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. (Graph Presented).
| Original language | English |
|---|---|
| Pages (from-to) | 459-469 |
| Number of pages | 11 |
| Journal | ACS Combinatorial Science |
| Volume | 17 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2015 Aug 10 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
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When Indolizine Meets Quinoline : Diversity-Oriented Synthesis of New Polyheterocycles and Their Optical Properties. / Park, Sujin; Kwon, Dah In; Lee, Jeeyeon; Kim, Ikyon.
In: ACS Combinatorial Science, Vol. 17, No. 8, 10.08.2015, p. 459-469.Research output: Contribution to journal › Article
TY - JOUR
T1 - When Indolizine Meets Quinoline
T2 - Diversity-Oriented Synthesis of New Polyheterocycles and Their Optical Properties
AU - Park, Sujin
AU - Kwon, Dah In
AU - Lee, Jeeyeon
AU - Kim, Ikyon
PY - 2015/8/10
Y1 - 2015/8/10
N2 - 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. (Graph Presented).
AB - 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. (Graph Presented).
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UR - http://www.scopus.com/inward/citedby.url?scp=84938829236&partnerID=8YFLogxK
U2 - 10.1021/acscombsci.5b00031
DO - 10.1021/acscombsci.5b00031
M3 - Article
VL - 17
SP - 459
EP - 469
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 8
ER -