Advertisement

Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 1991–1997 | Cite as

Activated Fuller’s earth: an efficient, inexpensive, environmentally benign, and reusable catalyst for rapid solvent-free synthesis of 1-(amido/amino)alkyl-2-naphthols

  • Deelip S. Rekunge
  • Hersh S. Bendale
  • Ganesh U. Chaturbhuj
Original Paper

Abstract

An efficient and entirely green protocol for preparation of 1-(amido/amino)alkyl-2-naphthols via one-pot multi-component reaction of an aldehyde, 2-naphthol or phenol and amides or amines using activated Fuller’s earth as a heterogeneous catalyst under the solvent-free condition is described. This catalyst provides several advantages such as low-cost, stability, reusability, and excellent yields. High catalytic activity and ease of recovery are additional eco-friendly attributes of this catalytic system.

Graphical abstract

Keywords

Activated Fuller’s earth 1-(Amido/amino)alkyl-2-naphthols Amides Solvent free Recyclable catalyst 

Notes

Acknowledgements

The authors are grateful to University Grants Commission, India for their financial supports.

References

  1. 1.
    Thomas JM, Thomas WJ (1996) Principles and practice of heterogeneous catalysis. Wiley-VCH, WeinheimGoogle Scholar
  2. 2.
    Smith GV, Notheisz F (2000) Heterogeneous catalysis in organic chemistry. ElsevierGoogle Scholar
  3. 3.
    Strecker A (1850) Justus Liebigs Ann Chem 75:27CrossRefGoogle Scholar
  4. 4.
    Terrett NK, Gardner M, Gordon DW, Kobylecki RJ, Steele J (1995) Tetrahedron 51:8135CrossRefGoogle Scholar
  5. 5.
    Thompson LA, Ellman JA (1996) Chem Rev 96:555CrossRefPubMedGoogle Scholar
  6. 6.
    Dömling A, Ugi I (2000) Angew Chem Int Ed 39:3168CrossRefGoogle Scholar
  7. 7.
    Ahmed N, van Lier JE (2007) Tetrahedron Lett 48:5407CrossRefGoogle Scholar
  8. 8.
    Dömling A (2006) Chem Rev 106:17CrossRefPubMedGoogle Scholar
  9. 9.
    Cardellicchio C, Capozzi MA, Naso F (2010) Tetrahedron Asymmetry 21:507CrossRefGoogle Scholar
  10. 10.
    Betti M (1941) In: Gilman H (ed) Organic synthesis collective, vol 1. Wiley, New York, p 381Google Scholar
  11. 11.
    Knapp S (1995) Chem Rev 95:1859CrossRefGoogle Scholar
  12. 12.
    Seebach D, Matthews JL (1997) Chem Commun 21:2015CrossRefGoogle Scholar
  13. 13.
    Juaristi E (1997) Enantioselective synthesis of β-amino acids. Wiley, New YorkGoogle Scholar
  14. 14.
    Shen AY, Tsai CT, Chen CL (1999) Eur J Med Chem 34:877CrossRefGoogle Scholar
  15. 15.
    Dingermann T, Steinhilber D, Folkes G (2004) Molecular biology in medicinal chemistry. Wiley-VCHGoogle Scholar
  16. 16.
    Remillard S, Rebhun LI, Howie GA, Kupchan SM (1975) Science 189:1002CrossRefPubMedGoogle Scholar
  17. 17.
    Lesher GY, Surrey AR (1955) J Am Chem Soc 77:636CrossRefGoogle Scholar
  18. 18.
    Mosher HS, Frankel MB, Gregory M (1953) J Am Chem Soc 75:5326CrossRefGoogle Scholar
  19. 19.
    Peglion JL, Vian J, Goument B, Despaux N, Audinot V, Millan MJ (1997) Bioorg Med Chem Lett 7:881CrossRefGoogle Scholar
  20. 20.
    Ren H, Grady S, Gamenara D, Heinzen H, Moyna P, Croft SL, Moyna G (2001) Bioorg Med Chem Lett 11:1851CrossRefPubMedGoogle Scholar
  21. 21.
    Clark RD, Caroon JM, Kluge AF, Repke DB, Roszkowski AP, Strosberg AM, Okada MD (1983) J Med Chem 26:657CrossRefPubMedGoogle Scholar
  22. 22.
    Matsuoka H, Ohi N, Mihara M, Suzuki H, Miyamoto K, Maruyama N, Yano K (1997) J Med Chem 40:105CrossRefPubMedGoogle Scholar
  23. 23.
    Hulst R, Heres H, Peper NC, Kellogg RM (1996) Tetrahedron Asymmetry 7:1373CrossRefGoogle Scholar
  24. 24.
    Li X, Yeung CH, Chan AS, Yang TK (1999) Tetrahedron Asymmetry 10:759CrossRefGoogle Scholar
  25. 25.
    Abou-Elmagd WS, Hashem AI (2013) Med Chem Res 22:2005CrossRefGoogle Scholar
  26. 26.
    Khodaei MM, Khosropour AR, Moghanian H (2006) Synlett 2006:916CrossRefGoogle Scholar
  27. 27.
    Shaterian HR, Yarahmadi H, Ghashang M (2008) Bioorg Med Chem Lett 18:788CrossRefPubMedGoogle Scholar
  28. 28.
    Nandi GC, Samai S, Kumar R, Singh MS (2009) Tetrahedron Lett 50:7220CrossRefGoogle Scholar
  29. 29.
    Hajipour AR, Ghayeb Y, Sheikhan N, Ruoho AE (2009) Tetrahedron Lett 50:5649CrossRefGoogle Scholar
  30. 30.
    Safari J, Zarnegar Z (2013) J Mol Catal A: Chem 379:269CrossRefGoogle Scholar
  31. 31.
    Kumar A, Gupta MK, Kumar M (2012) RSC Adv 2:7371CrossRefGoogle Scholar
  32. 32.
    Davoodnia A, Mahjoobin R, Tavakoli-Hoseini N (2014) Chin J Catal 35:490CrossRefGoogle Scholar
  33. 33.
    Hajjami M, Ghorbani F, Bakhti F (2014) Appl Catal A: Gen 470:303CrossRefGoogle Scholar
  34. 34.
    Shaterian HR, Yarahmadi H, Ghashang M (2008) Tetrahedron 64:1263CrossRefGoogle Scholar
  35. 35.
    Supal AR, Gokavi GS (2010) J Chem Sci 122:189CrossRefGoogle Scholar
  36. 36.
    Kantevari S, Vuppalapati SV, Nagarapu L (2007) Catal Commun 8:1857CrossRefGoogle Scholar
  37. 37.
    Shaterian HR, Yarahmadi H (2008) Tetrahedron Lett 49:1297CrossRefGoogle Scholar
  38. 38.
    Das B, Laxminarayana K, Ravikanth B, Rao BR (2007) J Mol Catal A: Chem 261:180CrossRefGoogle Scholar
  39. 39.
    Samantaray S, Hota G, Mishra BG (2011) Catal Commun 12:1255CrossRefGoogle Scholar
  40. 40.
    Nagarapu L, Baseeruddin M, Apuri S, Kantevari S (2007) Catal Commun 8:1729CrossRefGoogle Scholar
  41. 41.
    Kundu D, Majee A, Hajra A (2010) Catal Commun 11:1157CrossRefGoogle Scholar
  42. 42.
    Das VK, Borah M, Thakur AJ (2013) J Org Chem 78:3361CrossRefPubMedGoogle Scholar
  43. 43.
    Safari J, Zarnegar Z (2014) J Ind Eng Chem 20:2292CrossRefGoogle Scholar
  44. 44.
    Datta B, Pasha MA (2011) Ultrason Sonochem 18:624CrossRefPubMedGoogle Scholar
  45. 45.
    Rekunge DS, Indalkar KS, Chaturbhuj GU (2016) Tetrahedron Lett 57:5815CrossRefGoogle Scholar
  46. 46.
    Khatri CK, Rekunge DS, Chaturbhuj GU (2016) New J Chem 40:10412CrossRefGoogle Scholar
  47. 47.
    Khatri CK, Satalkar VB, Chaturbhuj GU (2017) Tetrahedron Lett 58:694CrossRefGoogle Scholar
  48. 48.
    Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:1240CrossRefGoogle Scholar
  49. 49.
    Indalkar KS, Khatri CK, Chaturbhuj GU (2017) J Chem Sci 129:141CrossRefGoogle Scholar
  50. 50.
    Indalkar KS, Khatri CK, Chaturbhuj GU (2017) J Chem Sci 129:415CrossRefGoogle Scholar
  51. 51.
    Khatri CK, Patil MS, Chaturbhuj GU (2017) J Iran Chem Soc 14:1683CrossRefGoogle Scholar
  52. 52.
    Khatri CK, Mali AS, Chaturbhuj GU (2017) Monatsh Chem 148:1463CrossRefGoogle Scholar
  53. 53.
    Indalkar KS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:2144CrossRefGoogle Scholar
  54. 54.
    Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Monatsh Chem 148:2091CrossRefGoogle Scholar
  55. 55.
    Patil MS, Palav AV, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:2859CrossRefGoogle Scholar
  56. 56.
    Patil MS, Mudaliar C, Chaturbhuj GU (2017) Tetrahedron Lett 58:3250Google Scholar
  57. 57.
    Khatri CK, Chaturbhuj GU (2017) J Iran Chem Soc 14:2513CrossRefGoogle Scholar
  58. 58.
    Indalkar KS, Patil MS, Chaturbhuj GU (2017) Tetrahedron Lett 58:4496CrossRefGoogle Scholar
  59. 59.
    Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:4304CrossRefGoogle Scholar
  60. 60.
    Jejurkar VP, Khatri CK, Chaturbhuj GU, Saha S (2017) Chem Select 2:11693Google Scholar
  61. 61.
    Patil MS, Khatri CK, Chaturbhuj GU (2018) Monatsh Chem.  https://doi.org/10.1007/s00706-018-2169-z CrossRefGoogle Scholar
  62. 62.
    Mali AS, Potnis CS, Chaturbhuj GU (2018) J Iran Chem Soc 15:1399CrossRefGoogle Scholar
  63. 63.
    Bamoniri A, Mirjalili BF, Nazemian S (2014) J Iran Chem Soc 11:653CrossRefGoogle Scholar
  64. 64.
    Hajjami M, Bakhti F, Ghiasbeygi E (2015) Croat Chem Acta 88:197CrossRefGoogle Scholar
  65. 65.
    Kiasat AR, Hemat-Alian L, Saghanezhad SJ (2016) Res Chem Intermed 42:915CrossRefGoogle Scholar
  66. 66.
    Nasresfahani Z, Kassaee MZ, Eidi E (2016) New J Chem 40:4720CrossRefGoogle Scholar
  67. 67.
    Zare A (2012) Org Prep Proced Int 44:82CrossRefGoogle Scholar
  68. 68.
    Zare A, Hasaninejad A, Rostami E, Moosavi-Zare AR, Pishahang N, Roshankar M, Khedri M (2010) J Chem 7:1162Google Scholar
  69. 69.
    Zali A, Shokrolahi A (2012) Chin Chem Lett 23:269CrossRefGoogle Scholar
  70. 70.
    Moeinpour F, Sardashti-Birjandi A, Dorostkar-Ahmadi N, Khojastehnezhad A, Mohseni-Shahri FS (2012) Synth React Inorg, Met-Org, Nano-Met Chem 42:278CrossRefGoogle Scholar
  71. 71.
    Ghodrati K, Farrokhi A, Karami C, Hamidi Z (2015) Synth React Inorg, Met-Org, Nano-Met Chem 45:15CrossRefGoogle Scholar
  72. 72.
    Gupta A, Kour D, Gupta VK, Kapoor KK (2016) Tetrahedron Lett 57:4869CrossRefGoogle Scholar
  73. 73.
    Ghomi JS, Zahedi S (2013) Monatsh Chem 144:687CrossRefGoogle Scholar
  74. 74.
    Shaterian HR, Hosseinian A, Ghashang M (2008) Synth Commun 38:3375CrossRefGoogle Scholar
  75. 75.
    Srihari G, Nagaraju M, Murthy MM (2007) Helv Chim Acta 90:1497CrossRefGoogle Scholar
  76. 76.
    Wang M, Liang Y, Zhang T, Gao J (2011) Chin J Chem 29:1656CrossRefGoogle Scholar
  77. 77.
    Nasr-Esfahani M, Montazerozohori M, Taei M (2016) C R Chim 19:986CrossRefGoogle Scholar
  78. 78.
    Hakimi F (2016) J Chem Res 40:489CrossRefGoogle Scholar
  79. 79.
    Taghrir H, Ghashang M, Biregan MN (2016) Chin Chem Lett 27:119CrossRefGoogle Scholar
  80. 80.
    Tayebee R, Amini MM, Akbari M, Aliakbari A (2015) Dalton Trans 44:9596CrossRefPubMedGoogle Scholar
  81. 81.
    Wang C, Wan Y, Wang HY, Zhao LL, Shi JJ, Zhang XX, Wu H (2013) J Heterocycl Chem 50:496CrossRefGoogle Scholar
  82. 82.
    Maleki B, Taimazi F (2014) Org Prep Proced Int 46:252CrossRefGoogle Scholar
  83. 83.
    Pourmousavi SA, Moghimi P, Ghorbani F, Zamani M (2017) J Mol Struct 1144:87CrossRefGoogle Scholar
  84. 84.
    Azizi N, Edrisi M (2017) Res Chem Intermed 43:379CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Deelip S. Rekunge
    • 1
  • Hersh S. Bendale
    • 1
  • Ganesh U. Chaturbhuj
    • 1
  1. 1.Department of Pharmaceutical Sciences and TechnologyInstitute of Chemical TechnologyMumbaiIndia

Personalised recommendations