Jump to main content
Jump to site search


NaHSO4/SiO2 catalyzed generation of o-quinone/ o-thioquinone methides: synthesis of arylxanthenes/ arylthioxanthenes via oxa-6π-electrocyclization

Author affiliations

Abstract

ortho-Quinone methides, very reactive transient intermediates, are utilized successfully in synthesizing complex organic molecules of natural and biological significance. Among several synthetic protocols, the acid catalyzed generation of ortho-quinone methides from suitably substituted phenols is a promising method for further exploitation in organic synthesis. Such an interesting reactive species is conveniently employed in the synthesis of conformationally restricted triarylmethane derivatives such as 12/9-arylxanthenes/arylthioxanthenes starting from symmetrical/unsymmetrical 2-(hydroxydiarylmethyl)phenol/thiophenol, respectively, using SiO2–NaHSO4. Conformationally restricted 12/9-arylxanthenes/arylthioxanthenes were obtained in 52 to 96% yields using this protocol, which is believed to involve the formation of o-quinone methides followed by electrocyclic ring closure and isomerization at elevated temperature. Photophysical studies of selected examples in acidic media showed turn-on fluorescence by hydride ion transfer mediated π-conjugated xanthylium salt formation and suggested the application potential in bio-imaging and fluorescent sensors.

Graphical abstract: NaHSO4/SiO2 catalyzed generation of o-quinone/ o-thioquinone methides: synthesis of arylxanthenes/ arylthioxanthenes via oxa-6π-electrocyclization

Back to tab navigation

Supplementary files

Article information


Submitted
09 Sep 2020
Accepted
05 Oct 2020
First published
09 Oct 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

NaHSO4/SiO2 catalyzed generation of o-quinone/ o-thioquinone methides: synthesis of arylxanthenes/ arylthioxanthenes via oxa-6π-electrocyclization

M. Karthick, E. Konikkara Abi, N. Someshwar, S. P. Anthony and C. R. Ramanathan, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB01868F

Social activity

Search articles by author

Spotlight

Advertisements