A Novel One-Pot Green Synthesis and Characterization of Substitue Bis-Iminothiazolidinones

Year 2018, Volume: 5 Issue: 3, 1061 - 1070, 01.09.2018

Fatma Tülay Tugcu

https://doi.org/10.18596/jotcsa.440080

Abstract

In this study, some new 5-substituted bis-iminothiazolidinone derivatives have been synthesized via one-pot green synthesis. The study comprises two steps. In the first step, bis-thioureas were prepared by the reaction of aryl isothiocyanates with substituted amines. In the second step, substituted bis-thioureas prepared beforehand and chloroacetic acid were condensed with substituted thiophene-2-carboxaldehydes and new 5-substituted bis-iminothiazolidinone compounds were obtained. The structures of all these synthesized compounds were determined and characterized by infrared, nuclear magnetic resonance and mass spectral data.

Keywords

bis-thiourea, 5-Substituted bis-iminothiazolidinone, one-pot reaction, green synthesis

References

• 1. Marvaniya HM, Modi KN, Sen DJ. Greener reactıons under solvent free condıtıons. International Journal of Drug Development and Research. 2011;3(2):34–44.
• 2. Sarkar A, Santra S, Kundu SK, Hajra A, Zyryanov GV, Chupakhin ON, Charushin VN, Majee A. A decade update on solvent and catalyst-free neat organic reactions: A step forward towards sustainability. Green Chemistry. 2016;18:4475–4525.
• 3. Wender PA, Handy ST, Wright DL. Towards the ideal synthesis. Chemistry and Industry. 1997;19:765–768.
• 4. Verma A, Saraf SK. 4-Thiazolidinone – A biologically active scaffold. European Journal of Medicinal Chemistry. 2008;43(5):897–905.
• 5 Edwards PJ. Thiazolidinone derivatives targeting drug - resistant lung cancer cells. Drug Discovery Today. 2008;13(23/24):1107–1108.
• 6. Gududuru V, Hurh E, Dalton JT, Miller DD. Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer. Bioorganic and Medicinal Chemistry Letter. 2004;14: 5289-5293.
• 7. Liu HL, Li Z, Anthonsen T. Synthesis and fungicidal activity of 2-imino-3-(4-arylthiazol-2-yl)-thiazolidin-4-ones and their 5-arylidene derivatives. Molecules. 2000;5(9):1055–1061.
• 8. Romine J, Martin S, Snyder L, Serrano-Wu M, Deshpande M, Whitehouse D, et al. iminothiazolidinones as inhibitors of hcv replication. Princeton, New Jersey; US 2005/0096364A. p. 57.
• 9. Hu J, Wang Y, Wei X, Wu X, Chen G, Cao G, Shen X, Zhang X, Tang Q, Liang G, Li X. Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents. European Journal of Medicinal Chemistry. 2013;64:292–301.
• 10. Kücükgüzel SG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. European Journal of Medicinal Chemistry. 2002;37(3):197–206.
• 11. Metwally MA, Farahat AA, Abdel-Wahab BF. 2-Amino-4-thiazolidinones: synthesis and reactions. Journal of Sulfur Chemistry. 2010;31(4):315-349.
• 12. Ottana R, Maccari R, Barreca ML, Bruno G, Rotondo A, Rossi A, Chiricosta G, Di Paola R, Sautebin L, Cuzzocread S, Vigoritaa MG. 5-Arylidene-2-imino-4-thiazolidinones: Design and synthesis of novel anti-inflammatory agents. Bioorganic and Medicinal Chemistry. 2005;13:4243–4252.
• 13. Chavan AA, Pai NR. Synthesis and antimicrobial screening of 5-arylidene-2-imino-4-thiazolidinones. Arkıvoc. 2007;xvi:148-155.
• 14. Zhou JF, Sun XJ, Zhu FX, Li YL, Gong GX. A Facile Synthesis of 5-Arylidene-2-imino-4-thiazolidinones under microwave irradiation. Synthetic Communications. 2008;38:4182–4187.
• 15. Khazaei A, Veisi H, Safaei M, Ahmadian H. Green synthesis of 5-arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium. Journal of Sulfur Chemistr. 2014;35(3):270–278.
• 16. Abbas N, Zaib S, Bakht SM, Ibrar A, Khan I, Batool S, Saeed A, Iqbal J. Symmetrical aryl linked bis-iminothiazolidinones as new chemical entities for the inhibition of monoamine oxidases: Synthesis, in vitro biological evaluation and molecular modelling analysis. Bioorganic Chemistry. 2017;70:17–26.
• 17. Fakhar I, Yamin BM, Hasbullah SA. Synthesis and characterization of bis-thiourea having amino acid derivatives. American Institute of Physics Conference Proceedings, 2016;1784, 030012.
• 18. Masaki M, Kitahara T, Kurita H, Ohta M. A New Method for the Removal of Chloroacetyl Groups. Journal of the American Chemical Society. 1968;90:4508-4509.
• 19. Yella R, Ghosh H, Patel BK. It is “2-imino-4-thiazolidinones” and not thiohydantoins as the reaction product of 1,3-disubstituted thioureas and chloroacetylchloride. Green Chemistry. 2008;10:1307–1312.
• 20. Bhattacharjee SK, Mukherjee R, Hazarika D, Chakraborty A, Acharjee SR. Synthesis of bioactive organosulfur compounds from phenyl isothiocyanate (PITC). Acta Ciencia Indica Chemistry. 2007;33(3):295–302.
• 21. Zhang LP, Shang XB, Wu QF, Zhang Y, Li JP. Highly efficient method for the synthesis of 1,4-phenylenedithioureas under solvent- and catalyst-free conditions promoted by microwave irradiation. Synthetic Communications. 2012;42(7),1045–1052.
• 22. Pandya D, Nair KB. Bridged bis(4-thiazolidinones) and related compounds with antibacterial activity. Pharmazie. 1993;48(6):414–17.