Synthesis and reactions of  (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one

Mahmoud Refaee Mahmoud; Hassan Mohamed Fawzy Madkour; Eman Abd El-Fattah El-Bordany; El-Sayed Ahmed Soliman

doi:10.5155/eurjchem.2.4.475-479.193

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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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

Abstract

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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Keywords

Iminothiazolidinone derivatives; Grignard reagents; Imidazolidinone derivative; 2-Thiazolidin-4-one; Nitrogen nucleophiles; Activated nitriles

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DOI: 10.5155/eurjchem.2.4.475-479.193

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Citations

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An Efficient and Convenient Synthesis of Certain 2-Thioxothiazole,2-oxo-1,2-dihydropridine, 2-Oxo-2<i>H</i>-pyran,2,4-diaminothiophene and Pyrazolo[5,1-c][1,2,4]triazine Derivatives Containing Antipyrine Moiety
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5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry
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Utility of Cyano-N-(2-oxo-1,2-dihydroindol-3-ylidene)acetohydrazide in the Synthesis of Novel Heterocycles
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Organic Chemistry Frontiers 7(20), 3284, 2020
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How to cite

Mahmoud, M.; Madkour, H.; El-Bordany, E.; Soliman, E. Eur. J. Chem. 2011, 2(4), 475-479. doi:10.5155/eurjchem.2.4.475-479.193

Mahmoud, M.; Madkour, H.; El-Bordany, E.; Soliman, E. Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one. Eur. J. Chem. 2011, 2(4), 475-479. doi:10.5155/eurjchem.2.4.475-479.193

Mahmoud, M., Madkour, H., El-Bordany, E., & Soliman, E. (2011). Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one. European Journal of Chemistry, 2(4), 475-479. doi:10.5155/eurjchem.2.4.475-479.193

Mahmoud, Mahmoud, Hassan Mohamed Fawzy Madkour, Eman Abd El-Fattah El-Bordany, & El-Sayed Ahmed Soliman. "Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one." European Journal of Chemistry [Online], 2.4 (2011): 475-479. Web. 4 Jun. 2023

Mahmoud, Mahmoud, Madkour, Hassan, El-Bordany, Eman, AND Soliman, El-Sayed. "Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one" European Journal of Chemistry [Online], Volume 2 Number 4 (31 December 2011)

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DOI Link: https://doi.org/10.5155/eurjchem.2.4.475-479.193

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