European Journal of Chemistry

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



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

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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Mahmoud, M. R.; Madkour, H. M. F.; El-Bordany, E. A. E.-F.; Soliman, E.-S. A. Synthesis and Reactions of (Z)-2-Imino-5-(3,4,5-Trimethoxy benzylidene)thiazolidin-4(H)one. Eur. J. Chem. 2011, 2, 475-479.

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References

[1]. Salem, M. A. I.; Soliman, E. A.; Smith, M. B.; Mahmoud, M. R.; Azab, M. E. Phosphorus Sulfur 2004, 179, 61-67.
http://dx.doi.org/10.1080/10426500490257041

[2]. Pellicciari, R. P.; Natalini, B.; Costantino, G.; Mahmoud, M. R.; Mattoli, I.; Sadeghpour, B. M. J. Med. Chem. 1994, 37(5), 647-655.
http://dx.doi.org/10.1021/jm00031a015
PMid:8126705

[3]. Mahmoud, M. R.; El-Bordany E. A. A.; Azab M. E.; Soliman E. A. Phosphorus Sulfur 2007, 181, 1275-1289.
http://dx.doi.org/10.1080/10426500601160785

[4]. Mahmoud, M. R.; El-Bordany, E. A. A.; Hassan, N. F.; Abu El-Azm, F. S. M. Phosphorus Sulfur 2007, 182, 2507-2521.

[5]. Mahmoud, M. R.; Madkour, H. M. F.; El-Bordany E. A. A.; Soliman E. A. J. Chem. Res. 2007, 11, 673-676.

[6]. Mahmoud, M. R.; El-Shahawi, M. M.; Farahat, S. E. J. Chem. Res. 2008, 1, 59-60.

[7]. Mahmoud, M. R.; El-Shahawi, M. M.; Farahat, S. E. J. Chem. Res. 2008, 2, 86-88.

[8]. Kambe, S.; Satio, K.; Sakurai, A.; Midorikawa, H. Synthesis 1981, 7, 531-532.
http://dx.doi.org/10.1055/s-1981-29513

[9]. Madkour, H. M. F.; Mahmoud, M. R.; Nassar, M. H.; Habashy, M. M. Sulphur letters 1998, 21(6), 253-261.

[10]. Pretsh, E.; Clerc, T.; Seibl, J.; Simon, W. Tables of spectral data for structure determination of organic compounds, Springer-Verlag, 1989, 2nd ed. pp. 215 and H 220.

[11]. Omar, M. T.; Fouli, F. A.; Elgarhi, M. Z. Bull. Chem. Soc. Jpn. 1991, 64, 750-752.
http://dx.doi.org/10.1246/bcsj.64.750

[12]. Raouf, A. R. A.; Omar, M. T.; Elattal, M. M. Acta. Chim. Acad. Sci. 1975, 87, 187-192.

[13]. Yiang, Y.; Chem, J.; Schinazi, R.; Zhao, K. Tetrahedron Lett. 1995, 36(40), 7193-7196.
http://dx.doi.org/10.1016/0040-4039(95)01499-8

[14]. Omar, M. T.; Habashy, M. M.; Shaban, M. E.; Kasem, M. A. Synthesis 1981, 4, 318-318.
http://dx.doi.org/10.1055/s-1981-29436

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