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DOI: 10.1055/s-0037-1610730
Efficient Synthesis of Pyrido[3,2-c]coumarins via Silver Nitrate Catalyzed Cycloisomerization and Application to the First Synthesis of Polyneomarline C
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).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.
Key words
cycloisomerization - pyrido[3,2-c]coumarin - polyneomarline C - heterocycle-fused coumarin - propargylamineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610730.
- Supporting Information
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