- Studies on 4-thiazolidinones: Scope of the reactions of 3-aryl-2-thioxo-1,3-thiazolidin-4-ones with cyanide and cyanate ions
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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.
- Omar, Mohamed T.,Shaban, Mohamed E.,El-Aasar, Nadia K.,Saied, Khaled F.
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experimental part
p. 1461 - 1470
(2009/02/07)
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