期刊
ACS COMBINATORIAL SCIENCE
卷 17, 期 8, 页码 459-469出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.5b00031
关键词
Pictet-Spengler cyclization; fluorescence-based technologies; indolizine; quinoline; polyheterocycles
资金
- Nano-Material Technology Development Program through National Research Foundation of Korea (NRF) - Ministry of Education, Science and Technology
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [2014R1A2A1A11050491]
- Global Frontier Program for the Intelligent Synthetic Biology [NRF-2011-0032201]
- National Research Foundation of Korea (NRF) - Korean government (MSIP) [2009-0083533]
- Seoul National University
Fluorescence-based technologies play a pivotal role in various biomedical applications. Here we report an efficient route to a new class of fluorophores, indolizino [3,2-c]quinolines, via the oxidative Pictet-Spengler cyclization strategy. The condensation of several 2-methylpyridines with 2-bromo-2'-nitroacetophenone allowed for the rapid assembly of indolizines with a 2-nitrophenyl group at the C2 position. The subsequent reduction of the nitro group under mild conditions followed by oxidative Pictet-Spengler cyclization with various aryl aldehydes in the presence of a catalytic amount of FeCl3 furnished the indolizino[3,2-c] quinolines in good overall yields. We also examined the photophysical properties of this new series of polyheterocyclic compounds. Several indolizino[3,2-c]quinolines were found to have unique and desirable optical properties, suggesting that these compounds may be suitable for use as prospective fluorescent probes in aqueous systems.
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