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Issue 9, 2019
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One-pot sequential synthesis of 3-carbonyl-4-arylbenzo[f]indole and 3-carbonyl-4-arylnaphthofuran fluorophores

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Abstract

The development of novel methods for the construction of valuable fluorophores, 3-carbonyl-4-arylbenzo[f]indoles and 3-carbonyl-4-arylnaphthofurans, is described. In this protocol, the important polycarbonyl key intermediate was generated via the ketonization of ortho-alkynylarylketone tethered with a 1,3-dicarbonyl moiety. This intermediate reacted with an amine to selectively form a pyrrole intermediate, followed by cyclization in acetic acid to provide 3-carbonyl-4-arylbenzo[f]indole. Importantly, these conditions did not cause any epimerization of the stereogenic center in chiral amine substrates. Moreover, the polycarbonyl intermediate could also be utilized to prepare 3-carbonyl-4-arylnaphthofuran using In(OTf)3 as a catalyst for double cyclization under thermal conditions. In addition, the fluorescence properties of both fluorophores were also studied.

Graphical abstract: One-pot sequential synthesis of 3-carbonyl-4-arylbenzo[f]indole and 3-carbonyl-4-arylnaphthofuran fluorophores

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Supplementary files

Article information


Submitted
01 Nov 2018
Accepted
09 Dec 2018
First published
10 Dec 2018

Org. Chem. Front., 2019,6, 1340-1355
Article type
Research Article

One-pot sequential synthesis of 3-carbonyl-4-arylbenzo[f]indole and 3-carbonyl-4-arylnaphthofuran fluorophores

N. Supantanapong, P. Chuangsoongnern, J. Tummatorn, C. Thongsornkleeb and S. Ruchirawat, Org. Chem. Front., 2019, 6, 1340
DOI: 10.1039/C8QO01182F

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