Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 17
511
Views
11
CrossRef citations to date
0
Altmetric
Articles

Synthesis of new thioxanthenes by organocatalytic intramolecular Friedel–Crafts reaction

Pages 2177-2188 | Received 05 Apr 2018, Published online: 16 Jul 2018
 

Abstract

An efficient organocatalytic route has been developed to synthesize novel substituted thioxanthenes (2a2v) starting from diaryl thioether alcohols (1a1v) using the intramolecular Friedel–Crafts reaction. The starting materials were obtained in two stages via a coupling reaction followed by the Grignard reaction. In this study, we tried for the first time to use some organic Brønsted acids as organocatalysts (3a3h) in the intramolecular Friedel–Crafts cyclization reaction of thioether alcohols. The synthesis of original substituted thioxanthenes was achieved within 15 minutes by using N-triflylphosphoramide (3h) with quantitative yields in THF at room temperature.

Graphical Abstract

Supplementary information

Experimental details, analytical data for all compounds and copies of 1H NMR, 13C NMR spectra, GC-MS and elemental analysis are provided.

Acknowledgments

This work was supported by Istanbul University, Scientific Research Projects, project number BYP-2017-24039.

Disclosure statement

No potential conflict of interest was reported by the author.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.