A new microwave-assisted thionation-heterocyclization process leading to benzo[c]thiophene-1(3H)-thione and 1H-isothiochromene-1-thione derivatives. Issue 25 (19th February 2016)

• Record Type: Journal Article
• Authors: Giofrè, Salvatore V.; Romeo, Roberto; Mancuso, Raffaella; Cicero, Nicola; Corriero, Nicola; Chiacchio, Ugo; Romeo, Giovanni; Gabriele, Bartolo
• Is Part Of: RSC advances. Volume 6:Issue 25(2016)
• Page Start: 20777
• Page End: 20780
• Publication Date: 2016-02-19
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra01329e
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : The first example of a MW-assisted tandem thionation/ S -cyclization process, leading to benzothiophenethione and isothiochromenethione derivatives, is reported. Abstract : The first example of a tandem thionation/ S -cyclization process leading to benzo[ c ]thiophene-1(3 H )-thione and 1 H -isothiochromene-1-thione derivatives, starting from 2-alkynylbenzoic acids, is reported. The reaction is carried out in CH2 Cl2 using 1 equiv. of Lawesson's reagent under MW irradiation at 100 °C and 300 W for 1 h. Depending on the nature of the substituent at the distal β carbon of the triple bond, either benzothiophenethiones or isothiochromenethiones were obtained selectively, in high to excellent yields. The structure of the representative compounds has been confirmed by X-ray diffraction analysis.