When Indolizine Meets Quinoline: Diversity-Oriented Synthesis of New Polyheterocycles and Their Optical Properties
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- 作者：Sujin Park ; Dah In Kwon ; Jeeyeon Lee ; Ikyon Kim
- 刊名：ACS Combinatorial Science
- 出版年：2015
- 出版时间：August 10, 2015
- 年：2015
- 卷：17
- 期：8
- 页码：459-469
- 全文大小：660K
- ISSN：2156-8944
文摘
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鈥揝pengler cyclization strategy. The condensation of several 2-methylpyridines with 2-bromo-2鈥?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鈥揝pengler 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.