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Sulfonic acid@pericarp-pomegranate: A natural supported catalyst for synthesis of bis(indolyl)alkanes

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Abstract

A heterogeneous solid acid catalyst, sulfonic acid supported on pericarp-pomegranate (sulfonic acid@PP) is prepared with green an eco-friendly approach. The prepared sulfonic acid@PP catalyst was extensively characterized by IR, FE-SEM, EDX and TGA techniques. The efficiency of the catalyst  has been investigated for the synthesis of bis(indolyl)alkanes by electrophilic substitution reaction of indoles with carbonyl compounds in ethanol at 80 oC. Easy recovery by simple filtration and at least three times reusability without significant loss in the yield of the desired product are conspicuous features of the reported catalyst. In addition, the notable features of this protocol are high conversions, shorter reaction times, cleaner reaction profile, simple experimental and work-up procedure.

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References

  1. Bell R, Carmeli S, Sar N (1994) J Nat Prod 57:1587–1590

    CAS  PubMed  Google Scholar 

  2. Benabadji SH, Wen R, Zheng J, Dong X, Yuan S (2004) Acta Pharmacol Sin 25:666–671

    CAS  PubMed  Google Scholar 

  3. Fahy E, Potts BCM, Faulkner DJ, Smith K (1991) J Nat Prod 54:564–569

    CAS  Google Scholar 

  4. Irie T, Kubushirs K, Suzuki K, Tsukazaki K, Umezawa K, Nozawa S (1999) Anticancer Res 31:3061–3066

    Google Scholar 

  5. Kamal A, Khan MNA, Reddy KS, Srikanth YVV, Ahmed SK, Kumar KP, Murthy US (2009) J Enzym Inhib Med Chem 24:559–565

    CAS  Google Scholar 

  6. Kobayashi M, Aoki S, Gato K, Matsunami K, Kurosu M, Kitagawa I (1984) Chem Pharm Bull 42:2449–2451

    Google Scholar 

  7. Kuethe JT (2006) Chimia 60:543–553

    CAS  Google Scholar 

  8. Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z (2010) Chem Rev 110:2250–2293

    CAS  PubMed  Google Scholar 

  9. Sivaprasad G, Perumal PT, Prabavathy VR, Mathivanan N (2006) Bioorg Med Chem Lett 16:6302–6305

    CAS  PubMed  Google Scholar 

  10. Sujatha K, Perumal PT, Muralidharan D, Rajendran M (2009) Indian J Chem 48B:267–272

    CAS  Google Scholar 

  11. Zeligs MA (1998) J Med Food 1:67–70

    CAS  Google Scholar 

  12. Wang Y, Sang R, Zheng Y, Guo L, Guan M, Wu Y (2017) Catal Commun 89:138–142

    CAS  Google Scholar 

  13. Nagarajan R, Perumal PT (2002) Tetrahedron 58:1229–1232

    CAS  Google Scholar 

  14. Bandgar BP, Shaikh KA (2003) Tetrahedron Lett 44:1959–1961

    CAS  Google Scholar 

  15. Yadav JS, Reddy BVS, Murthy VSR, Kumar GM, Kumar M (2001) Synthesis 5:783–787

    Google Scholar 

  16. Ghorbani-Vaghei R, Veisi H, Keypour H, Dehghani-Firouzabadi AA (2010) Mol Divers 14:87–97

    CAS  PubMed  Google Scholar 

  17. Nagarajan R, Perumal PT (2004) Chem Lett 3:288–289

    Google Scholar 

  18. Singh PR, Singh DU, Samant SD (2005) Synth Commun 35:2133–2138

    CAS  Google Scholar 

  19. Siadatifard SH, Abdoli-Senejani M, Bodaghifard MA (2016) Cogent Chem 2:1188435–1188441

    Google Scholar 

  20. Sharma GVM, Reddy JJ, Lakshmi PS, Krishna PR (2004) Tetrahedron Lett 45:7729–7732

    CAS  Google Scholar 

  21. Merinosa JPG, Ruiza HL, Lopez Y, Limaa SR (2015) Lett Org Chem 12:332–336

    Google Scholar 

  22. Magesh CJ, Nagarajan R, Karthik M, Perumal PT (2004) Appl Catal A Gen 266:1–10

    CAS  Google Scholar 

  23. Karthik M, Tripathi AK, Gupta NM, Palanichamy M, Murugesan V (2004) Catal Commun 5:371–375

    CAS  Google Scholar 

  24. Hosseini-Sarvari M (2008) Synth Commun 38:832–840

    CAS  Google Scholar 

  25. Harichandran G, Amalraj SD, Shanmugam P (2016) J Saudi Chem Soc 22:208–217

    Google Scholar 

  26. Babu G, Sridhar N, Perumal PT (2000) Synth Commun 30:1609–1614

    CAS  Google Scholar 

  27. Satam JR, Parghi KD, Jayaram RV (2008) Catal Commun 9:1071–1078

    CAS  Google Scholar 

  28. Veisi H, Sedrpoushan A, Zolfigol MA, Mohanazadeh F (2011) J Heterocyclic Chem 48:1448–1454

    CAS  Google Scholar 

  29. Reddy BM, Sreekanth PM, Lakshmanan P (2005) J Mol Catal A 237:93–100

    CAS  Google Scholar 

  30. Meshram GA, Patil VD (2010) Synth Commun 40:29–38

    CAS  Google Scholar 

  31. Yadav JS, Reddy BVS, Sunitha S (2003) Adv Synth Catal 345:349–352

    CAS  Google Scholar 

  32. Mi X, Luo S, He J (2004) C Jin-Pei. Tetrahedron Lett 45:4567–4571

    CAS  Google Scholar 

  33. Mo LP, Ma ZC, Zhang ZH (2005) Synth Commun 35:1997–2004

    CAS  Google Scholar 

  34. Nguyen HTD, Nguyen TT, Nguyen PTK, Tran PH (2020) Arab J Chem 13:1377–1385

    CAS  Google Scholar 

  35. Pokhre R, Ghosh D, Jha S, Bhattacharyya NK, Jha S (2014) Int J Innov Res Sci Eng Tech 3:15666–15671

    Google Scholar 

  36. Deb ML, Deka B, Saikia PJ, Baruah PK (2017) Tetrahedron Lett 58:1999–2003

    CAS  Google Scholar 

  37. Sobhani S, Jahanshahi R (2013) New J Chem 37:1009–1015

    CAS  Google Scholar 

  38. Reddy MK, Gupta SK, Jacob MR, Khan SI, Ferreira D (2007) Planta Med 73:461–467

    CAS  PubMed  Google Scholar 

  39. Kotwal GJ (2008) Vaccine 26:3055–3058

    CAS  PubMed  Google Scholar 

  40. Bell C, Hawthorne S (2008) J Pharm Pharmacol 60:139–144

    CAS  PubMed  Google Scholar 

  41. Seeram NP, Adams LS, Henning SM, Niu Y, Zhang Y, Nair MG, Heber D (2005) J Nutr Biochem 16:360–367

    CAS  PubMed  Google Scholar 

  42. Negi PS, Jayaprakash GK, Jena BS (2003) Food Chem 80:393–397

    CAS  Google Scholar 

  43. Seeram N, Lee R, Hardy M, Heber D (2005) Sep Purif Technol 41:49–55

    CAS  Google Scholar 

  44. Amin NK (2009) J Hazard Mater 165:52–62

    CAS  PubMed  Google Scholar 

  45. Bhatnagar A, Minocha AK (2009) J Hazard Mater 168:1111–1116

    CAS  PubMed  Google Scholar 

  46. El-Ashtoukhya ESZ, Amin NK, Abdelwahab O (2008) Desalination 223:162–173

    Google Scholar 

  47. El Nemr A (2007) Chem Ecol 23:409–425

    Google Scholar 

  48. El Nemr A (2009) J Hazard Mater 161:132–141

    CAS  Google Scholar 

  49. Bhatnagar A, Minocha AK (2010) Colloids Surf B Biointerfaces 76:544–548

    CAS  PubMed  Google Scholar 

  50. Rohani Moghadam M, Nasirizadeh N, Dashti Z, Babanezhad E (2013) Int J Ind Chem 4:19–24

    Google Scholar 

  51. Sadeghi B, Bouslik M, Shishehbore MR (2015) J Iran Chem Soc 12:1801–1808

    CAS  Google Scholar 

  52. Tayebee R, Amini MM, Nehzat F, Sadeghi O, Armaghan M (2013) J Mol Catal A 366:140–148

    CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, Rajaram College, Kolhapur, Maharashtra, 416004, India

    Monika Patil, Shrikrishna Karhale, Chandrakant Bhenki & Vasant Helavi

  2. Department of Chemistry, P. D. V. P. College, Tasgaon, Maharashtra, 416312, India

    Arjun Kumbhar

  3. Department of Chemistry, Sanjay Ghodawat University, Kolhapur, Maharashtra, 416118, India

    Monika Patil

  4. Karmaveer Bhaurao Patil Mahavidyalaya, Mahavidyalaya, Pandharpur (Autonomous), Dist, Solapur, Maharashtra, 413304, India

    Shrikrishna Karhale

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  1. Monika Patil
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  2. Shrikrishna Karhale
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  4. Arjun Kumbhar
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Correspondence to Monika Patil.

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Patil, M., Karhale, S., Bhenki, C. et al. Sulfonic acid@pericarp-pomegranate: A natural supported catalyst for synthesis of bis(indolyl)alkanes. Reac Kinet Mech Cat 130, 993–1007 (2020). https://doi.org/10.1007/s11144-020-01828-2

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