Synthesis of indolo- and benzothieno[3,2-c]quinolines via POCl<inf>3</inf> mediated tandem cyclization of o-alkynylisocyanobenzenes derived from o-alkynyl-N-phenylformamides
Issued Date
2022-08-01
Resource Type
ISSN
11440546
eISSN
13699261
Scopus ID
2-s2.0-85136172745
Journal Title
New Journal of Chemistry
Volume
46
Issue
34
Start Page
16333
End Page
16340
Rights Holder(s)
SCOPUS
Bibliographic Citation
New Journal of Chemistry Vol.46 No.34 (2022) , 16333-16340
Suggested Citation
Uppalabat T., Tapdara A., Khaikate O., Worakul T., Surawatanawong P., Leowanawat P., Soorukram D., Reutrakul V., Meesin J., Kuhakarn C. Synthesis of indolo- and benzothieno[3,2-c]quinolines via POCl<inf>3</inf> mediated tandem cyclization of o-alkynylisocyanobenzenes derived from o-alkynyl-N-phenylformamides. New Journal of Chemistry Vol.46 No.34 (2022) , 16333-16340. 16340. doi:10.1039/d2nj02791g Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/84067
Title
Synthesis of indolo- and benzothieno[3,2-c]quinolines via POCl<inf>3</inf> mediated tandem cyclization of o-alkynylisocyanobenzenes derived from o-alkynyl-N-phenylformamides
Author's Affiliation
Other Contributor(s)
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.