

Synthesis and reactions of (Z)-2-imino-5-(3,4,5-trimethoxy benzylidene)thiazolidin-4(H)one
Mahmoud Refaee Mahmoud (1,*)




(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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DOI: 10.5155/eurjchem.2.4.475-479.193
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[1]. Seif-Eldin Nasr Ayyad, Fathy Muhammad Abdelaziz El-Taweel, Abdel-Ghani Ali Elagamey, Tahani Mahmoud El-Mashad
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
International Journal of Organic Chemistry 02(02), 135, 2012
DOI: 10.4236/ijoc.2012.22021

[2]. Sreenu Pavurala, Krishnaiah Vaarla, Rajeswar Rao Vedula
One-pot synthesis of bis (phenylimino dihydro thiazolyl-2H-chromene) derivatives
Synthetic Communications 47(4), 330, 2017
DOI: 10.1080/00397911.2016.1263891

[3]. Danylo Kaminskyy, Anna Kryshchyshyn, Roman Lesyk
5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry
European Journal of Medicinal Chemistry 140, 542, 2017
DOI: 10.1016/j.ejmech.2017.09.031

[4]. Mahmoud R. Mahmoud, Ahmed K. El-Ziaty, Fatma S. M. Abu El-Azm, Mahmoud F. Ismail, Sayed A. Shiba
Utility of Cyano-N-(2-oxo-1,2-dihydroindol-3-ylidene)acetohydrazide in the Synthesis of Novel Heterocycles
Journal of Chemical Research 37(2), 80, 2013
DOI: 10.3184/174751912X13567100793191

[5]. Katarina L. Keel, Jetze J. Tepe
The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products
Organic Chemistry Frontiers 7(20), 3284, 2020
DOI: 10.1039/D0QO00764A

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

















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