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Environmentally Benign Synthesis of 4-Thiazolidinone Derivatives Using a Co/Al Hydrotalcite as Heterogeneous Catalyst

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Abstract

The present effort describes facile and environmentally benign synthesis of 4-thiazolidinone via oxidative cyclocondensation of benzyl alcohols, various substituted aromatic anilines and thioglycolic acid using a Co-Al hydrotalcite based heterogeneous catalyst (Co@HT) in methanol act as a solvent. We have synthesized three types of Co@HT with different molar ratio Co@HT-2 (1:1), Co@HT-3 (2:1), Co@HT-4 (3:1). Characterization of synthesized Co@HT catalyst using various analysis techniques such as FT-IR, powder XRD, SEM, XPS, EDS, DTG-TGA and N2 physical adsorption. Among the synthesized hydrotalcite, Co-HT-3 exhibit admirable catalytic activity towards oxidation of benzyl alcohol followed by cyclocondensation of respective aldehydes, anilines and thioglycolic acid into the corresponding 4-thiazolidinones in methanol at 60 οC using O2 as a oxidant. Furthermore, after end of the reaction, the catalyst is easily recovered and eco-friendly without any considerable loss in its catalytic efficiency.

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References

  1. Rotstein BH, Zaretsky S, Rai V, Yudin AK (2014) Chem Rev 114:8323 and references cited therein

  2. Domling A, Wang W, Wang K (2012) Chem Rev 112:3083 and references cited therein

  3. Sheldon RA (2000) Pure Appl Chem 72:1233

    CAS  Google Scholar 

  4. Amin KM, Rahman DE, Al-Eryani YA (2008) Bioorg Med Chem 16:5377

    CAS  PubMed  Google Scholar 

  5. Barreca ML, Chimirri A, De Luca L, Monforte AM, Monforte P, Rao A, Zappala M, Balzarini J, De Clercq E, Pannecouque C, Witvrouw M (2001) Bioorg Med Chem Lett 11:1793

    CAS  PubMed  Google Scholar 

  6. Pansare DN, Mulla NA, Pawar CD, Shende VR, Shinde DB (2014) Bioorg Med Chem Lett 24:3569

    CAS  PubMed  Google Scholar 

  7. Vigorita MG, Ottana R, Monforte F, Maccari R, Trovato A, Monforte MT, Taviano MF (2001) Bioorg Med Chem Lett 11:2791

    CAS  PubMed  Google Scholar 

  8. Ottana R, Maccari R, Giglio M, Del Corso A, Cappiello M, Mura U, Cosconati S, Marinelli L, Novellino E, Sartini S, La Motta C, Da Settimo F (2011) Eur J Med Chem 46:2797

    CAS  PubMed  Google Scholar 

  9. Kothanahally S, Sharath K, Ananda H, Maruthai V, Mahesh H, Yarabhally RG, Thinnali RB, Suguna R, Sathees CR, Kanchugarakoppal SR (2015) Bioorg Med Chem Lett 25:3616

    Google Scholar 

  10. Carlson EE, May JF, Kiessling LL (2006) Chem Biol 13:825

    CAS  PubMed  Google Scholar 

  11. Subhedar DD, Shaikh MH, Arkile M, Yeware A, Sarkar D, Shingate BB (2016) Bioorg Med Chem Lett 26:1704

    CAS  PubMed  Google Scholar 

  12. Taranalli AD, Thimmaiah NV, Srinivas S, Saravanan EA (2009) J Pharm Clin Res 2:79

    CAS  Google Scholar 

  13. Panico AM, Vicini P, Geronikaki A, Incerti M, Cardile V, Crasci L, Messina R, Ronsisvalle S (2011) Bioorg Chem 39:48

    CAS  PubMed  Google Scholar 

  14. Mazzoni O, di Bosco AM, Grieco P, Novellino E, Bertamino A, Borrelli F, Capasso R, Diurno MV (2006) Chem Biol Drug Des 67:432

    CAS  PubMed  Google Scholar 

  15. Maria L, Barreca AC, Laura DL, Anna-Maria M, Pietro M, Angela R, Maria Z, Jan B, Erik DC, Christophe P, Myriam W (2001) Bioorg Med Chem Lett 11:1793

    Google Scholar 

  16. Bhandari SV, Bothara KG, Patil AA, Chitre TS, Sarkate AP, Gore ST, Dangre SC, Khachane CV (2009) Bioorg Med Chem 17:390

    CAS  PubMed  Google Scholar 

  17. Wrobel J, Jetter J, Kao W, Rogers J, Di L, Chi J, Perez MC, Chen GC, Shen ES (2006) Bioorg Med Chem 14:5729

    CAS  PubMed  Google Scholar 

  18. Sala M, Chimento A, Saturnino C, Gomez-Monterrey IM, Musella S, Bertamino A, Milite C, Sinicropi MS, Caruso AR, Sirianni P, Tortorella E, Novellino P, Campiglia Pezzi V (2013) Bioorg Med Chem Lett 23:4990

    CAS  PubMed  Google Scholar 

  19. Carter PH, Scherle PA, Muckelbauer JA, Voss ME, Liu RQ, Thompson LA, Tebben AJ, Solomon KA, Lo YC, Li Z, Strzemienski P, Yang G, Falahatpisheh N, Xu M, Wu Z, Farrow NA, Ramnarayan K, Wang J, Rideout D, Yalamoori V, Domaille P, Underwood DJ, Trzaskos JM, Friedman SM, Newton RC, Decicco CP (2001) Proc Natl Acad Sci U S A 98:11879

    CAS  PubMed  PubMed Central  Google Scholar 

  20. Cutshall NS, O’Day C, Prezhdo M (2005) Bioorg Med Chem Lett 15:3374

    CAS  PubMed  Google Scholar 

  21. Dayam R, Aiello F, Deng J, Wu Y, Garofalo A, Chen X, Neamati N (2006) J Med Chem 49:4526

    CAS  PubMed  Google Scholar 

  22. Degterev A, Lugovskoy A, Cardone M, Mulley B, Wagner G, Mitchison T, Yuan J (2001) Nat Cell Biol 3:173

    CAS  PubMed  Google Scholar 

  23. Kumar KSS, Hanumappa A, Vetrivel M, Hegde M, Girish YR, Byregowda TR, Rao S, Raghavan SC, Rangappa KS (2015) Bioorg Med Chem Lett 25:3616

    Google Scholar 

  24. Ottana R, Carotti S, Maccari R, Landini I, Chiricosta G, Caciagli B, Vigorita MG, Mini E (2005) Bioorg Med Chem Lett 15:3930

    CAS  PubMed  Google Scholar 

  25. Chen S, Chen L, Le NT, Zhao C, Sidduri A, Lou JP, Michoud C, Portland L, Jackson N, Liu JJ, Konzelmann F, Chi F, Tovar C, Xiang Q, Chen Y, Wen Y, Vassilev LT (2007) Bioorg Med Chem Lett 17:2134

    CAS  PubMed  Google Scholar 

  26. Debecker DP, Gaigneaux EM, Busca G (2009) Chem-Eur J 15:3920

    CAS  PubMed  Google Scholar 

  27. Massah AR, Kalabashi RJ, Toghiani M, Hojati B, Adibnejad M (2012) Euro Jour of Chemy 9:2501

    CAS  Google Scholar 

  28. Climent MJ, Corma A, Iborra S, Velty A (2004) J Catal 221:474

    CAS  Google Scholar 

  29. Pavel OD, Cojocaru B, Angelescu E, Parvulescu VI (2011) Appl Catal a-Gen 403:83

    CAS  Google Scholar 

  30. Subhedar DD, SSR G, Bhanage (2018) BM Catalysis Letters 148:3102

    CAS  Google Scholar 

  31. Raut AB, Bhanage BM (2018) Chem Select 3:11388

    CAS  Google Scholar 

  32. Jadhav VH, Dumbre DK, Phapale VB, Borate HB, Wakharkar RD (2007) Catal Commun 8:65

    CAS  Google Scholar 

  33. Cantrell DG, Gillie LJ, Lee AF, Wilson K (2005) Appl Catal a-Gen 287:183

    CAS  Google Scholar 

  34. Baskaran T, Kumaravel R, Christopher J, Sakthivel A (2014) RSC Adv 4:11188

    CAS  Google Scholar 

  35. Thakare MP, Kumar P, Kumar N, Pandey SK (2014) Tetrahedron Lett 55:2463

    CAS  Google Scholar 

  36. Azgomi N, Mokhtary M (2015) J Mol Cat Chem 398:58

    CAS  Google Scholar 

  37. Sharma R, Veera G, Devi B, Reddy KS, Reddy MV, Kondapi AK, Bhaskar C (2015) Hetero Commun 21:187

    Google Scholar 

  38. Prasad D, Preetam A, Nath M (2012) RSC Adv 2:3133

    CAS  Google Scholar 

  39. Vasincu IM, Apotrosoaei M, Panzariu AT, Buron F, Routier S, Profire L (2014) Molecules 19:15005

    PubMed  PubMed Central  Google Scholar 

  40. Liaras K, Fesatidou M, Geronikaki A (2018) Molecules 23:685

    PubMed Central  Google Scholar 

  41. Apotrosoaei M, Vasincu IM, Dragan M, Buron F, Routier S, Profire L (2014) Molecules 19:13824

    PubMed  PubMed Central  Google Scholar 

  42. Ghomi JS, Navvab M, Alavi HS (2015) Ultrason Sonochem 31:102

    Google Scholar 

  43. Ebrahimi S (2016) J Sulfur Chem 37:587

    CAS  Google Scholar 

  44. Sadou N, Bouzroura SA, Nechak R, Kolli BN, Morizur V, Martini SP, Dunach E (2016) Polycycl Aromat Compd 36:1

    Google Scholar 

  45. Foroughifar N, Ebrahimi S (2013) Chin Chem 24:389

    CAS  Google Scholar 

  46. Gautam D, Gautam P, Chaudhary RP (2012) Chin Chem Lett 23:1221

    CAS  Google Scholar 

  47. Mamaghani M, Pourranjbar M, Nia RH (2014) J Sulfur Chem 35:1

    CAS  Google Scholar 

  48. Ghomi JS, Navvab M, Alavi HS (2016) J Sulfur Chem 37:601

    Google Scholar 

  49. Luo J, Zhong Z, Ji H, Chen J, Zhao J, Zhang F (2016) J Sulfur Chem 37:438

    CAS  Google Scholar 

  50. Gupta SSR, Nakhate AV, Rasal KB, Deshmukh GP, Mannepalli LK (2017) New J Chem 4:15268

    Google Scholar 

  51. Yu JJ, Jiang Z, Zhu L, Hao ZP, Xu ZP (2006) J Phys Chem B 110:4291

    CAS  PubMed  Google Scholar 

  52. Perez-Ramırez J, Mul G, Moulijn J (2001) Vib Spectrosc 27:75

    Google Scholar 

  53. Guo J, Lou H, Zhao H, Chai D, Zheng X (2004) Appl Catal A 273:75

    CAS  Google Scholar 

  54. Carpentier J, Lamonier JF, Siffert S, Zhilinskaya EA, Aboukas A (2002) Appl Catal A 234:91

    CAS  Google Scholar 

  55. Alejandre A, Medina F, Salagre P, Correig X, Sueiras JE (1999) Chem Mater 11:939

    CAS  Google Scholar 

  56. Kanan S, Dubey A, Knozinger H (2005) J Catal 231:381

    Google Scholar 

  57. Xu ZP, Zeng HC (2000) J Phys Chem B 104:10206

    CAS  Google Scholar 

  58. Ma W, Zhao N, Yang G, Tian L, Wang R (2011) Desalination 268:20

    CAS  Google Scholar 

  59. Cesteros Y, Salagre P, Medina F, Sueiras J, Tichit D, Coq B (2001) Appl Catal B 32:25

    CAS  Google Scholar 

  60. Titulaer MK (1994) Clay Clay Miner 42:249

    CAS  Google Scholar 

  61. Aramenda M (2002) J Solid State Chem 168:156

    Google Scholar 

  62. Othman MR, Rasid NM, Fernando WJN (2006) Chem Eng Sci 61:1555

    CAS  Google Scholar 

Download references

Acknowledgements

The financial support of the University Grants Commission, Govt. of India through the Dr. D. S. Kothari Post-Doctoral Fellowship (Grant No. D1807) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai, Maharashtra, 400019, India

    Dnyaneshwar D. Subhedar, Prashant A. Yadav, Sonal R. Pawar & Bhalchandra M. Bhanage

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  1. Dnyaneshwar D. Subhedar
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  2. Prashant A. Yadav
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  3. Sonal R. Pawar
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  4. Bhalchandra M. Bhanage
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Subhedar, D.D., Yadav, P.A., Pawar, S.R. et al. Environmentally Benign Synthesis of 4-Thiazolidinone Derivatives Using a Co/Al Hydrotalcite as Heterogeneous Catalyst. Catal Lett 151, 1776–1787 (2021). https://doi.org/10.1007/s10562-020-03436-0

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