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When Indolizine Meets Quinoline: Diversity-Oriented Synthesis of New Polyheterocycles and Their Optical Properties.

Authors :
Sujin Park
Dah In Kwon
Jeeyeon Lee
Ikyon Kim
Source :
ACS Combinatorial Science. Aug2015, Vol. 17 Issue 8, p459-469. 11p.
Publication Year :
2015

Abstract

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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
21568952
Volume :
17
Issue :
8
Database :
Academic Search Index
Journal :
ACS Combinatorial Science
Publication Type :
Academic Journal
Accession number :
108955567
Full Text :
https://doi.org/10.1021/acscombsci.5b00031