Solvent-Free Condensation Reactions To Synthesize Five-Membered Heterocycles Containing the Sulfamide Fragment

Abstract

We report a study of the solvent-free condensation reaction of 1,2-dicarbonyl compounds with sulfamide catalyzed by a Keggin-type acid (H₃PMo₁₂O₄₀·nH₂O, MPA) to obtain 3,4-disubstituted 1,2,5-thiadiazole 1,1-dioxide derivatives. Some reactions were also performed in solution or using nano-sized silica-supported MPA catalyst in order to compare the results under different experimental conditions. Effects of the temperature used for the thermal pretreatment of the catalyst, the reaction temperature, the molar ratios sulfamide/1,2-dicarbonyl compound and MPA/1,2-dicarbonyl compound, and alternative experimental procedures on the yield of the reaction product were investigated. Under suitable experimental conditions eight compounds were obtained in good yields. The catalyst was recycled and reused, but with some loss of its catalytic activity. The presented synthetic method is a simple, clean, and environmentally friendly alternative for synthesizing different 1,2,5-thiadiazole 1,1-dioxide derivatives.

Key words

heterocycles - solvent-free reaction - condensation - acid catalysis - heteropolyacids - 1,2-dicarbonyl compounds - sulfamide

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