A regioselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-chromene thiadiazole derivatives |
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Affiliation: | 1. Laboratoire de chimie hétérocyclique, produits naturels et réactivité (LR11ES39), Équipe Chimie bioorganique et produits naturels, faculté des sciences de Monastir, université de Monastir, 5000 Monastir, Tunisia;2. Centre de recherche de Gif, Institut de chimie des substances naturelles, CNRS, avenue de la Terrasse, 91198 Gif-sur-Yvette cedex, France |
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Abstract: | A variety of 4′-(4-R-phenyl)-4-(methylthio)-2′-phenyl-2′H-spiro[chromene-2,5′-[1,2,3]thiadiazole] 5a–d and 5′-(4-R-phenyl)-4-(methylthio)-3′-phenyl-3′H-spiro[chromene-2,2′-[1,3,4]thiadiazole] 6a–d were synthesized regioselectively through the reaction of 4-(methylthio)-2H-chromene-2-thione 2 with diarylnitrilimines under refluxing dry chloroform. Whilst the reaction of 4-(allylthio)-2H-chromene-2-thione 3 with diarylnitrilimines under similar reaction conditions afforded the corresponding 4-(allylthio)-5′-(4-R-phenyl)-3′-phenyl-3′H-spiro[chromene-2,2′-[1,3,4]thiadiazole] 7a–d and 5-(4-R-phenyl)-2′-methyl-3-phenyl-2′,3′-dihydro-3H-spiro[[1,3,4]thiadiazole-2,4′-thieno[3,2-c]chromene] 9a–d as two unisolable diastereoisomeric forms. The structures of the obtained spiro cycloadduct thiadiazoles have been assigned by means of spectroscopic measurements. |
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Keywords: | 1,3-Dipolar cycloaddition Diarylnitrilimines Regioselective Spiro cycloadduct thiadiazoles |
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