173
Views
10
CrossRef citations to date
0
Altmetric
Articles

Microwave-assisted one-pot three-component synthesis of thiazolidinones using KSF@Ni as an efficient heterogeneous catalyst

, &
Pages 668-678 | Received 01 Dec 2016, Accepted 12 Jun 2017, Published online: 26 Jun 2017

References

  • De Monte C, Carradori S, Bizzarri B, et al. Anti-Candida activity and cytotoxicity of a large library of new N-substituted-1,3-thiazolidin-4-one derivatives. Eur J Med Chem. 2016;107:82–96. doi: 10.1016/j.ejmech.2015.10.048
  • Sharath Kumar KS, Hanumappa A, Vetrivel M, et al. Antiproliferative and tumor inhibitory studies of 2,3 disubstituted 4-thiazolidinone derivatives. Bioorg Med Chem Lett. 2015;25(17):3616–3620. doi: 10.1016/j.bmcl.2015.06.069
  • Bhosle MR, Mali JR, Pal S, et al. Synthesis and antihyperglycemic evaluation of new 2-hydrazolyl-4-thiazolidinone-5-carboxylic acids having pyrazolyl pharmacophores. Bioorg Med Chem Lett. 2014;24:2651–2654. doi: 10.1016/j.bmcl.2014.04.064
  • Kunzler A, Neuenfeldt PD, das Neves AM, et al. Synthesis, antifungal and cytotoxic activities of 2-aryl-3-((piperidin-1-yl)ethyl)thiazolidinones. Eur J Med Chem. 2013;64:74–80. doi: 10.1016/j.ejmech.2013.03.030
  • Tenório RP, Carvalho CS, Pessanha CS, et al. Synthesis of thiosemicarbazone and 4-thiazolidinone derivatives and their in vitro anti-Toxoplasma gondii activity. Bioorg Med Chem Lett. 2005;15:2575–2578. doi: 10.1016/j.bmcl.2005.03.048
  • Omar K, Geronikaki A, Zoumpoulakis P, et al. Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg Med Chem. 2010;18:426–432. doi: 10.1016/j.bmc.2009.10.041
  • Rahim F, Zaman K, Ullah H, et al. Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents. Bioorg Chem. 2015;63:123–131. doi: 10.1016/j.bioorg.2015.10.005
  • Rao A, Chimirri A, Ferro S, et al. Microwave-assisted synthesis of benzimidazole and thiazolidinone derivatives as HIV-1 RT inhibitors. Arkivoc. 2004;5:147–155.
  • Taha HA, Soliman MI. Antischistosomal activity of 3-substituted-5-(2-aryl-2-oxoethyl)-2,4-dioxo-1,3-thiazolidine. Int J Agri Biol. 2007;1:87–93.
  • Kristina MO, Melissa RM, Gutierrez-de-Teran H, et al. α-Substituted norstatines as the transition-state mimic in inhibitors of multiple digestive vacuole malaria aspartic proteases. Bioorg Med Chem. 2009;17:5933–5949. doi: 10.1016/j.bmc.2009.06.065
  • Sanemitsu Y, Kawamura S, Satoh J, et al. Synthesis and herbicidal activity of 2-acylimino-3-phenyl-1,3-thiazolines – a new family of bleaching herbicides. J Pestic Sci. 2006;31(3):305–310. doi: 10.1584/jpestics.31.305
  • Murugan R, Anbazhagan S, Narayanan SS. Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3 + 2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives. Eur J Med Chem. 2009;44:3272–3279. doi: 10.1016/j.ejmech.2009.03.035
  • Secci D, Carradori S, Bizzarri B, et al. Novel 1,3-thiazolidin-4-one derivatives as promising anti-Candida agents endowed with anti-oxidant and chelating properties. Eur J Med Chem. 2016;117:144–156. doi: 10.1016/j.ejmech.2016.04.012
  • Pizzo C, Saiz C, Talevi A, et al. Synthesis of 2-hydrazolyl-4-thiazolidinones based on multicomponent reactions and biological evaluation against Trypanosoma Cruzi. Chem Biol Drug Des. 2011;77:166–172. doi: 10.1111/j.1747-0285.2010.01071.x
  • Blanchet J, Zhu J. Reeve's synthesis of 2-imino-4-thiazolidinone from alkyl (aryl) trichloromethylcarbinol revisited, a three-component process from aldehyde, chloroform and thiourea. Tetrahedron Lett. 2004;45:4449–4452. doi: 10.1016/j.tetlet.2004.04.055
  • Dandia A, Singh R, Bhaskaran S, et al. Versatile three component procedure for combinatorial synthesis of biologically relevant scaffold spiro[indole-thiazolidinones] under aqueous conditions. Green Chem. 2011;13:1852–1859. doi: 10.1039/c0gc00863j
  • Li JP, Zheng PZ, Liu RJ, et al. A facile synthesis of thiosemicarbazides containing the 4-antipyrinyl group under microwave irradiation in solvent-free conditions. J Sulfur Chem. 2005;27:169–174. doi: 10.1080/17415990600570852
  • Li Y, Wang Y, Li J, et al. Regioselective synthesis of 1-aryl-2-p-toluenesulfonyl hydrazides under microwave irradiation. J Sulfur Chem. 2007;28:177–180. doi: 10.1080/17415990701209590
  • Dandia A, Sati M, Arya K, et al. Green chemical approach for facile one-pot synthesis of 2,4,8-trisubstituted-1,5-benzothiazepines and their dioxides under microwave irradiation. J Sulfur Chem. 2004;25:283–289. doi: 10.1080/17415990412331282468
  • Sharifi Aliabadi R, Mahmoodi NO. Green and efficient synthesis of pyranopyrazoles using [bmim][OH−] as an ionic liquid catalyst in water under microwave irradiation and investigation of their antioxidant activity. RSC Adv. 2016;6:85877–85884. doi: 10.1039/C6RA17594E
  • Bigi F, Chesini L, Maggi R, et al. Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids. J Org Chem. 1999;64:1033–1035. doi: 10.1021/jo981794r
  • Chankeshwara SV, Chakraborti AK. Montmorillonite K 10 and montmorillonite KSF as new and reusable catalysts for conversion of amines to N-tert-butylcarbamates. J Mol Cat A: Chemical. 2006;253:198–202. doi: 10.1016/j.molcata.2006.03.042
  • Shao LX, Shi M. Montmorillonite KSF-catalyzed one-pot, three-component, Aza-Diels–Alder reactions of methylenecyclopropanes with arenecarbaldehydes and arylamines. Adv Syn Cat. 2003;345:963–966. doi: 10.1002/adsc.200303057
  • Li TS, Zhang ZH, Yang F. Montmorillonite clay catalysis. Part 7.1 an environmentally friendly procedure for the synthesis of coumarins via pechmann condensation of phenols with ethyl acetoacetate. J Chem Res. 1998;0:38–39. doi: 10.1039/a703694i
  • Habibi D, Marvi O. Montmorillonite KSF clay as an efficient catalyst for the synthesis of 1,4-dioxo-3,4-dihydrophthalazine-2(1H)-carboxamides and -carbothioamides under solvent-free conditions using microwave irradiation. Catal Commun. 2007;8:127–130. doi: 10.1016/j.catcom.2006.05.004
  • Nikpassand M, Mamaghani M, Tabatabaeian K, et al. KSF: an efficient catalyst for the regioselective synthesis of 1,5-diaryl pyrazoles using Baylis–Hillman adducts. Mol Divers. 2009;13:389–393. doi: 10.1007/s11030-009-9123-2
  • Ghanbari Pirbasti F, Mahmoodi NO. Facile synthesis and biological assays of novel 2,4-disubstituted hydrazinyl-thiazoles analogs. Mol Divers. 2016;20:497–506. doi: 10.1007/s11030-015-9654-7
  • Mahmoodi NO, Khalili B, Rezaeianzade O, et al. One-pot multicomponent synthesis of indol-3-yl-hydrazinyl thiazoles as antimicrobial agents. Res Chem Intermed. 2016;42:6531–6542. doi: 10.1007/s11164-016-2478-y
  • Mahmoodi NO, Ramzanpour S, Ghanbari Pirbasti F. One-pot multi-component synthesis of 1,4-dihydropyridines using Zn2+@KSF and evaluating their antibacterial and antioxidant activities. Arch Pharm. 2015;348:275–282. doi: 10.1002/ardp.201400414
  • Mahmoodi NO, Shoja S, Tabatabaeian K, et al. Ultrasound-promoted one-pot five-components synthesis of biologically active novel bis((6-alkyl or phenyl-2-phenylpyrimidine-4-yl) oxy) alkane or methyl benzene derivatives. Ultrason Sonochem. 2015;23:31–36. doi: 10.1016/j.ultsonch.2014.09.001
  • Mahmoodi NO, Nikokar I, Farhadi M, et al. One-pot multi-component synthesis of mono- and bis-indolylimidazole derivatives using Zn2+@KSF and their antibacterial activity. Z Naturforsch B. 2014;69:715–720. doi: 10.5560/znb.2014-4026
  • Mahmoodi NO, Shoja S, Sharifzadeh B, et al. Regioselective synthesis and antibacterial evaluation of novel bis-pyrimidine derivatives via a three-component reaction. Med Chem Res. 2014;23:1207–1213. doi: 10.1007/s00044-013-0731-0
  • Sharifzadeh B, Mahmoodi NO, Mamaghani M, et al. Facile regioselective synthesis of novel bioactive thiazolyl-pyrazoline derivatives via a three-component reaction and their antimicrobial activity. Bioorg Med Chem Lett. 2013;23:548–551. doi: 10.1016/j.bmcl.2012.11.024
  • Mahmoodi NO, Zanjanchi MA, Aliakbar A, et al. Synthesis of novel symmetric schiff bases using KSF. Orient J Chem. 2011;27:517–522.
  • Zare L, Mahmoodi NO, Yahyazadeh A, et al. An efficient chemo- and regioselective three-component synthesis of pyridazinones and phthalazinones using activated KSF. Chin Chem Lett. 2010;21:538–541. doi: 10.1016/j.cclet.2009.11.032
  • Xu Z, Yu J, Liu G, et al. Microemulsion-assisted synthesis of hierarchical porous Ni(OH)2/SiO2 composites toward efficient removal of formaldehyde in air. Dalton Trans. 2013;42:10190–10197. doi: 10.1039/c3dt51067k
  • Ul-Hamid A, Quddus A, Saricimen H, et al. Corrosion behavior of coarse- and fine-grain Ni coatings incorporating NaH2PO4·H2O inhibitor treated substrates. Mater Res. 2015;18:20–26. doi: 10.1590/1516-1439.253114
  • Hall DS, Lockwood DJ, Bock C, et al. You have access Nickel hydroxides and related materials: a review of their structures, synthesis and properties. Proc R Soc A. 2015;471:792–857.
  • Saiz C, Pizzo C, Manta E, et al. Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones. Tetrahedron Lett. 2009;50:901–904. doi: 10.1016/j.tetlet.2008.12.020
  • Shanbhag GV, Halligudi SB. Intermolecular hydroamination of alkynes catalyzed by zinc-exchanged montmorillonite clay. J Mol Catal A: Chem. 2004;222:223–228. doi: 10.1016/j.molcata.2004.08.010

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.