Nucleophilic intramolecular cyclization reactions of alkynechalcogenolates

…, B D'hooge, ML Petrov, S Smeets, S Toppet, M Voets

Index: Abramov; Dehaen; D'Hooge; Petrov; Smeets; Toppet; Voets Tetrahedron, 2000 , vol. 56, # 24 p. 3933 - 3940

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Citation Number: 56

Abstract

2-(ortho-Hydroxyphenyl)-alkynethiolates and-selenolates, obtained through base catalyzed ring cleavage of 4-(ortho-hydroxyphenyl)-1, 2, 3-thiadiazoles and-1, 2, 3-selenadiazoles, smoothly transform into 2-benzofuranthiolates and-selenolates. These reactive intermediates can be alkylated in high yield. This reaction sequence could be applied to the synthesis of electron rich thiacrown ethers. The 2-(ortho-aminophenyl)-alkynethiolate ...