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Iron-Catalyzed Transfer Hydrogenation: Divergent Synthesis of Quinolines and Quinolones from ortho-Nitrobenzyl Alcohols

Cited 1 time in Web of Science Cited 1 time in Scopus
Authors

Chun, Simin; Putta, Ramachandra Reddy; Hong, Junhwa; Choi, Seung Hyun; Oh, Dong-Chan; Hong, Suckchang

Issue Date
2023-10
Publisher
John Wiley & Sons Ltd.
Citation
Advanced Synthesis & Catalysis, Vol.365 No.19, pp.3367-3374
Abstract
Herein, we report the divergent synthesis of quinolines and quinolones via a transfer hydrogenative condensation of ortho-nitrobenzyl alcohols in one step. The reaction proceeded using the cyclopentadienone iron complex without any additional redox reagents. After transfer hydrogenation between ortho-nitrobenzyl alcohols and secondary alcohols, the subsequent Friedlander annulation affords polysubstituted quinoline products in 22-90% (39 examples). The developed method was also applied to synthesize quinolones by using primary alcohols instead of secondary alcohols (12 examples). The obtained quinoline products were converted into several drug candidates to demonstrate its synthetic potential.
ISSN
1615-4150
URI
https://hdl.handle.net/10371/201982
DOI
https://doi.org/10.1002/adsc.202300661
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  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Development of methodologies using metal catalyst, Total synthesis of natural products

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