Synthesis of Multifunctionalized 2-Iminothiazolidin-4-ones and Their 2-Arylimino Derivatives

Abstract

Multifunctionalized 2-imino-3-(pyrazol-4-yl)thiazolidin-4-ones and 2-arylimino-3-(pyrazol-4-yl)thiazolidin-4-ones were prepared according to an efficient four-step procedure. The key step of the synthetic pathway involved the cyclization of 2-chloro-N-(pyrazol-4-yl)acetamide intermediate using KSCN or aryl isothiocyanate, respectively. The structure of the title compounds was confirmed on the basis of NMR data and ¹⁵N-labeling.

Key words

thiazolidin-4-ones - pyrazoles - cyclization - heterocycles - regioselectivity

• References

• 1 Verma A, Saraf SK. Eur. J. Med. Chem. 2008; 43: 897
• 2 Brown FC. Chem. Rev. 1961; 61: 463
• 3 Lesyk RB, Zimenkovsky BS. Curr. Org. Chem. 2004; 8: 1547
• 4 Liu HL, Li Z, Anthonsen T. Molecules 2000; 5: 1055
• 5 Lakhan R. Agric. Biol. Chem. 1982; 46: 557
• 6 Aschale M, Akhtar RS, Ayalew A, Upadhyay RK. Int. J. Curr. Chem. 2011; 2: 189
• 7 Ottanà R, Maccari R, Barreca ML, Bruno G, Rotondo A, Rossi A, Chiricosta G, Di Paola R, Sautebin L, Cuzzocrea S, Vigorita MG. Bioorg. Med. Chem. 2005; 13: 4243
• 8 Ma L, Pei H, Lei L, He L, Chen J, Liang X, Peng A, Ye H, Xiang M, Chen L. Eur. J. Med. Chem. 2015; 92: 178
• 9 Dwivedi C, Gupta SS, Parmar J. J. Med. Chem. 1972; 15: 553
• 10 Amin KM, Rahman DE. A, Al-Eryani YA. Bioorg. Med. Chem. 2008; 16: 5377
• 11 Chaudhary M, Parmar SS, Chaudhary SK, Chaturvedi AK, Ramasastry BV. J. Pharm. Sci. 1976; 65: 443
• 12 Shehab WS, Mouneir SM. Eur. J. Chem. 2015; 6: 157
• 13 Eicher T, Hauptmann S, Speicher A. The Chemistry of Heterocycles . 2nd ed. Wiley; New York: 2004: 179
• 14 Güniz Küçükgüzel S, Senkardes S. Eur. J. Med. Chem. 2015; 97: 786
• 15 Le Corre L, Tak-Tak L, Guillard A, Prestat G, Gravier-Pelletier C, Busca P. Org. Biomol. Chem. 2015; 13: 409
• 16 Sarkis M, Tran DN, Kolb S, Miteva MA, Villoutreix BO, Garbay C, Braud E. Bioorg. Med. Chem. Lett. 2012; 22: 7345
• 17 Havrylyuk D, Roman O, Lesyk R. Eur. J. Med. Chem. 2016; 113: 145
• 18 Moghaddam FM, Hojabri L. J. Heterocycl. Chem. 2007; 44: 35
• 19 Zheng W, Degterev A, Hsu E, Yuan J, Yuan C. Bioorg. Med. Chem. Lett. 2008; 18: 4932
• 20 Saravanan G, Selvaraju R, Nagarajan S. Synth. Commun. 2012; 42: 3361
• 21 El-Mariah F. Phosphorus, Sulfur, Silicon Relat. Elem. 2008; 183: 2795
• 22 Hanefeld W, Schlitzer M. J. Heterocycl. Chem. 1994; 31: 391
• 23 Abdillahi I, Revelant G, Datoussaid Y, Kirsch G. Synthesis 2010; 2543
• 24 Vicini P, Geronikaki A, Incerti M, Zani F, Dearden J, Hewitt M. Bioorg. Med. Chem. 2008; 16: 3714
• 25 Chawla P, Singh R, Saraf SK. Med. Chem. Res. 2011; 21: 3263
• 26 Ostapiuk YV, Obushak MD, Matiychuk VS, Naskrent M, Gzella AK. Tetrahedron Lett. 2012; 53: 543
• 27 Géci I, Imrich J, Kristian P, Kivelä H, Valtamo P, Pihlaja K. J. Heterocycl. Chem. 2005; 42: 907
• 28 Revelant G, Hesse S, Kirsch G. Synthesis 2010; 3319
• 29 Bolli MH, Abele S, Binkert C, Bravo R, Buchmann S, Bur D, Gatfield J, Hess P, Kohl C, Mangold C, Mathys B, Menyhart K, Müller C, Nayler O, Scherz M, Schmidt G, Sippel V, Steiner B, Strasser D, Treiber A, Weller T. J. Med. Chem. 2010; 53: 4198
• 30 Sarkis M, Tran DN, Dasso Lang MC, Garbay C, Braud E. Synlett 2014; 25: 1257
• 31 El’tsov OS, Mokrushin VS, Bel’skaya NP, Kozlova NM. Russ. Chem. Bull. 2003; 52: 461
• 32 Urbano M, Guerrero M, Velaparthi S, Crisp M, Chase P, Hodder P, Schaeffer MT, Brown S, Rosen H, Roberts E. Bioorg. Med. Chem. Lett. 2011; 21: 6739
• 33 Jalani HB, Pandya AN, Pandya DH, Sharma JA, Sudarsanam V, Vasu KK. Tetrahedron Lett. 2013; 54: 5403
• 34 Munch H, Hansen JS, Pittelkow M, Christensen JB, Boas U. Tetrahedron Lett. 2008; 49: 3117
• 35 Zhang Z, Daynard TS, Chafeev MA, Wang S, Chopiuk GB, Sviridov SV. Patent WO 2003045379, 2003
• 36 Al-Matar H, Mohamed K, Khaled D, Al-Dorri DM, Elnagdi MH. Molecules 2010; 15: 3302
• 37 Zhu X, Chen Y, Chen Y, Wang J, Su W. Lett. Org. Chem. 2014; 11: 621
• 38 Jacq J, Pasau P. Chem. Eur. J. 2014; 20: 12223
• 39 Simova S, Radeglia R, Fanghaenel E. J. Prakt. Chem. 1983; 325: 863