When Indolizine Meets Quinoline

Diversity-Oriented Synthesis of New Polyheterocycles and Their Optical Properties

Sujin Park, Dah In Kwon, Jeeyeon Lee, Ikyon Kim

Research output: Contribution to journalArticle

21 Citations (Scopus)

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 languageEnglish
Pages (from-to)459-469
Number of pages11
JournalACS Combinatorial Science
Volume17
Issue number8
DOIs
Publication statusPublished - 2015 Aug 10

Fingerprint

Quinolines
Optical properties
Cyclization
Indolizines
Fluorophores
Fluorescent Dyes
Aldehydes
Condensation
Fluorescence
indolizine
quinoline

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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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).",
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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 journalArticle

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