Iranian Journal of Chemistry

Iranian Journal of Chemistry

Green and one-pot synthesis of pyrimidopyrimidines derivatives in the presence of natural chromite ore catalyst in aqueous media

Document Type : Original Article

Authors
Osman Shanavazi
Enayatollah Sheikhhosseini
Department of Chemistry, Kerman Branch, Islamic Azad University, Kerman, Iran.
10.22036/cr.2021.304733.1157
Abstract
The maim elements of chromite ore were deduced by X-ray fluorescence (XRF) after collection and grinding. The presence of irregular designs in the form of cavities with size of 50 to 200 micrometers and sometimes nanometers in the structure of this catalyst using solid surface morphology with SEM and TEM electron micrograph scanning was confirmed. In a one-pot three component reaction of diver's aromatic aldehydes, barbituric acid and urea or thiourea, pyrimidopyrimidine (5 , 6 –dihydro – 5 – aryl pyrimido [4 , 5 - d] pyrimidine – 2 , 4 , 7 (1H , 3H , 8H ) - trione) heterocyclic products were prepared in the presence of chromite ore as natural catalyst. There was no need for the column purification of the products in these reactions. Moreover, this methodology offered several advantages such as good yields, simple procedure and simple purification steps. Using water as solvent made the process environmentally and economically benign.

Graphical Abstract

Green and one-pot synthesis of pyrimidopyrimidines derivatives in the presence of natural chromite ore catalyst in aqueous media
Keywords
Chromite ore
Green synthesis
Multi-component reaction
Natural catalyst
Pyrimidopyrimidine
  1. I. Ugi, A. Domling, W. Horl, Endeavour, 18, 115 (1994).
  2. X. Corte, E.M. Marigorta, F. Palacios, F. Vicario, Molecules, 24, 2951 (2019).
  3. L. M. Ramos, M. O. Rodrigues, B. A. D. Neto, Org. Biomol. Chem., 17, 7260 (2019).
  4. J. Wiemann, L. Fischer, J. Kessler, D. Strohl, R. Csuk, Bioorg. Chem., 81, 567 (2018).
  5. H. G. O. Alvim, J. R. Correa, J. A. F. Assumpcao, W. A. Silva, M. O. Rodrigues, J. L. Macedo, M. Fioramonte, F. C. Gozzo, C. C. Gatto, B. A. D. Neto, J. Org. Chem., 83, 4044 (2018).
  6. M. Konstantinidou, K. Kurpiewska, J. Kalinowska-Tluscik, A. Domling, Eur. J. Org Chem., 47, 6714 (2018).
  7. I. M. Lagoja, Chem. Biodivers., 2, 1 (2005).
  8. H. Kakiya, K. Yagi, H. Shinokubo, J. Am. Chem. Soc., 124, 9032 (2002).
  9. M. Movassaghi, M. D. Hill, J. Am. Chem. Soc., 128, 14254, (2006).
  10. V. S. Dinakaran, B. Bomma, K. K. Srinivasan, Pharm. Chem., 4, 255 (2012).
  11. D. Prajapati, M. Gohain, A. Thakur, J. Bioorg. Med. Chem. Lett., 16, 3537 (2006).
  12. T. Venkatesh, Y. D. Bodke, S. J. A. Rao, Chemical Data Collections, 25, 100335 (2020).
  13. A. M. Hussein, J. Saud. Chem. Soc., 14, 61 (2010).
  14. E. C. Taylor, R. J. Knopf, R. F. Meyer, A. Holmes, M. L. Hoefle, J. Am. Chem. Soc., 82, 5711 (1962).
  15. N. Kitamura, A. Onishi, Chem. Abstr., 104, 186439 (1984).
  16. P. Sharma, N. Rane, V. K. Gurram, Bioorg. Med. Chem. Lett., 14, 4185 (2004).
  17. A. Y. Aksinenko, T. V. Goreva, T. A. Epishina, S. V. Trepalin, V. B. Sokolov. J. Fluor. Chem., 188, 191 (2016).
  18. Y. Fang, J. Xu, Z. Li, Z. Yang, L. Xiong, Y. Jin, Q. Wang, S. Xie, W. Zhu, S. Chang, Bioorg. Med. Chem., 26, 4080 (2018).
  19. Y. Diaoa, X. Fang, P. Song, M. Lai, L.Tong, Y. Hao, D. Dou, Y. Liu, J. Ding, Z. Zhao, H. Xieb, H. Li, Bioorg. Med. Chem., 27, 3390 (2019).
  20. S. Badvel, R. R. Gopireddy, T. B. Shaik, S. Hasti, V. R. Tummaluru, N. R. Chamarthi, Chem. Heterocycl. Compd., 51, 749 (2015).
  21. A. Sheykhi-Estalkhjani, N.O. Mahmoodi, A. Yahyazadeh, M. P. Nadamani, H. T. Nahzomi, Tetrahedron, 75, 749 (2019).
  22. S. V. Shinde, W. N. Jadhav, N. N. Karade, Orient. J. Chem., 26, 307 (2010).
  23. R. Gupta, A. Jain, R. Joshi, M. Jain, Bull. Korean Chem. Soc., 32, 899 (2011).
  24. F. M. Moghaddam, M. R. Khodabakhshi, M. Aminaee, Tetrahedron Lett., 55, 4720 (2014).
  25. J. P. D. Cruz, T. C. G. Ortega, F. S. D. Cuesta, Lipids, 27, 192 (1992).
  26. S. Majumder, P. Borah, P. J-Bhuyan, Tetrahedron Lett., 55, 1168 (2014).
  27. R. Ghorbani‐Vaghei, N. Sarmast, Appl. Organomet. Chem., 32, 4003 (2017).
  28. A. Mobinikhaledi, T. Mosleh, N. Foroughifar, Res. Chem. Intermed., 41, 2985 (2015).
  29. S. Badvel, R. Gopireddy, T. Shaik, S. Hasti, V. Tummaluru, N. Chamarthi, Chem. Heterocycl. Compd., 51, 749 (2015).
  30. M. H. Abdollahi-Basir, F. Shirini, H. Tajik, M. A. Ghasemzadeh, J. Mol. Struct., 1197, 318 (2019).
  31. M. Kidwai, K. Singhal, S. Kukreja, Z. Naturforsch, 62b, 732 (2007).
  32. M. R. Bhosle, L. D. Khillare, J. R. Mali, A. P. Sarkate, D. K. Lokwani, S. V. Tiwari, New J. Chem., 42, 18621 (2018).
  33. K. Hirota, Y. Kitade, H. Sajiki, Y. Maki, Synthesis, 589 (1984).
  34. R. Bakhshali-Dehkordi, M. A. Ghasemzadeh, J. Safaei-Ghomi, J. Mol. Struct., (2020-in press)
  35. ز. لاسمی، ب. صادقی، مجله علمی و پژوهشی شیمی کاربردی، شماره 55، 149، (1399)
  36. م. مکثایی، ع. شیخ حسینی، نشریه شیمی و مهندسی شیمی، شماره 1، 93 (1396).
  37. E. Sheikhhosseini, T. S. Mokhtari, M. Faryabi, A. Rafiepour, S. Soltaninejad. Iranian J. Chem & Chem. Eng., 35, 43 (2016).
  38. A. H. Kategaonkar, S. A. Sadaphal, K. F. Shelke, B. B. Shingate, M. S. Shingare, Ukrainica Bioorganica Acta, 1, 3 (2009).
  39. M. A. A. Mohamed, N. F. H. Mahmoud, A. M. M. El-Saghier, Chemistry Journal, 2, 64 (2012)4.
  40. F. Shirini, M. S. N. Langarudi, N. Daneshvar, N. Jamasbi, M. Irankhah-Khanghah, J. Mol. Struct., 1161, 366 (2018).

  • Receive Date 15 September 2021
  • Revise Date 24 December 2021
  • Accept Date 29 December 2021