Document Type: Original Research Article

Authors

1 Department of Chemistry, Islamic Azad University, Qaemshahr Branch, P.O. Box 163, Qaemshahr, Iran

2 Department of Chemistry, Qaemshahr Branch, Islamic Azad University, P.O. Box 163, Qaemshahr, Iran

3 Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Tehran, Iran

Abstract

Derivatives of thiazolidinone ring systems are known to act as anti-HIV infections , analgesic, anti-bacterial, anti-convulsant, anti parasitic, potential anti-inflammatory and herbicidal agents. Due biological activities of thiazolidinones ring, several methods for their synthesis have been illustrated in literature. Imidazolidine-2-thiones were synthesized by the oxidative cyclization of 1-benzoyl-3-aryl-thioureas with bromine and enolizable carbonyl compounds in the presence of excess triethylamine . A suitable method for the synthesis of fused thiazoles were described from the reaction of aroylphenyl thioureas with π-acceptor quinones. An efficient and one-pot method for the synthesis alkyl 2-(1-alkyl-5-oxo-3-phenyl-2-thioxotetrahydro-4H-imidazol-4-yliden) acetate derivatives via simple reaction between isoquinoline, dialkyl acetylenedicarboxylate and benzyl phenylthiourea under solvent-free conditions without using any additional catalyst, is described. The mild reaction conditions and good yields and exhibit the synthetic advantage of this method. Also this method is environmentally friendly.

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[1] M.L. Barreca, J. Balzarini, A. Chimirri, E. De Clercq, L. De Luca, H.D. Holtje, M. Holtje, A.M. Monforte, P. Monforte, C. Pannecouque, A. Rao, M. Zappala, J. Med. Chem., 2002, 45, 5410.

[2] Y.X. Li, S.H. Wang, Z.M. Li, N. Su, W.G. Zhao, Carbohydrate Res. 2006, 341, 2867.

[3] G. Kucukguzel, A. Kocatepe, E. De Clercq,  F. Sahin, M. Gulluce, Eur. J. Med. Chem., 2006, 41, 353.

[4] T. Kato, T. Ozaki, K. Tamura, Y. Suzuki, M. Akima, N. Ohi, J. Med. Chem., 1998, 41, 4309.

[5] R.P. Tenorio, C.S. Carvalho,  C.S. Pessanha, J.G. de Lima, A.R. de Faria, A.J. Alves,  E.J.T. de Melo, A.J.S. Goes, Bioorg. Med. Chem. Lett., 2005, 15, 2575.

[6] S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin, A. Ozbek, Eur. J. Med. Chem., 2002, 37, 197.

[7] M.H. Shih, F.Y. Ke, Bioorg. Med. Chem., 2004, 12, 4633.

[8] F.W. Short, B.C. Littleton, J.L. Johnson, Chem. Ind. (London), 1971, 705.

[9] J. Hartung, K. Rosenbaum, L. Beyer, J. Losada, V. Fernandez, J. Prakt. Chem., 1991, 333, 537.

[10] R.-S. Zeng, J.-P. Zou, S.-J. Zhi, J. Chen, Q. Shen, Org. Lett., 2003, 5, 1657.

[11] A.A. Aly, E.K. Ahmed, K.M. El-Mokadem, J. Sulf. Chem., 2006, 27, 419.

[12] A. Manaka, T. Ishii, K. Takahashi, M. Sato, Tetrahedron Lett., 2005, 46, 419.

[13] A.A. Aly, E.K. Ahmed, K.M. El-Mokadem, J. Sulf. Chem., 2007, 28, 285.

[14] Y. Kihara, S. Kabashima, K. Uno, T. Okawara, T. Yamasaki, M. Furukawa, Synthesis, 1990, 1020.

[15] A.A. Aly, E.K. Ahmed, K.M. El-Mokadem, J. Heterocycl. Chem., 2007, 44, 1431.

[16] N.A. Danilkina, L.E. Mikhailov, B.A. Ivin, In the 3rd Euro-Asian Heterocyclic Meeting “Heterocycles in organic and combinatorial chemistry ” (EAHM-2004) September 12 – 17, 2004 Novosibirsk, Russia.

[17] A.B. Brown, M. Abdel-Aziz, G.E.-D.A.A. Abuo-Rahma, M.F. Radwan, M. Ramadan, A.M. Gamal-Eldeen, J. Heterocyclic Chem., 2012, 49, 726.