期刊
NEW JOURNAL OF CHEMISTRY
卷 46, 期 34, 页码 16333-16340出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2nj02791g
关键词
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资金
- National Research Council of Thailand (NRCT)
- Mahidol University [N42A650344]
- Institute for the Promotion of Teaching Science and Technology through Science Achievement Scholarship of Thailand (SAST)
A highly efficient synthesis of indolo[3,2-c]quinolines and benzothieno[3,2-c]quinolines has been developed using o-alkynyl-N-phenylformamide derivatives as substrates. The reaction proceeds through a tandem process involving POCl3-assisted intramolecular cyclization of o-alkynylisocyanobenzenes, leading to the desired products in moderate to high yields. The synthesized products can be further modified, and the photophysical properties of selected indolo[3,2-c]quinolines were characterized and explained using time-dependent DFT calculations.
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.
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