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■ Reactions of Tetrasulfur Tetranitride Antimony Pentachloride Complex (S₄N₄·SbCl₅) with Primary β-Enaminones and β-Enamino Esters: Synthesis of 4-Substituted 3-Aroyl- and 3-Ethoxycarbonyl-1,2,5-thiadiazoles

Su-Hak Bae, Kyongtae Kim,* and Young Ja Park

*Department of Chemistry, Seoul National University, Seoul 151-742, Korea

Abstract

The reaction of tetrasulfur tetranitride antimony pentachloride complex (S₄N₄·SbCl₅) with 3-amino-3-alkyl-1-aryl-2-propenones and 3-amino-1,3-diaryl-2-propenones in toluene at 100°C produced 4-substitued 3-aroyl-1,2,5-thiadiazoles (3a-p) in 12 to 57% yields. Similarly treatment of β-enamino esters with S₄N₄.SbCl₅ complex under the same conditions as for the reaction with β-enaminones gave ethyl 3-aryl-1,2,5-thiadizole-4-carboxylates (3q-x) in 41 to 54% yields. The formation of the products may be explained by the same mechanism as that proposed for the formation of 1,2,5-thiadizoles from 5-substitued 3-alkyl- and 3-aryl-isoxazoles and S₄N₄.SbCl₅ complex.