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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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Publication details

The article was received on 01 Nov 2018, accepted on 09 Dec 2018 and first published on 10 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01182F
Citation: Org. Chem. Front., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C8QO01182F

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