170645-27-9Relevant academic research and scientific papers
Studies on 4-thiazolidinones: Scope of the reactions of 3-aryl-2-thioxo-1,3-thiazolidin-4-ones with cyanide and cyanate ions
Omar, Mohamed T.,Shaban, Mohamed E.,El-Aasar, Nadia K.,Saied, Khaled F.
experimental part, p. 1461 - 1470 (2009/02/07)
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.
Nucleophilic addition to the exocylic double bond of 5-substituted 2-thioxo-4-oxothiazolidines
Omar,Youssef,Nessim
, p. 75 - 92 (2007/10/03)
THE REACTIVITY of the exocyclic double bond at position-5 of the 2-thioxo-4-oxothiazolidine ring system towards the addition of nucleophiles has been studied, aiming to synthesize spiro benzothiazolothiazoles 5, benzothiazines 8 and benzopyrazines 13 deri
The (E)/(Z)-Ratio in the Reaction of 5-(2-Aryl-2-oxoethyl)-2-thioxo-4-oxo-1,3-thiazolidines with Bromine
Omar, M. T.,Kandeel, K. A.,Youssef, A. S. A.
, p. 439 - 446 (2007/10/02)
3-Aryl, 3-benzyl-, and 3H-5-(2-aryl-2-oxoethyl)-2-thioxo-4-oxo-1,3-thiazolidines 3a-h react with bromine in acetic acid solution to give mixtures of the respective 5-aroylmethylene (E) and (Z) diastereomeric derivatives 5 and 6.They contain more than 85percent of the (E)-diastereomers along with some pure isomers.The intermediacy of the 5-bromo derivatives 4 is proven and a plausible route of the reaction is presented.Structures of compounds 3-6 are evidenced by analytical and spectral data. - Keywords: (E)- and (Z)-3-Aryl-, 3-Benzyl-, and 3H-5-Aroylmethylene-2-thioxo-4-oxo-1,3-thiazolidines; (E)- and (Z)-5-Aroylmethylene-2,4-dioxo-1,3-thiazolidines; Bromine; Configurational assignment
