Synthesis of indolo- and benzothieno[3,2-c]quinolines via POCl3 mediated tandem cyclization of o-alkynylisocyanobenzenes derived from o-alkynyl-N-phenylformamides?
New Journal of Chemistry Pub Date: 2022-08-01 DOI: 10.1039/D2NJ02791G
Abstract
A synthesis of indolo[3,2-c]quinolines and benzothieno[3,2-c]quinolines has been developed employing o-alkynyl-N-phenylformamide derivatives as the substrates. The reaction proceeded via a tandem process involving POCl3-assisted intramolecular cyclization of the firstly formed o-alkynylisocyanobenzenes, leading to the desired products in moderate to high yields. Furthermore, the reaction is efficient on a gram-scale and the products were structurally modified by amination, Suzuzki-Miyaura reaction and Heck cross-coupling. Photophysical properties of several selected indolo[3,2-c]quinolines were studied by UV-Visible and fluorescence spectroscopy and rationalized using time-dependent DFT calculations.
![Graphical abstract: Synthesis of indolo- and benzothieno[3,2-c]quinolines via POCl3 mediated tandem cyclization of o-alkynylisocyanobenzenes derived from o-alkynyl-N-phenylformamides](http://scimg.chem960.com/usr/1/D2NJ02791G.jpg)
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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