The first example of a tandem thionation/S-cyclization process leading to benzo[c] thiophene-1(3H)-thione and 1H-isothiochromene-1-thione derivatives, starting from 2-alkynylbenzoic acids, is reported. The reaction is carried out in CH2Cl2 using 1 equiv of Lawesson's reagent under MW irradiation at 100 degrees C and 300W for 1h. Depending on the nature of the substituent at the distal beta 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.
A new microwave-assisted thionation-heterocyclization process leading to benzo[c] thiophene-1(3H)-thione and 10H-isothiochromene-1-thione derivatives
CHIACCHIO, Ugo;
2016-01-01
Abstract
The first example of a tandem thionation/S-cyclization process leading to benzo[c] thiophene-1(3H)-thione and 1H-isothiochromene-1-thione derivatives, starting from 2-alkynylbenzoic acids, is reported. The reaction is carried out in CH2Cl2 using 1 equiv of Lawesson's reagent under MW irradiation at 100 degrees C and 300W for 1h. Depending on the nature of the substituent at the distal beta 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.File in questo prodotto:
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