolecular cyclization involving the amino and the keto groups in these substrates furnished a mixture of isoxazolo[4,3- c]-quinolines and 3,5-dihydro-isoxazolo[4,3-c]quinoline. In contrast, the reduction of these substrates with Fe-AcOH unexpectedly yielded 3-benzoyl-4-quinolinamine derivatives.

An alternate approach to quinoline architecture via Baylis-Hillman chemistry: SnCl2-mediated tandem reaction toward synthesis of 4-(substituted vinyl)-quinolines

An alternate approach to densely substituted quinolines from the products of SN2 nucleophilic substitution reaction between the acetyl derivatives of the Baylis-Hillman adducts obtained from 2-nitrobenzaldehydes and the carbonyl group containing carbon nucleophiles is described. Treatment of these compounds with SnCl2, trigger a tandem reaction wherein reduction of the nitro group is followed by a remarkably regioselective intramolecular cyclization and subsequent dehydrogenation to afford 4-(substituted vinyl)-quinolines.