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Studies on 4-Thiazolidinones: Scope of the Reactions of 3-Aryl-2-thioxo-1,3-thiazolidin-4-ones with Cyanide and Cyanate Ions

✍ Scribed by Mohamed T. Omar; Mohamed E. Shaban; Nadia K. El-Aasar; Khaled F. Saied

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
224 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Treatment of 3‐aryl‐2‐thioxo‐1,3‐thiazolidin‐4‐ones 1 with CN^−^ and NCO^−^ effected the ring cleavage providing [(cyanocarbonothioyl)amino]benzenes 4 and arylisothiocyanates 5, respectively. Similar treatment of 5‐(2‐aryl‐2‐oxoethyl) derivatives 2 afforded 2,4‐bis(2‐aryl‐2‐oxoethylidene)cyclobutane‐1,3‐diones 6 along with each of the preceding products. Treatment of the respective (E,Z)‐5‐(2‐aryl‐2‐oxoethylidene) analogues 3b and 3c with CN^−^ gave 4b and 4c and 2‐(arylcarbonyl)‐2‐methoxy‐4‐oxopentanedinitriles 7b and 7c, in addition to 3,6‐bis[2‐(4‐chlorophenyl)‐1‐methoxy‐2‐oxoethylidene]‐1,4‐dithiane‐2,5‐dione 8c, which has been generated from 3c. Reactions of 3c or 3d with NCO^−^ provided 5c or 5d, together with 8c or 8d as pure isomers. In the formation of the MeO products 7 and 8, the solvent (MeOH) has participated. Structures of these products are based on microanalytical and spectroscopic data. Rationalizations for the above transformations are given.

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