Skip to main content
Log in

An expedient “on-water” synthesis of quinoxalines

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

Abstract

An expedient and eco-friendly method for synthesis of quinoxalines and related compounds by the reaction of various 1,2-diketones with 1,2-diamines “on water” has been developed. The method gives very good to excellent yield of the products within 0.5–4 h.

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.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. He W, Meyers MR, Hanney B, Spada AP, Blider G, Galzeinski H, Amin D, Needle S, Page K, Jayyosi Z, Perrone MH (2003) Bioorg Med Chem Lett 13:3097

    Article  CAS  Google Scholar 

  2. Kim YB, Kim YH, Park JY, Kim SK (2004) Bioorg Med Chem Lett 14:541

    Article  CAS  Google Scholar 

  3. Park Y-S, Shin W-S, Kim S-K (2008) J Antimicrob Chemother 61:163

    Article  CAS  Google Scholar 

  4. Cholo MC, Steel HC, Fourie PB, Germishuizen WA, Anderson R (2012) J Antimicrob Chemother 67:290

    Article  CAS  Google Scholar 

  5. Chen B-C, Zhao R, Bednarz MS, Wang B, Sundeen JE, Barrish JC (2004) J Org Chem 69:977

    Article  CAS  Google Scholar 

  6. Chen P, Norris D, Iwanowicz EJ, Spergel SH, Lin J, Gu HH, Shen Z, Wityak J, Lin T-A, Pang S, De Fex HF, Pitt S, Shen DR, Doweyko AM, Bassolino DA, Roberge JY, Poss MA, Chen B-C, Schieven GL, Barrish JC (2002) Bioorg Med Chem Lett 12:1361

    Article  CAS  Google Scholar 

  7. Dailey S, Feast WJ, Peace RJ, Sage IC, Tilla S, Wooda EL (2001) J Mater Chem 11:2238

    Article  CAS  Google Scholar 

  8. Nageswar YVD, Reddy KHV, Ramesh K, Murthy SN (2013) Org Prep Proced Int 45:1

    Article  CAS  Google Scholar 

  9. Dhakshinamoorthy A, Kanagaraj K, Pitchumani K (2011) Tetrahedron Lett 52:69

    Article  CAS  Google Scholar 

  10. Chavan H, Adsul L, Bandgar BP (2011) J Chem Sci 123:477

    Article  CAS  Google Scholar 

  11. Das PJ, Sarkar S (2011) Int J Chem Res 3:56

    Article  Google Scholar 

  12. Gu X, Li X, Chai Y, Yang Q, Li P, Yao Y (2011) Green Chem 13:1640

    Article  Google Scholar 

  13. Sajjadifar S, Zolfigol MA, Mirshokraie SA, Miri S, Louie O, Nezhad ER, Karimian S, Darvishi G, Donyadari E, Farahmand S (2012) Am J Org Chem 2:97

    Article  CAS  Google Scholar 

  14. Beheshtiha YS, Heravi MM, Amrollah M, Saeedi M, Fallah A (2012) Chem Sci Trans 1:134

    Article  Google Scholar 

  15. Khaksar S, Rostamnezhad F (2012) Bull Korean Chem Soc 33:2581

    Article  CAS  Google Scholar 

  16. Soleymni R, Niakan N, Tayeb S, Hakimi S (2012) Orient J Chem 28:687

    Article  Google Scholar 

  17. Ruiz DM, Autino JC, Quaranta N, Vazquez PG, Romanelli GP (2012) Sci World J 1

  18. Sadeghi B, Karimi F (2013) Iran J Catal 3:1

    CAS  Google Scholar 

  19. Hakimia F, Mirjalilib BBF (2013) Curr Chem Lett 2:1

    Article  Google Scholar 

  20. Kadam HK, Khan S, Kunkalkar RA, Tilve SG (2013) Tetrahedron Lett 54:1003

    Article  CAS  Google Scholar 

  21. Duval RA, Lever JR (2010) Green Chem 12:304

    Article  CAS  Google Scholar 

  22. Li C-J, Chen L (2006) Chem Soc Rev 35:68

    Article  Google Scholar 

  23. Hasaninejad A, Zare A, Zolfigol MA, Shekouhy M (2009) Synth Commun 39:569

    Article  CAS  Google Scholar 

  24. Beheshtiha YS, Heravi MM, Saeedi M, Karimi N, Zakeri M, Hossieni TN (2010) Synth Commun 40:1216

    Article  CAS  Google Scholar 

  25. Liu J-Y, Liu J, Wang J-D, Jiao D-Q, Liu H-W (2010) Synth Commun 40:2047

    Article  CAS  Google Scholar 

  26. Khaksar S, Alipour M (2013) Monatsh Chem 144:395

    Article  CAS  Google Scholar 

  27. Xu H, Deng H, Li Z, Xiang H, Zhou X (2013) Eur J Org Chem 7054

  28. Andrade CKZ, Barreto ADFS, Silva WA (2008) Arkivoc 226

  29. Piltan M, Moradi L, Abasi G, Zarei SA (2013) Beilstein J Org Chem 9:510

    Article  CAS  Google Scholar 

  30. He Y, Zhang X, Cui L, Wang J, Fan X (2012) Green Chem 14:3429

    Article  CAS  Google Scholar 

  31. Tada N, Cui L, Okubo H, Miura T, Itoh A (2010) Chem Commun 46:1772

    Article  CAS  Google Scholar 

  32. Kumar A, Kumar M, Gupta MK, Gupta LP (2012) RSC Adv 2:8277

    Article  CAS  Google Scholar 

  33. Liu J, Lei M, Hu L (2012) Green Chem 14:2534

    Article  CAS  Google Scholar 

  34. Xie Z-B, Wang N, Wu M-Y, He T, Le Z-G, Yu X-Q (2012) Beilstein J Org Chem 8:534

    Article  CAS  Google Scholar 

  35. Galletti P, Pori M, Giacomini D (2011) Eur J Org Chem 3896

  36. Mallik AK, Pal R, Guha C, Mallik H (2012) Green Chem Lett Rev 5:321

    Article  CAS  Google Scholar 

  37. Das Gupta A, Samanta S, Mondal R, Mallik AK (2012) Bull Korean Chem Soc 33:4239

    Article  CAS  Google Scholar 

  38. Li C-J, Chan T-H (1997) Organic Reactions in Aqueous Media. John Wiley & Sons, New York, p 1

    Google Scholar 

  39. Niknam K, Saberi D, Mohagheghnejad M (2009) Molecules 14:1915

    Article  CAS  Google Scholar 

  40. Karami B, Khodabakhshi S, Nikrooz M (2011) Polycycl Arom Compd 31:97

    Article  CAS  Google Scholar 

  41. Hou J-T, Liu Y-H, Zhang Z-H (2010) J Heterocycl Chem 47:703

    CAS  Google Scholar 

  42. Sharma RK (2011) Catal Commun 12:327

    Article  CAS  Google Scholar 

  43. Lue H-Y (2010) Austr J Chem 63:1290

    Article  CAS  Google Scholar 

  44. Haftbaradaran F, Draper ND, Leznoff DB, Williams VE (2003) Dalton Trans 2105

  45. Sajjadifar S, Zolfigol MA, Chehardoli G, Miri S, Moosavi P (2013) Int J ChemTech Res 5:422

    CAS  Google Scholar 

  46. Cai J–J (2008) Tetrahedron Lett 49:7386

    Article  CAS  Google Scholar 

  47. Shi D-Q, Dou G-L (2008) Synth Commun 38:3329

    Article  CAS  Google Scholar 

  48. Neumann H, Brennführer A, Beller M (2012) Chem Eur J 14:3645

    Article  Google Scholar 

  49. Akkilagunta VK, Reddy VP, Kakulapati RR (2010) Synlett 17:2571

    Google Scholar 

Download references

Acknowledgments

Financial assistance from the UGC-CAS and DST-PURSE programs, Department of Chemistry is gratefully acknowledged. The authors also acknowledge the DST-FIST program to the Department of Chemistry, Jadavpur University for providing the NMR spectral data. SS and AD are thankful to CSIR, New Delhi for their Research Fellowships.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Asok K. Mallik.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1092 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Samanta, S., Das Gupta, A. & Mallik, A.K. An expedient “on-water” synthesis of quinoxalines. Monatsh Chem 145, 1669–1673 (2014). https://doi.org/10.1007/s00706-014-1242-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1242-5

Keywords

Navigation