Synthesis 2019; 51(24): 4611-4618
DOI: 10.1055/s-0037-1610730
paper
© Georg Thieme Verlag Stuttgart · New York

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

Jeong A Yoon
,
Young Taek Han
College of Pharmacy, Dankook University, Chenan 31119, Korea   Email: hanyt@dankook.ac.kr
› Author Affiliations
This work was supported by the National Research Foundation of Korea with a grant funded by the Ministry of Science, ICT and Future Planning (NRF-2017R1C1B1001826).
Further Information

Publication History

Received: 29 July 2019

Accepted after revision: 04 September 2019

Publication Date:
30 September 2019 (online)

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.

Supporting Information

 
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