Issue 10, 2011

Photochemical intramolecular cyclization of o-alkynylaryl isocyanides with organic dichalcogenides leading to 2,4-bischalcogenated quinolines

Abstract

When a mixture of o-alkynylaryl isocyanides and organic dichalcogenides such as diselenides or ditellurides was irradiated with light of wavelength over 300 or 400 nm, the intramolecular cyclization of the isocyanides took place to afford the corresponding 2,4-bischalcogenated quinolines selectively. The photochemical cyclization of 2-(phenylethynyl)phenyl isocyanide could also proceed in the presence of hydrogen transfer reagents such as tris(trimethylsilyl)silane, tributylgermyl hydride, alkanethiols, and benzeneselenol, providing the corresponding 3-phenylquinoline as the result of 2,4-dihydrogenation.

Graphical abstract: Photochemical intramolecular cyclization of o-alkynylaryl isocyanides with organic dichalcogenides leading to 2,4-bischalcogenated quinolines

Supplementary files

Article information

Article type
Paper
Submitted
13 Dec 2010
Accepted
22 Mar 2011
First published
22 Mar 2011

Org. Biomol. Chem., 2011,9, 3768-3775

Photochemical intramolecular cyclization of o-alkynylaryl isocyanides with organic dichalcogenides leading to 2,4-bischalcogenated quinolines

T. Mitamura, K. Iwata, A. Nomoto and A. Ogawa, Org. Biomol. Chem., 2011, 9, 3768 DOI: 10.1039/C0OB01168A

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