Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 52, 2022 - Issue 21
165
Views
1
CrossRef citations to date
0
Altmetric
Articles

Synthesis of novel 4-thiazolidinone derivatives via one-pot three-component reaction of maleimide, thiosemicarbazide, and Meldrum’s acid

, , , &
Pages 2019-2028 | Received 30 Mar 2022, Published online: 22 Sep 2022

References

  • Young, D. W. Heterocyclic Chemistry, 1st ed.; Longman Group Ltd: London, 1975.
  • Naeem, M.; Chuudhary, M. N.; Baloch, I. H. Greener Approach to the Synthesis of 4-Thiazolidinone Derivatives Using Phase Transfer Catalysts under Microwave Irradiation. J. Chem. Soc. Pak. 2009, 31, 633–637.
  • Sharma, M. C.; Sahu, N. K.; Kohali, D. V.; Chaturvedi, S. C.; Sharma, S. QSAR, Synthesis and Biological Activity Studies of Some Thiazolidinones Derivatives. Dig. J. Nanomater. Biostruct. 2009, 4, 223–232.
  • Mahmoud, H. K.; Abbas, A. A.; Gomha, S. M. Synthesis, Antimicrobial Evaluation and Molecular Docking of New Functionalized Bis(1,3,4-Thiadiazole) and Bis(Thiazole) Derivatives. Polycycl. Aromat. Comp. 2019, 41, 1–13. DOI: 10.1080/10406638.2019.1709085.
  • Gadre, J. N.; Nair, S.; Chitre, S. Synthesis of Some New 4-Thiazolidinones and Thiazin-4-Ones as Biologically Potent Agents. Indian J. Chem. B Org. Med. Chem. 2007, 46, 653–659.
  • Patel, R. B.; Desai, P. S.; Desai, K. R.; Chikhalia, K. H. Synthesis of Pyrimidine Based Thiazolidinones and Azetidinones: Antimicrobial and Antitubercular Agents. Chem. Inform. 2006, 45B, 773–778. DOI: 10.1002/chin.200628143.
  • Kishore, A.; Nampurath, G. K.; Mathew, S. P.; Zachariah, R. T.; Potu, B. K.; Rao, M. S.; Valiathan, M.; Chamallamudi, M. R. Antidiabetic Effect through Islet Cell Protection in Streptozotocin Diabetes, a Preliminary Assessment of Two Thiazolidin-4-Ones in Swiss Albino Mice. Chem. Biol. Interact. 2009, 177, 242–246. DOI: 10.1016/j.cbi.2008.10.032.
  • Turgut, Z.; Yolacan, C.; Aydogan, F.; Bagdatli, E.; Ocal, N. Synthesis of New Pyrazolothiazole Derivatives from 4-Thiazolidinones. Molecules 2007, 12, 2151–2159. DOI: 10.3390/12092151.
  • Mistry, K. M.; Desai, K. R. Synthesis of Novel Heterocyclic 4-Thiazolidinone Derivatives and Their Antibacterial Activity. Eur. J. Chem. 2004, 1, 189–193. DOI: 10.1155/2004/590439.
  • Kucukguzel, S. G.; Oruc, E. E.; Rollas, S.; Sahin, F.; Ozbek, A. Synthesis, Characterisation and Biological Activity of Novel 4-Thiazolidinones, 1,3,4-Oxadiazoles and Some Related Compounds. Eur. J. Med. Chem. 2002, 37, 197–206. DOI: 10.1016/S0223-5234(01)01326-5.
  • Taranalli, A. D.; Bhat, A. R.; Srinivas, S.; Saravanan, E. Antiinflammatory, Analgesic and Antipyretic Activity of Certain Thiazolidinones. Indian J. Pharm. Sci. 2008, 70, 159–164. DOI: 10.4103/0250-474X.41448.
  • Shah, V.; Pant, C. K.; Joshi, J. Synthesis and Antifungal Activity of Some Bis(2-Arylimino- 3-Yl-Thiazolidinones) and Bis-(1-Aryl-3-Yl-2-Thiohydantoins). Asian J. Chem. 1993, 5, 83–88.
  • Gomha, S. M.; Abdelhady, H. A.; Hassain, D. Z. H.; Abdelmonsef, A. A. H.; El-Naggar, M.; Elaasser, M. E.; Mahmoud, H. K. Thiazole-Based Thiosemicarbazones: Synthesis, Cytotoxicity Evaluation and Molecular Docking Study. Drug Des. Dev. Ther. 2021, 15, 659–677. DOI: 10.2147/DDDT.S291579.
  • Gomha, S. M.; Riyadh, S. M.; Mahmmoud, E. A.; Elaasser, M. M. Synthesis and Anticancer Activity of Arylazothiazoles and 1,3,4-Thiadiazoles Using Chitosan-Grafted-Poly(4-Vinylpyridine) as a Novel Copolymer Basic Catalyst. Chem. Heterocycl. Comp. 2015, 51, 1030–1038. DOI: 10.1007/s10593-016-1815-9.
  • Gomha, S. M.; Salah, T. A.; Abdelhamid, A. O. Synthesis, Characterization, and Pharmacological Evaluation of Some Novel Thiadiazoles and Thiazoles Incorporating Pyrazole Moiety as Anticancer Agents. Monatsh Chem. 2015, 146, 149–158. DOI: 10.1007/s00706-014-1303-1309.
  • Ramalakshmi, N.; Aruloly, L.; Subramani, A.; Ilango, K.; Puratchikody, A. Synthesis and Biological Evaluation of Some Novel Nicotinic Acid Derivatives. Malays. J. Sci. 2009, 28, 197–203. DOI: 10.22452/mjs.vol28no2.8.
  • Dawood, K. M.; Gomha, S. M. Synthesis and Anti-Cancer Activity of 1,3,4-Thiadiazole and 1,3-Thiazole Derivatives Having 1,3,4-Oxadiazole Moiety. J. Heterocycl. Chem. 2015, 52, 1400–1405. DOI: 10.1002/jhet.2250.
  • Holota, S.; Kryshchyshyn, A.; Derkach, H.; Trufin, Y.; Demchuk, I.; Gzella, A.; Grellier, P.; Lesyk, R. Synthesis of 5-Enamine-4-Thiazolidinone Derivatives with Trypanocidal and Anticancer Activity. Bioorg. Chem. 2019, 86, 126–136. DOI: 10.1016/j.bioorg.2019.01.045.
  • Ouf, S. A.; Gomha, S. M.; Ewies, M. M.; Sharawy, I. A. A. Synthesis, Characterization, and Antifungal Activity Evaluation of Some Novel Arylazothiazoles. J. Heterocycl. Chem. 2018, 55, 258–264. DOI: 10.1002/jhet.3040.
  • Vigorita, M. G.; Ottanà, R.; Monforte, F.; Maccari, R.; Trovato, A.; Monforte, M. T.; Taviano, M. F. Synthesis and Antiinflammatory, Analgesic Activity of 3,3′-(1,2-Ethanediyl)-Bis[2-Aryl-4-Thiazolidinone] Chiral Compounds. Part 10. Bioorg. Med. Chem. Lett. 2001, 11, 2791–2794. DOI: 10.1016/S0960-894X(01)00476-0.
  • Cesur, N.; Cesur, Z.; Ergenç, N.; Uzun, M.; Kiraz, M.; Kasimoğlu, O.; Kaya, D. Synthesis and Antifungal Activity of Some 2-Aryl-3-Substituted 4-Thiazolidinones. Arch. Pharm. 1994, 327, 271–3273. DOI: 10.1002/ardp.19943270414.
  • Houseknecht, K. L.; Cole, B. M.; Steele, P. J. PPAR and Its Ligands: A Review. Domest. Anim. Endocrinol. 2002, 22, 1–23. DOI: 10.1016/s0739-7240(01)00117-5.
  • Ottana, R.; MacCari, R.; Giglio, M.; Del Corso, A.; Cappiello, M.; Mura, U.; Cosconati, S.; Marinelli, L.; Novellino, E.; Sartini, S.; et al. Identification of 5-Arylidene-4-Thiazolidinone Derivatives Endowed with Dual Activity as Aldose Reductase Inhibitors and Antioxidant Agents for the Treatment of Diabetic. Eur. J. Med. Chem. 2011, 46, 2797–2806. DOI: 10.1016/j.ejmech.2011.03.068.
  • Naim, M. J.; Alam, O.; Alam, M. J.; Shaquiquzzaman, M.; Alam, M. M.; Naidu, V. J. M. Synthesis, Docking, In Vitro and In Vivo Antidiabetic Activity of Pyrazole-Based 2,4-Thiazolidinedione Derivatives as PPAR-γ Modulators. Arch. Pharm. 2018, 35, 1700223. DOI: 10.1002/ardp.201700223.
  • Umesh, R. P.; Dhanaji, V. J.; Manisha, R. B.; Ramrao, A. M. Saccharomyces cerevisiae–Catalyzed One-Pot Three-Component Synthesis of 2,3-Diaryl-4-Thiazolidinones. Tetrahedron Lett. 2011, 52, 1689–1691. DOI: 10.1016/j.tetlet.2011.01.143.
  • Vicini, P.; Geronikaki, A.; Incerti, M.; Zani, F.; Dearden, J.; Hewitt, M. 2-Heteroarylimino-5-Benzylidene-4-Thiazolidinones Analogues of 2-Thiazolylimino-5-Benzylidene-4-Thiazolidinones with Antimicrobial Activity: Synthesis and Structure–Activity Relationship. Bioorg. Med. Chem. 2008, 16, 3714–3724. DOI: 10.1016/j.bmc.2008.02.001.
  • Cunico, W.; Gomes, C. R. B.; Vellasco, W. T. Chemistry and Biological Activities of 1,3-Thiazolidin-4-Ones. MROC 2008, 5, 336–344. DOI: 10.2174/157019308786242232.
  • Havrylyuk, D.; Mosula, L.; Zimenkovsky, B.; Vasylenko, O.; Gzella, A.; Lesyk, R. Synthesis and Anticancer Activity Evaluation of 4-Thiazolidonones Containing Benzothiazol Moity. Eur. J. Med. Chem. 2010, 45, 5012–5021. DOI: 10.1016/j.ejmech.2010.08.008.
  • Murata, T.; Murai, M.; Ikeda, Y.; Miki, K.; Ohe, K. Pd-and Cu-Catalyzed One-Pot Multicomponent Synthesis of Hetero α,α′-Dimers of Heterocycles. Org. Lett. 2012, 14, 2296–2299. DOI: 10.1021/ol300718x.
  • Sadou, N.; Aichouche-Bouzroura, S.; Nechak, R.; Nedjar-Kolli, B.; Morizur, V.; Poulain-Martini, S.; Dunach, E. Acid-Catalyzed Synthesis of Thiazolidin-4-Ones. Polycycl. Aromat. Compd. 2018, 38, 311–321. DOI: 10.1080/10406638.2016.1207685.
  • Nechak, R.; Bouzroura, S. A.; Benmalek, Y.; Salhi, L.; Martini, S. P.; Morizur, V.; Dunach, E.; Kolli, B. N. Synthesis and Antimicrobial Activity Evaluation of Novel 4-Thiazolidinones Containing a Pyrone Moiety. Synth. Commun. 2015, 45, 262–272. DOI: 10.1080/00397911.2014.970278.
  • Nechak, R.; Achouche Bouzroura, S.; Benmalek, Y.; Boufroua, N.; Nedjar Kolli, B.; Poulain Martini, S.; Duñach, E. Synthesis, Identification and Antimicrobial Activity of Substituted Thiazolines and 1,3,4-Thiadiazines from Dehydroacetic Acid. Synth. Commun. 2019, 49, 1895–1905. DOI: 10.1080/00397911.2019.1606918.
  • Salhi, L.; Achouche-Bouzroura, S.; Nechak, R.; Nedjar-Kolli, B.; Rabia, C.; Merazig, H.; Poulain-Martini, S.; Dunach, E. Synthesis of Functionalized Dihydroimidazo[1,2-a]Pyridines and 4-Thiazolidinone Derivatives from Maleimide, as New Class of Antimicrobial Agents. Synth. Commun. 2020, 50, 412–422. DOI: 10.1080/00397911.2019.1699933.
  • Bremner, W. S.; Organ, M. G. Multicomponent Reactions to Form Heterocycles by Microwave-Assisted Continuous Flow Organic Synthesis. J. Comb. Chem. 2007, 9, 14–16. DOI: 10.1021/cc060130p.
  • Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Strategies for Heterocyclic Construction via Novel Multicomponent Reactions Based on Isocyanides and Nucleophilic Carbenes. Acc. Chem. Res. 2003, 36, 899–907. DOI: 10.1021/ar020258p.
  • Asghari, S.; Pourshab, M.; Mohseni, M. Synthesis, Characterization, and Evaluation of Antioxidant and Antibacterial Activities of Novel Indole-Hydrazono Thiazolidinones. Monatsh Chem. 2018, 149, 2327–2336. DOI: 10.1007/s00706-018-2292-x.
  • Sayed, A. R.; Gomha, S. M.; Taher, E. A.; Muhammad, Z. A.; El-Seedi, H. R.; Gaber, H. M.; Ahmed, M. M. One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents. Drug Des. Dev. Ther. 2020, 14, 1363–1375. DOI: 10.2147/dddt.s221263.
  • Bose Subhas, D.; Ramesh, N. A Convenient Access to 2,4-Disubstituted Quinazolines via One-Pot Three-Component Reaction under Mild Conditions. Synth. Commun. 2020, 50, 1495–1503. DOI: 10.1080/00397911.2020.1744014.
  • Yang, L.; Wan, J.-P. Ethyl Lactate Participated Three-Component Dehydrogenative Reactions: biomass Feedstock in Diversity Oriented Quinoline Synthesis. Green Chem. 2020, 22, 3074–3078. DOI: 10.1039/D0GC00738B.
  • Teimouri, M. B.; Yousefi, S.; Meydani, A. One-Pot Three-Component Synthesis of a New Series of Tetrahydrobenzofuran-Chromone Conjugates. Synth. Commun. 2021, 51, 1974–1981. DOI: 10.1080/00397911.2021.1918169.
  • Guo, H.; Tian, L.; Liu, Y.; Wan, J.-P. DMSO as a C1 Source for [2 + 2 + 1] Pyrazole Ring Construction via Metal-Free Annulation with Enaminones and Hydrazines. Org. Lett. 2022, 24, 228–233. DOI: 10.1021/acs.orglett.1c03879.
  • McNab, H. Meldrum’s Acid. Chem. Soc. Rev. 1978, 7, 345–358. DOI: 10.1039/cs9780700345.
  • Chen, B. C. Meldrum’s Acid in Organic Synthesis. Heterocycles 1991, 32, 529–597. DOI: 10.3987/REV-90-422.
  • Gerencsér, J.; Dormán, G.; Darvas, F. Meldrum’s Acid in Multicomponent Reactions: Applications to Combinatorial and Diversity-Oriented Synthesis. QSAR Comb. Sci. 2006, 25, 439–448. DOI: 10.1002/qsar.200540212.
  • Ramachary, D. B.; Barbas, C. F. Towards Organo-Click Chemistry: Development of Organocatalytic Multicomponent Reactions through Combinations of Aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen Cycloaddition Reactions. Chemistry 2004, 10, 5323–5331. DOI: 10.1002/chem.200400597.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.