Efficient Synthesis of Pyrido[3,2-c]coumarins via Silver Nitrate Catalyzed Cycloisomerization and Application to the First Synthesis of Polyneomarline C

Abstract

Herein, we report an efficient method for the synthesis of the pyrido[3,2-c]coumarin scaffold, one of the privileged heterocycle-fused coumarin scaffolds, via a AgNO₃-catalyzed cycloisomerization of 4-(propynylamino)coumarins obtained from diverse 4-hydroxycoumarins. This concise method affords pyrido[3,2-c]coumarin analogues bearing diverse substituents on the benzene or pyridine ring in moderate to good yields. Moreover, this methodology was extended to the facile synthesis of polyneomarline C, a natural pyrido[3,2-c]coumarin derivative isolated from the Chinese herbal medicine Polyalthia nemoralis A. DC., in three steps and in 26% overall yield from the known 4-hydroxycoumarin.

Key words

cycloisomerization - pyrido[3,2-c]coumarin - polyneomarline C - heterocycle-fused coumarin - propargylamine

• References

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