Skip to main content
Log in

Eco-friendly synthesis of amidochloroalkylnaphthols and its related oxazepinones with biological evaluation

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

Abstract

A general mild and efficient protocol for the synthesis of amidochloroalkylnaphthol libraries was achieved utilizing SiO2–ZnCl2 (silzic) as a reusable heterogeneous catalyst via Ritter-type reaction, through one-pot, three-component condensation of various aldehydes, chloroacetonitrile, and β-naphthol under solvent-free reaction conditions. The amidochloroalkylnaphthols were cyclized to its related oxazepinones, and their anticancer and antioxidant activities were studied.

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
Fig. 2

Similar content being viewed by others

References

  1. Damodiran M, Selvam NP, Perumal PT (2009) Tetrahedron Lett 50:5474

    Article  CAS  Google Scholar 

  2. Abou-Elmagd WSI, Hashem AI (2013) Med Chem Res 22:2005

    Article  CAS  Google Scholar 

  3. Dabiri M, Delbari AS, Bazgir A (2007) Synlett 821–823

  4. Ghomi JS, Zahedi S (2013) Monatsh Chem 144:687

    Article  CAS  Google Scholar 

  5. Dingermann T, Steinhilber D, Folkers G (2004) Molecular biology in medicinal chemistry. Wiley-VCH, Weinheim

    Google Scholar 

  6. Shen AY, Tsai CT, Chen CL (1999) Eur J Med Chem 34:877

    Article  CAS  Google Scholar 

  7. Shen AY, Chen CL, Lin CI (1992) Chin J Physiol 35:45

    CAS  Google Scholar 

  8. Szatmari I, Fülop F (2004) Curr Org Synth 1:155

    Article  CAS  Google Scholar 

  9. Schenker K (1971) Benzoxazepinones. Swiss Patent 505 850, Apr 15, 1971

  10. Schenker K (1971) Chem Abstr 75:98600

    Google Scholar 

  11. Hirohashi T, Izumi T, Yamamoto H (1970) 7-Chloro-5-phenyl-2,3-dihydro-1,4-benzoxazepine and its 4,5-dihydro derivative with effects on the central nervous system. Ger Offen 2 014 223, Oct 1, 1970

  12. Hirohashi T, Izumi T, Yamamoto H (1970) Chem Abstr 73:120697

    Google Scholar 

  13. Standridge RT (1978) Substituted 5-phenyl-2,3,4,5-tetrahydro-1,4-benzoxazepines. US Patent 4125538, Nov 14, 1978

  14. Standridge RT (1979) Chem Abstr 90:72246

    Google Scholar 

  15. Liao Y, Venhuis BJ, Rodenhuis N, Timmerman W, Wikström H, Meier E, Bartoszyk GD, Böttcher H, Seyfried CA, Sundell S (1999) J Med Chem 42:2235

    Article  CAS  Google Scholar 

  16. Nagarajan K, Venkateswarlu A, Kulkarni CL, Nagana GA, Shah RK (1974) Indian J Chem 12:236

    CAS  Google Scholar 

  17. Nagarajan K, David J, Kulkarn YS, Hendi SB, Shenoy SJ, Upadhyaya P (1986) Eur J Med Chem 21:21

    CAS  Google Scholar 

  18. Agirbas H, Sagdinc S, Kandemirli F, Kemal B (2008) J Mol Struct 892:132

    Article  CAS  Google Scholar 

  19. Sanchez-Viesca F, Gomez MR (1982) Rev Latinoam Quim 13:67

    CAS  Google Scholar 

  20. Katsuhide K, Noriko M, Ryoko O, Makoto K, Mika N, Toshio T, Tomochika O, Teruyoshi I (2001) Bioorg Med Chem Lett 11:595

    Article  Google Scholar 

  21. Schenker K, Druey J (1963) Helv Chim Acta 46:1696

    Article  CAS  Google Scholar 

  22. Derieg ME, Sternbach LH (1966) J Heterocycl Chem 3:237

    Article  CAS  Google Scholar 

  23. Walker GN, Smith RT (1971) J Org Chem 36:305

    Article  Google Scholar 

  24. Katritzky AR, Xu Y-J, He H-Y (2002) J Chem Soc Perkin Trans 1:592

    Article  Google Scholar 

  25. Kost AN (1971) Khim Geterosikl Soedin 7:1288

    CAS  Google Scholar 

  26. Bilgiç S, Bilgiç O, Bilgiç MÖ, Gündüz M, Karakoç N (2009) Arkivoc 13:185

    Google Scholar 

  27. Misiti D, Rimatory V (1973) Ann Ist Super Sanita 9:150

    CAS  Google Scholar 

  28. Kaye PT, Whittal RDS (1991) Afr J Chem 44:30

    CAS  Google Scholar 

  29. Katritzky AR, Xu Y-J, He H-Y, Mehta S (2001) J Org Chem 66:5590

    Article  CAS  Google Scholar 

  30. Kiran B, Archana K, Ashok K (2004) Eur J Med Chem 39:369

    Article  Google Scholar 

  31. Nandi GC, Samai S, Kumar R, Singh MS (2009) Tetrahedron Lett 50:7220

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  33. Lei M, Ma L, Hu L (2009) Tetrahedron Lett 50:6393

    Article  CAS  Google Scholar 

  34. Kumar A, Rao MS, Ahmad I, Khungar B (2009) Can J Chem 87:714

    Article  CAS  Google Scholar 

  35. Gawand P, Deokar H, Langi B, Yadav A, Chaskar A (2009) Synth Commun 39:4171

    Article  CAS  Google Scholar 

  36. Ghorbani-Vaghei R, Malaekehpour SM (2010) Cent Eur J Chem 8:1086

    CAS  Google Scholar 

  37. Lue J, Zhang Q (2011) Monatsh Chem 142:923

    Article  Google Scholar 

  38. Kotadia DA, Soni SS (2011) J Mol Cat A: Chem 44:353

    Google Scholar 

  39. Shaterian HR, Ghashang M, Asadi N, Riki NT (2012) J Iran Chem Soc 9:1

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  41. Selvam NP, Perumal PT (2006) Tetrahedron Lett 47:7481

    Article  CAS  Google Scholar 

  42. Shaterian HR, Yarahmadi H, Ghashang M (2008) Tetrahedron 64:1263

    Article  CAS  Google Scholar 

  43. Shaterian HR, Yarahmadi H (2008) Tetrahedron Lett 49:1297

    Article  CAS  Google Scholar 

  44. Shaterian HR, Yarahmadi H (2008) Arkivoc 2:105

    Google Scholar 

  45. Heravi MM, Tavakoli-Hoseini N, Bamoharram FF (2011) Bulg Chem Commun 43:423

    CAS  Google Scholar 

  46. Khazaei A, Zolfigol MA, Moosavi-Zare AR, Zare A, Parhami A, Khalafi-Nezhad AK (2010) Appl Cat A: Gen 386:179

    Article  CAS  Google Scholar 

  47. Das B, Laxminarayana K, Thirupathi PR (2007) Synlett 3103

  48. Silvam NP, Perumal PT (2008) Tetrahedron 64:2972

    Article  Google Scholar 

  49. Tamaddon F, Bistgani JM (2011) Synlett 2947

  50. Soliman HA, Mubarak AY, El-Mekabati A, Elmorsy SS (2014) Chem Sci Trans 3:618

    Google Scholar 

  51. Soliman HA, Salama TA (2014) Org Chem: An Indian J 10:63

    CAS  Google Scholar 

  52. Soliman HA, Salama TA (2013) Chin Chem Lett 24:404

    Article  CAS  Google Scholar 

  53. Salama TA, Ismail MA, Khalil AM, Elmorsy SS (2012) Arkivoc 9:242

    Google Scholar 

  54. Salama TA, Elmorsy SS (2011) Chin Chem Lett 22:1171

    CAS  Google Scholar 

  55. Elmorsy SS, Badawy DS, Khatab TK (2006) Phosphorus Sulfur Silicon Relat Elem 181:2005

    Article  CAS  Google Scholar 

  56. Salama TA (2013) Synlett 24:713

    Article  CAS  Google Scholar 

  57. Upadhya DJ, Samant SD (2008) Appl Catal A: Gen 340:42

    Article  Google Scholar 

  58. Hamdy NA, Anwar MM, Abu-Zied KM, Awad HM (2013) Acta Pol Pharm Drug Res 70:987

    CAS  Google Scholar 

  59. Michael HN, Awad HM, El-Sayed NH, Pare PW (2010) Pharm Biol 48:534

    Article  CAS  Google Scholar 

  60. Soliman HA, Yousif MNM, Said MM, Hassan NA, Ali MM, Awad HM, Abdel-Megeid FME (2014) Pharma Chem 6:394

    Google Scholar 

  61. Awad HM, Abd-Alla HI, Mahmoud KH, El-Toumy SA (2014) Med Chem Res 23:3298

    Article  CAS  Google Scholar 

  62. Almajhdi FN, Fouad H, Khalil KA, Awad HM, Mohamed SHS (2014) J Mater Sci Mater Med 25:1

    Article  Google Scholar 

Download references

Acknowledgments

Financial support by National Research Center (Cairo, Egypt) is gratefully appreciated.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hanan A. Soliman.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2356 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Soliman, H.A., Mubarak, A.Y., El-Mekabaty, A. et al. Eco-friendly synthesis of amidochloroalkylnaphthols and its related oxazepinones with biological evaluation. Monatsh Chem 147, 809–816 (2016). https://doi.org/10.1007/s00706-015-1536-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1536-2

Keywords

Navigation