Skip to main content

Advertisement

SpringerLink
Log in

Reaction of arylglyoxal hydrate derivatives with cyanoguanidine under benzilic rearrangement effect

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

Abstract

A novel series of (5-aryl-4-oxoimidazolidin-2-ylidene)cyanamides was successfully synthesized via the reaction of arylglyoxal hydrates with cyanoguanidine through benzilic rearrangement mechanism. The reaction was also optimized by changing various reaction factors for endeavor to increase the yield of the target product and reduce the by-product 1-cyano-3-(2-oxo-2-arylethylidene)guanidine formation.

Graphic 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. Javahershenas R, Khalafy J, Prager RH (2019) J Chem Rev 1:233

    Article  Google Scholar 

  2. Filimonov VD, Yusubov MS, Chi K-V (1998) Russ Chem Rev 67:725

    Article  Google Scholar 

  3. Riley HA, Gray AR (1935) Org Synth 15:67

    Article  Google Scholar 

  4. Khalafy J, Ezzati M, Madadi P, Marjani AP, Asl HY (2017) S Afr J Chem 70:132

    Article  CAS  Google Scholar 

  5. Young RM, Davies-Coleman MT (2011) Tetrahedron Lett 52:4036

    Article  CAS  Google Scholar 

  6. Tiecco M, Testaferri L, Tingoli M, Bartoli D (1990) J Org Chem 55:4523

    Article  CAS  Google Scholar 

  7. Yin G, Zhou B, Meng X, Wu A, Pan Y (2006) Org Lett 8:2245

    Article  CAS  PubMed  Google Scholar 

  8. Cao Z, Shi D, Qu Y, Tao C, Liu W, Yao G (2013) Molecules 18:15717

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Floyd MB, Du MT, Fabio PF, Jacob LA, Johnson BD (1985) J Org Chem 50:5022

    Article  CAS  Google Scholar 

  10. Karpov SV, Grigorev AA, Kayukov YS, Karpova IV, Nasakin OE, Tafeenko VA (2016) J Org Chem 81:6402

    Article  CAS  PubMed  Google Scholar 

  11. Lokhande PD, Waghmare SR, Gaikwad H, Hankare PP (2013) Indian J Chem 52B:300

    CAS  Google Scholar 

  12. Lokhande PD, Waghmare SR, Gaikwad H, Meshram SA, Hankare PP (2012) Int J Curr Res 4:199

    Google Scholar 

  13. Eftekhari-Sis B, Zirak M, Akbari A (2013) Chem Rev 113:2958

    Article  CAS  PubMed  Google Scholar 

  14. Mishra R, Panday AK, Choudhury LH, Pal J, Subramanian R, Verma A (2017) Eur J Org Chem 2017:2789

    Article  CAS  Google Scholar 

  15. Zhang G-N, Zhang M, Du X, Zhu M, Wang J, Shi D, Wang Y (2019) Heterocycles 98:535

    Article  CAS  Google Scholar 

  16. Gong J, Peshkov AA, Yu J, Amandykova S, Gimnkhan A, Huang J, Kashtanov S, Pereshivko OP, Peshkov VA (2020) RSC Adv 10:10113

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Tan X-F, Zhang F-G, Ma J-A (2020) Beilstein J Org Chem 16:638

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Chang X, Yang X, Chen Z, Zhong W (2019) Synlett 30:1431

    Article  CAS  Google Scholar 

  19. Heidari M, Anary-Abbasinejad M, Ghazanfari D, Akhgar MR (2018) Lett Org Chem 15:773

    Article  CAS  Google Scholar 

  20. Alizadeh-Bami F, Mehrabi H, Ranjbar-Karimi R (2019) J Sulfur Chem 40:469

    Article  CAS  Google Scholar 

  21. Shu W-M, Ma J-R, Zheng K-L, Sun H-Y, Wang M, Yang Y, Wu A-X (2014) Tetrahedron 70:9321

    Article  CAS  Google Scholar 

  22. Bandyopadhyay D, Smith LC, Garcia DR, Yadav RN, Banik BK (2014) Org Med Chem Lett 4:9

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  23. Kolos NN, Chechina NV, Zamigailo LL, Vashchenko EV (2013) Chem Heterocycl Compd 49:872

    Article  CAS  Google Scholar 

  24. Madhavachary R, Zarganes-Tzitzikas T, Patil P, Kurpiewska K, Kalinowska-Tłuścik J, Dömling A (2018) ACS Comb Sci 20:192

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Bayat M, Nasri S, Notash B (2017) Tetrahedron 73:1522

    Article  CAS  Google Scholar 

  26. Khalafy J, Rimaz M, Farajzadeh S, Ezzati M (2013) S Afr J Chem 66:179

    CAS  Google Scholar 

  27. Rimaz M, Khalafy J (2010) ARKIVOC 2010:110

    Google Scholar 

  28. Anary-Abbasinejad M, Jaafari M, Talebizadeh M (2019) Org Chem Res 5:139

    Google Scholar 

  29. Jiang B, Ye Q, Fan W, Wang S-L, Tu S-J, Li G (2014) Chem Commun 50:6108

    Article  CAS  Google Scholar 

  30. Jiang B, Fan W, Sun M-Y, Ye Q, Wang S-L, Tu S-J, Li G (2014) J Org Chem 79:5258

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Kolos NN, Kibkalo BV, Zamigaylo LL, Omelchenko IV, Shishkin OV (2015) Russ Chem Bull 64:864

    Article  CAS  Google Scholar 

  32. Khalafy J, Etivand N, Marjani AP, Khalillou N (2019) J Heterocycl Chem 56:1857

    Article  CAS  Google Scholar 

  33. Tu XJ, Hao WJ, Ye Q, Wang S-S, Jiang B, Li G, Tu S-J (2014) J Org Chem 79:11110

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Khalafy J, Rimaz M, Panahi L, Rabiei H (2011) Bull Korean Chem Soc 32:2428

    Article  CAS  Google Scholar 

  35. Modugu NR, Pittala PK (2017) Tetrahedron Lett 58:3859

    Article  CAS  Google Scholar 

  36. Javahershenas R, Khalafy J (2018) Asian J Green Chem 2:318

    CAS  Google Scholar 

  37. Nandwana NK, Patel Om PS, Srivathsa MR, Kumar A (2019) ACS Omega 4:10140

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Khodabakhshi S, Karami B, Eskandari K, Farahi M (2014) Tetrahedron Lett 55:3753

    Article  CAS  Google Scholar 

  39. Bardasov IN, Kayukova OV, Kayukov YaS, Ershov OV, Nasakin OE, Tafeenko VA (2009) Russ J Org Chem 45:1325

  40. Nouri A, Marjani AP, Khalafy J (2019) J Heterocycl Chem 56:2912

    Article  CAS  Google Scholar 

  41. Poursattar Marjani A, Ebrahimi Saatluo B, Nouri F (2018) Iran J Chem Chem Eng 37:149

    CAS  Google Scholar 

  42. Rezaei M, Bayat M, Notash B (2020) J Heterocycl Chem 57:880

    Article  CAS  Google Scholar 

  43. Rayudu SV, Karmakar D, Kumar P (2019) Tetrahedron Lett 60:151025

  44. Jiang B, Li Y, Tu M-S, Wang S-L, Tu S-J, Li G (2012) J Org Chem 77:7497

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  45. Moustafa AH, Amer AA (2018) Tetrahedron 74:324

    Article  CAS  Google Scholar 

  46. Prakash N, Elamaran M, Ingarsal N (2015) Chem Sci Trans 4:94

    Google Scholar 

  47. Moustafa AH, Shestakov AS, Potapov AYu, Romanov PS, Stolpovskaya NV, Shikhaliev KhS, Krugovov DA (2012) Vestnik VSU, Series: Chem Biol Pharm 2:55

  48. Amer AA, Moustafa AH (2017) Mol Divers 21:875

    Article  CAS  PubMed  Google Scholar 

  49. Hussein BRM, Moustafa AH (2019) Synth Commun 49:2401

    Article  CAS  Google Scholar 

  50. Moustafa AH, Amer AA (2017) Monatsh Chem 148:2129

    Article  CAS  Google Scholar 

  51. Fesenkoa AA, Shutalev AD (2020) Tetrahedron 76:131340

  52. Shutalev AD, Fesenko AA (2011) Tetrahedron 67:6883

    Article  CAS  Google Scholar 

  53. Takimoto M, Ebisuno T, Shiba R (1983) Bull Chem Soc Jpn 56:3319

    Article  CAS  Google Scholar 

  54. Solovyev PA, Shutalev AD (2009) Chem Heterocycl Compds 45:809

    Article  CAS  Google Scholar 

  55. Lambert DM, Masereel B, Gallez B, Geurts M, Scriba GKE (1996) J Pharm Sci 85:1077

    Article  CAS  PubMed  Google Scholar 

  56. Call L (1970) Monatsh Chem 101:344

    Article  CAS  Google Scholar 

  57. Birtwell S (1953) J Chem Soc 1953:1725

    Article  Google Scholar 

  58. Grytsai O, Druzhenko T, Demange L, Ronco C, Benhida R (2018) Tetrahedron Lett 59:164

    Article  CAS  Google Scholar 

  59. Soliman AM, Mohamed ShK, El-Remaily MAAA, Abdel-Ghany H (2014) J Heterocycl Chem 51:1322

    Article  CAS  Google Scholar 

  60. Dolzhenko AV, Foo MC, Tan BJ, Dolzhenko AV, Chiu GNC, Chui WK (2009) Heterocycles 78:1761

    Article  CAS  Google Scholar 

  61. Kosasayama A, Konno T, Higashi k, Ishikawa F (1979) Chem Pharm Bull 27:841

  62. Kreutzberger A, Sellheim M (1985) J Heterocycl Chem 22:721

    Article  CAS  Google Scholar 

  63. Moustafa AH, Ahmed WW, Khodairy A (2017) J Heterocycl Chem 54:3490

    Article  CAS  Google Scholar 

  64. Albayati MR, Mohamed MFA, Moustafa AH (2020) Synth Commun 50:1217

    Article  CAS  Google Scholar 

  65. Shestakov AS, Moustafa AH, Bushmarinov IS, Goloveshkin AS, Shapovalov AV, Shikhaliev KhS, Prezent MA, Sidorenko OE (2017) J Heterocycl Chem 54:551

    Article  CAS  Google Scholar 

  66. Paul S, Gupta M, Gupta R, Loupy A (2002) Synthesis 1:75

    Google Scholar 

  67. Joshi KC, Pathak VN, Goyal MK (1981) J Heterocycl Chem 18:1651

    Article  CAS  Google Scholar 

  68. Putnam TJ, Merrit HH (1937) Science 85:525

    Article  CAS  PubMed  Google Scholar 

  69. Krall RL, Penry JK, White BG, Kupferberg HJ, Swinyard EA (1978) Epilepsia 19:409

    Article  CAS  PubMed  Google Scholar 

  70. Bac P, Maurois P, Dupont C, Pages N, Stables JP, Gressens P, Evrard P, Vamecq J (1998) J Neurosci 18:4363

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. Bardovskyi R, Grytsai O, Ronco C, Benhid R (2020) New J Chem 44:8171

    Article  CAS  Google Scholar 

  72. Cheung S-T, Fonda ML (1979) Biochem Biophys Res Commun 90:940

    Article  CAS  PubMed  Google Scholar 

  73. Dunnavant WR, James FL (1956) J Am Chem Soc 78:2740

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt

    Amr H. Moustafa & Bahgat R. M. Hussein

Authors
  1. Amr H. Moustafa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bahgat R. M. Hussein
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bahgat R. M. Hussein.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1816 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Moustafa, A.H., Hussein, B.R.M. Reaction of arylglyoxal hydrate derivatives with cyanoguanidine under benzilic rearrangement effect. Monatsh Chem 152, 1285–1290 (2021). https://doi.org/10.1007/s00706-021-02838-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02838-z

Keywords

Search

Navigation