Skip to main content
SpringerLink
Log in

Catalyst-free, efficient, and green procedure for the synthesis of 5-heterocyclic substituted 6-aminouracils

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

Abstract

In this paper, the results of our studies on the catalyst-free synthesis of some new 6-aminouracils bearing naphthoquinone, benzo[a]phenazine, benzo[f]pyrido[2,3-b]quinoxaline, and benzo[f]quinoxaline substituents are reported. At first, 6-amino-5-(3,4-dioxo-1-naphthalenyl)uracil derivatives were synthesized from the reaction of various 6-aminouracils with 1,2-naphthoquinone in DMSO at 70 °C in good to excellent yields. Subsequently, the prepared 6-amino-5-(3,4-dioxo-1-naphthalenyl)uracils were subjected to the condensation reaction with various vicinal diamines, in chloroform under reflux conditions to synthesize 6-aminouracils bearing benzo[a]phenazine, benzo[f]pyrido[2,3-b]quinoxaline, and benzo[f]quinoxaline derivatives.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Kundul NG, Dasguptal SK, Chaudhuril LN, Mahantyl JS, Spearsa CP, Shahinianz AH (1993) Eur J Med Chem 28:473

    Article  Google Scholar 

  2. El-Kalyoubi SA, Fayed EA, Abdel-Razek AS (2017) Chem Central J 11:1

    Article  CAS  Google Scholar 

  3. Liu YY, Zeng SY, Leu YL, Tsai TY (2015) J Agric Food Chem 63:7333

    Article  CAS  PubMed  Google Scholar 

  4. Yazdanbakhsh MR, Abbasnia M, Sheykhan M, Ma’mani L (2010) J Mol Struct 977:266

    Article  CAS  Google Scholar 

  5. Mori M, Hatta H, Nishimoto S (2000) J Org Chem 65:4641

    Article  CAS  PubMed  Google Scholar 

  6. Dafali A, Hammouti B, Mokhlisse R, Kertit S (2003) Corros Sci 45:1619

    Article  CAS  Google Scholar 

  7. Yadav DK, Quraishi MA (2012) Ind Eng Chem Res 51:14966

    Article  CAS  Google Scholar 

  8. Bakkialakshmi S, Chandrakala D (2012) J Mol Liq 168:1

    Article  CAS  Google Scholar 

  9. Andree R, Drewes MW, Dollinger MS (2000) Substituted phenyl uracils and their use as herbicides. US Patent 6,107,252, Aug 22, 2000; (1997). Chem Abstr 128:13172

    Google Scholar 

  10. Drewes MW, Andree R, Dollinger M (2001) Substituted phenyl uracils. US Patent 6,245,714, Jun 12, 2001; (1997). Chem Abstr 128:48237

    Google Scholar 

  11. Speer JH, Raymond AL (1953) J Am Chem Soc 75:114

    Article  CAS  Google Scholar 

  12. Sariri R, Khalili G (2002) Russ J Org Chem 38:1053

    Article  CAS  Google Scholar 

  13. Kochergin PM, Aleksandrova EV, Persanova LV (2001) Pharm Chem J 35:388

    Article  CAS  Google Scholar 

  14. Thiede HM, Kehr W (2016) Dermal and/or transdermal pharmaceutical composition containing a terpenoid compound. US Patent 20160317661, Nov 3, 2016; (2015). Chem Abstr 163:109100

    Google Scholar 

  15. Sarg MTM, El-Shaer SS (2014) Open J Med Chem 4:39

    Article  CAS  Google Scholar 

  16. Morel B, Franck P, Bidange J, Sergeyev S, Smith DA, Moseley JD, Maes BU (2017) ChemSusChem 10:624

    Article  CAS  PubMed  Google Scholar 

  17. Freeman NS, Moore CE, Wilhelmsson LM, Tor Y (2016) J Org Chem 81:4530

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Chavan SS, Shelke RU, Degani MS (2013) Monatsh Chem 144:399

    Article  CAS  Google Scholar 

  19. Mohammadi Ziarani G, Hosseini Nasab N, Lashgari N (2016) RSC Adv 6:38827

    Article  CAS  Google Scholar 

  20. Khurana JM, Chaudhary A, Lum A, Nand B (2012) Green Chem 14:2321

    Article  CAS  Google Scholar 

  21. Traube W (1900) Chem Ber 33:3035

    Article  CAS  Google Scholar 

  22. Papech V, Schroeder EF (1951) J Org Chem 16:1879

    Article  Google Scholar 

  23. Nesterov VM, Kucherya LA, Tret’yakova LA, Markitantova LI (1981) Pharm Chem J 15:591

    Article  Google Scholar 

  24. Devi I, Bhuyan PJ (2005) Tetrahedron Lett 46:5727

    Article  CAS  Google Scholar 

  25. Fulle F, Muller CE (2000) Heterocycles 53:347

    Article  CAS  Google Scholar 

  26. Shishoo CJ, Jain KS, Jain SR, Shah SV, Ravikumar T (1996) Indian J Chem 35B:662

    CAS  Google Scholar 

  27. Chavan SS, Degani MS (2012) Green Chem 14:296

    Article  CAS  Google Scholar 

  28. Muller CE (1991) Tetrahedron Lett 32:6531

    Google Scholar 

  29. Priego EM, Camarasa MJ, Pérez-Pérez MJ (2001) Synthesis:478

  30. Seferoğlu Z (2009) Arkivoc vii:42

    Google Scholar 

  31. Wright GE (1980) J Org Chem 45:3128

    Article  CAS  Google Scholar 

  32. Lee IY, Lee JY, Gong Y-D (2005) Synthesis:2713

  33. Shim JL, Niess R, Broom AD (1972) J Org Chem 37:578

    Article  CAS  PubMed  Google Scholar 

  34. Mohammadizadeh MR, Bahramzadeh M, Taghavi SZ (2010) Tetrahedron Lett 51:5807

    Article  CAS  Google Scholar 

  35. Qing D, Chongzhao R, Harvey RG (2005) Org Lett 7:999

    Article  CAS  Google Scholar 

  36. Prachi S, Abhishek B, Justin TKR (2011) J Org Chem 76:6134

    Article  CAS  Google Scholar 

  37. Laursen JB, Nielsen J (2004) Chem Rev 104:1663

    Article  CAS  PubMed  Google Scholar 

  38. Gao X, Lu Y, Xing Y, Ma Y, Lu J, Bao W, Wang Y, Xi T (2012) Microbiol Res 167:616

    Article  CAS  PubMed  Google Scholar 

  39. Zhuo ST, Li CY, Hu MH, Chen SB, Yao PF, Huang SL, Ou TM, Tan JH, An LK, Li D, Gu LQ (2013) Org Biomol Chem 11:3989

    Article  CAS  PubMed  Google Scholar 

  40. Jahani F, Tajbakhsh M, Golchoubian H, Khaksar S (2011) Tetrahedron Lett 52:1260

    Article  CAS  Google Scholar 

  41. Wang SL, Cheng C, Wu FY, Jiang B, Shi F, Tu SJ, Rajale T, Li G (2011) Tetrahedron 67:4485

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. McClure KF, Abramov YA, Laird ER, Barberia JT, Cai W, Carty TJ, Cortina SR, Danley DE, Dipesa AJ, Donahue KM, Dombroski MA (2005) J Med Chem 48:5728

    Article  CAS  PubMed  Google Scholar 

  43. Ostrowska K, Szymoniak K, Szczurek M, Jamrozy K, Rapala-Kozik M (2011) Tetrahedron 67:5219

    Article  CAS  Google Scholar 

  44. Dandia A, Parewa V, Maheshwari S, Rathore KS (2014) J Mol Catal A Chem 394:244

    Article  CAS  Google Scholar 

  45. Hameed A, Zehra ST, Shah SJA, Khan KM, Alharthy RD, Furtmann N, Bajorath J, Tahir Muhammad N, Iqbal J (2015) Chem Biol Drug Des 86:1115

    Article  CAS  PubMed  Google Scholar 

  46. Clapp RC, Clark JH, English JP, Fellows CE, Grotz RE, Shepherd RG (1952) J Am Chem Soc 74:1989

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to acknowledge financial support provided by Persian Gulf University for carrying out this research and also are grateful to Prof. H. Eslami for his valuable comments.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran

    Azar Jamaledini, Mohammad Reza Mohammadizadeh & S. Hekmat Mousavi

  2. Oil and Gas Research Center, Persian Gulf University, Bushehr, 75169, Iran

    Mohammad Reza Mohammadizadeh

Authors
  1. Azar Jamaledini
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Reza Mohammadizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Hekmat Mousavi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Reza Mohammadizadeh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 10595 kb)

Supplementary material 2 (PDF 5852 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jamaledini, A., Mohammadizadeh, M.R. & Mousavi, S.H. Catalyst-free, efficient, and green procedure for the synthesis of 5-heterocyclic substituted 6-aminouracils. Monatsh Chem 149, 1421–1428 (2018). https://doi.org/10.1007/s00706-018-2164-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2164-4

Keywords

Search

Navigation