Skip to main content
Log in

Three-component, solvent-free synthesis of Betti base catalyzed by sulfated polyborate

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

In this work, efficient, mild, and eco-friendly procedure of 1-aminoalkyl-2-phenol/Betti base from one-pot three-component condensations of aldehyde, phenol, and morpholine in the presence of sulfated polyborate catalyst, under a solvent-free condition at 100 °C, is described. The key advantages of the present method are short reaction time, high yields, aqueous work-up procedure, low cost, stable, reusable catalyst, and solvent-free reaction conditions.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  1. Betti M (1929) Org Synth 9:60

    Article  CAS  Google Scholar 

  2. Betti M (1900) Gazz Chim Ital 30:310

    CAS  Google Scholar 

  3. Betti M (1901) Gazz Chim Ital 31:377

    CAS  Google Scholar 

  4. Betti M (1901) Gazz Chim Ital 31:170

    Google Scholar 

  5. Betti M (1901) Gazz Chim Ital 31:191

    CAS  Google Scholar 

  6. Betti M (1941) In: Gilman H (ed) Organic syntheses collective, vol I. John Wiley & Sons, New York, p 381

    Google Scholar 

  7. Betti M (1906) Gazz Chim Ital 36:392

    Google Scholar 

  8. Betti M (1906) Gazz Chim Ital 36:666

    Google Scholar 

  9. Gerlach M, Maul C (2007) Preparation of α-aminobenzylnaphthols and analogs as analgesics. U.S. Patent 7202242 B2, Apr 10, 2007; (2001) Chem Abstr 135:76698

  10. Lu J, Xu X, Wang C, He J, Hu Y, Hu H (2002) Tetrahedron Lett 43:8367

    Article  CAS  Google Scholar 

  11. Feng J, Bohle DS, Li CJ (2007) Tetrahedron Asymmetry 18:1043

    Article  CAS  Google Scholar 

  12. Kidwai M, Chauhan R (2013) Asian J Org Chem 2:395

    Article  CAS  Google Scholar 

  13. Gomez PG, Pabon HP, Carvajal MA, Rincon JM (1985) Rev Colomb Cienc Quim Farm 8:15

    Google Scholar 

  14. Waisser K, Gregor K, Kubicova L, Klimesova V, Kunes J, Machacek M, Kaustova (2000) Eur J Med Chem 35:733

    Article  CAS  PubMed  Google Scholar 

  15. Bouaziz Z, Riondel J, Mey A, Berlion M, Villard J, Filliond H (1991) Eur J Med Chem 26:469

    Article  CAS  Google Scholar 

  16. Arthington SB, Motley AM, Warnock DW, Morrison CJ (2000) J Clin Microbiol 38:2254

    Google Scholar 

  17. Chylinska JB, Urbanski T, Mordarski M (1963) J Med Chem 6:484

    Article  CAS  PubMed  Google Scholar 

  18. Benameur L, Bouaziz Z, Nebois P, Bartoli MH, Boitard M, Fillion H (1996) Chem Pharm Bull 44:605

    Article  CAS  PubMed  Google Scholar 

  19. Mathew BP, Kumar A, Sharma S, Shukla PK, Nath M (2010) Eur J Med Chem 45:1502

    Article  CAS  PubMed  Google Scholar 

  20. Petrlíková E, Waisser K, Divišová H, Husáková P, Vrabcová P, Kuneš J, Kolář K, Stolaříková J (2010) Bioorg Med Chem 18:8178

    Article  CAS  PubMed  Google Scholar 

  21. Mojtahedi M, Shari A, Mohsenzadeh F, Saidi MR (2000) Synth Commun 30:69

    Article  CAS  Google Scholar 

  22. Littman JB, Brode WR (1930) J Am Chem Soc 52:1655

    Article  CAS  Google Scholar 

  23. Brode WR, Littman JB (1931) J Am Chem Soc 53:1531

    Article  CAS  Google Scholar 

  24. Grumbach HJ, Arend M, Risch N (1996) Synthesis 1996:883

  25. Katritzky AR, Abdel-Fattah Ashraf AA, Tymoshenko DO, Belyakov SA, Ghiviriga I, Steel PJ (1999) J Org Chem 64:6071

    Article  CAS  Google Scholar 

  26. Safari J, Zarnegar Z (2013) J Mol Catal A Chem 379:269

    Article  CAS  Google Scholar 

  27. Hajjami M, Ghorbani F, Bakhti F (2014) Appl Catal A 470:303

    Article  CAS  Google Scholar 

  28. Hajipour AR, Ghayeb Y, Sheikhan N, Ruoho AE (2009) Tetrahedron Lett 50:5649

    Article  CAS  Google Scholar 

  29. Zali A, Shokrolahi A (2012) Chin Chem Lett 23:269

    Article  CAS  Google Scholar 

  30. Das B, Laxminarayana K, Ravikamth B, Rao BR (2007) J Mol Catal A Chem 261:180

    Article  CAS  Google Scholar 

  31. Hashemi H, Sardarian AR (2013) J Iran Chem Soc 10:745

    Article  CAS  Google Scholar 

  32. Wang M, Liang Y, Zhang TT, Gao JJ (2012) Chin Chem Lett 23:65

    Article  CAS  Google Scholar 

  33. Khatri CK, Satalkar VB, Chaturbhuj GU (2017) Tetrahedron Lett 58:694

    Article  CAS  Google Scholar 

  34. Khatri CK, Mali AS, Chaturbhuj GU (2017) Monatsh Chem 148:1463

    Article  CAS  Google Scholar 

  35. Indalkar KS, Khatri CK, Chaturbhuj GU (2017) J Chem Sci 129:415

    Article  CAS  Google Scholar 

  36. Khatri CK, Rekunge DS, Chaturbhuj GU (2016) New J Chem 40:10412

    Article  CAS  Google Scholar 

  37. Indalkar KS, Khatri CK, Chaturbhuj GU (2017) J Chem Sci 129:141

    Article  CAS  Google Scholar 

  38. Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:1240

    Article  CAS  Google Scholar 

  39. Indalkar KS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:2144

    Article  CAS  Google Scholar 

  40. Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Monatsh Chem 148:2091

    Article  CAS  Google Scholar 

  41. Patil MS, Palav AV, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:2859

    Article  CAS  Google Scholar 

  42. Patil MS, Mudaliar C, Chaturbhuj GU (2017) Tetrahedron Lett 58:3256

    Article  CAS  Google Scholar 

  43. Khatri CK, Chaturbhuj GU (2017) J Iran Chem Soc 14:2513

    Article  CAS  Google Scholar 

  44. Khatri CK, Patil MS, Chaturbhuj GU (2017) J Iran Chem Soc 14:1683

    Article  CAS  Google Scholar 

  45. Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:4304

    Article  CAS  Google Scholar 

  46. Indalkar KS, Patil MS, Chaturbhuj GU (2017) Tetrahedron Lett 58:4496

    Article  CAS  Google Scholar 

  47. Jejurkar VP, Khatri CK, Chaturbhuj GU, Saha S (2017) ChemistrySelect 2:11693

    Article  CAS  Google Scholar 

  48. Liu F, Li G, Jiang J, Zheng F, Wu M (2015) Tetrahedron Lett 56:5054

    Article  CAS  Google Scholar 

  49. Karmakara B, Banerji J (2011) Tetrahedron Lett 52:4957

    Article  CAS  Google Scholar 

  50. Kumar A, Gupta MK, Kumar M (2010) Tetrahedron Lett 51:1582

    Article  CAS  Google Scholar 

  51. Rosholm T, Gois PMP, Franzen R, Candeias NR (2015) ChemistryOpen 4:39

    Article  CAS  PubMed  Google Scholar 

  52. Erb W, Albini M, Rouden J, Blanchet J (2014) J Org Chem 79:10568

    Article  CAS  PubMed  Google Scholar 

  53. Zhen M, Zhang D, Zhang Z, Peng Y (2016) ACS Comb Sci 18:697

    Article  CAS  PubMed  Google Scholar 

  54. Reddy BN, Rani CR, Reddy SM, Pathak M (2016) Res Chem Intermed 42:7533

    Article  CAS  Google Scholar 

  55. Waghmode N, Kalbandhe AH, Thorat PB, Karade NN (2015) Tetrahedron Lett 12:117

    Google Scholar 

Download references

Acknowledgements

The authors are grateful to the Department of Science and Technology, New Delhi, India for their financial supports.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ganesh U. Chaturbhuj.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 167 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patil, M.S., Khatri, C.K. & Chaturbhuj, G.U. Three-component, solvent-free synthesis of Betti base catalyzed by sulfated polyborate. Monatsh Chem 149, 1453–1457 (2018). https://doi.org/10.1007/s00706-018-2169-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2169-z

Keywords

Navigation