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Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one
Mahmoud Refaee Mahmoud (1,*) , Hassan Mohamed Fawzy Madkour (2) , Eman Abd El-Fattah El-Bordany (3) , El-Sayed Ahmed Soliman (4)
(1) Chemistry Department, Faculty of Science, Ain Shams University, Cairo, 11566, Egypt
(2) Chemistry Department, Faculty of Science, Ain Shams University, Cairo, 11566, Egypt
(3) Chemistry Department, Faculty of Science, Ain Shams University, Cairo, 11566, Egypt
(4) Chemistry Department, Faculty of Science, Ain Shams University, Cairo, 11566, Egypt
(*) Corresponding Author
Received: 02 Jul 2010 | Accepted: 08 Dec 2010 | Published: 31 Dec 2011 | Issue Date: December 2011
5-Arylmethylene-2-imino-4-oxo-2-thiazolidine 3 was obtained as the sole product from the reaction of α-cyano-3,4,5-trimethoxy cinnamonitrile and/or ethyl-α-cyano-3,4,5-trimethoxy cinnamate (1a,b) with 2-imino-4-oxo-2-thiazolidine 2. The reaction of 3 with benzyl amine gave the imidazolidin-4(H)one derivative 4 while with hydrazine hydrate afforded the dimeric product 5. Also, reaction of thiazolidinone derivative 3 with piperidine gave thiazol-4(5H)one derivative 6 which on treatment with Grignard reagent and active methylene compounds afforded thiazolidin-4-one derivatives 7-9, respectively. Compound 6 was converted to the potassium salt 10 which treated with acetic acid, ethyl chloroacetate and furoyl chloride to give the compounds 11-13, respectively. The structures of all new compounds were evidenced by microanalytical data and spectral data.
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DOI Link: https://doi.org/10.5155/eurjchem.2.4.475-479.193
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European Journal of Chemistry 2011, 2(4), 475-479 | doi: https://doi.org/10.5155/eurjchem.2.4.475-479.193 | Get rights and content
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