Helicid-quinoline 2 was synthesized by using L-proline as an effective organocatalyst in one step, and a series of quinoline derivatives 3a～3c, 4 and 5a～5c were obtained from 2. Helicid-flavone derivatives 8 and 9a～9c were conveniently prepared from benzyl bromide, helicid, 2-hydroxyacetophenone, semicarbazide hydrochloride, hydroxylamine hydrochloride and methoxy amine hydrochloride as the start-ing materials. Their chemical structures were con?rmed by ¹H NMR, IR and HRMS tech-niques. The bioassay test results showed that 5b and 9b had good calm activity.

Key words: helicid, quinoline, flavone, hypnotic-sedative