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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[1]. Seif-Eldin Nasr Ayyad, Fathy Muhammad Abdelaziz El-Taweel, Abdel-Ghani Ali Elagamey, Tahani Mahmoud El-Mashad
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[2]. Sreenu Pavurala, Krishnaiah Vaarla, Rajeswar Rao Vedula
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DOI: 10.1080/00397911.2016.1263891
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[3]. Danylo Kaminskyy, Anna Kryshchyshyn, Roman Lesyk
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DOI: 10.1016/j.ejmech.2017.09.031
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[4]. Mahmoud R. Mahmoud, Ahmed K. El-Ziaty, Fatma S. M. Abu El-Azm, Mahmoud F. Ismail, Sayed A. Shiba
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Journal of Chemical Research  37(2), 80, 2013
DOI: 10.3184/174751912X13567100793191
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[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
/


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

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. 28 Nov. 2020
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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