Vitamin B12 used as effective biocatalyst for the synthesis of pyrano[2,3-c]cromenes and pyrano[2,3-d]pyrimidines

Document Type : Articles

Authors

1 Organic Chemistry Department, Faculty of Chemistry, Urmia University, Urmia, Iran

2 Chemistry Department, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran

Abstract

Synthesis of organic compounds using some natural compounds as catalysts has gained more attention in recent decades. With respect to the importance of these procedures, the synthesis of 3,4-dihydropyrano[2,3-c]chromene and pyrano[2,3-d]pyrimidine derivatives using vitamin B12 by a one-pot reaction of malononitrile, benzaldehydes and 4-hydroxycumarine or 1,3-dimethylbarbituric acid is reported.

Graphical Abstract

Vitamin B12 used as effective biocatalyst for the synthesis of pyrano[2,3-c]cromenes and pyrano[2,3-d]pyrimidines

Keywords


  1. B. Deshmukh, S.S. Patil, S.D. Jadhav, P.B. Pawar, Synth. Commun. 42 (2012) 1177–1183.
  2. Firoozeh, S. Rezazadeh, C. Izanloo C, J. Mex. Chem. Soc. 61 (2017) 241-249.
  3. Brahmachari, B. Banerjee, ACS Sustainable Chem. Eng. 2 (2014) 411-422.
  4. Dodangeh, M.T. Maghsoodlou, M. Kangani, F. Paymozd, N. Hazeri, J. Nutr. Food. Sci. 1 (2016) 1-7.
  5. Petrović, B. Mojsilović, Z.M. Bugarčić, J. Mol. Catal. A: Chem. 170 (2001) 267–269.
  6. E. Helliwell, G.L.Wheeler, K.C. Leptos, R.E. Goldstein, A.G. Smith, Mol. Biol. Evol. 28 (2011) 2921–2933.
  7. Shimakoshi, Y. Hisaeda, TCIMAIL 138 (2009) 2-11.
  8. W. Daisley, Limnol. Oceanogr. 14 (1969) 224-228.
  9. M.M. Salih, S. Satyanarayana, Afr. J. Pure Appl. Chem. 3 (2009) 170-176.
  10. Taharaa, K. Hisaeda, Green Chem. 13 (2011) 558-561.
  11. C. Heber, C.C. Heers, U.C. Ravens, Die Pharmazie 48 (1993) 537-541.
  12. C. Davoll, J.C. Clarke, F.E.C. Eislager, J. Med. Chem. 15 (1972) 837-839.
  13. H. Shamroukh, M.E.A. Zaki, E.M.H. Morsy, F.M.E. Abdel Motti, F.M. Abdel Megeid, Arch. Pharm. 340 (2007) 236-243.
  14. R. Bennett, C.J. Blankely, R.W. Fleming, R.D. Smith, T.D. Tessman, J. Med. Chem. 24 (1981) 382-389.
  15. D.C. Broom, J.L.C. Shim, G.L.C. Anderson, J. Org. Chem. 41 (1976) 1095-1099.
  16. Wisen, J. Androsavich, C.G. Evans, L. Chang, J.E. Gestwi Cki, Bioorg. Med. Chem. Lett. 18 (2008) 60–65.
  17. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14 (2006) 4792–802
  18. Biot, G. Glorian, L.A. Maciejewski, J.S. Brocard, O. Domarle, G. Blampain, P. Blampain, A.J. Georges, H. Abessolo, D. Dive, J. Lebibi, J. Med. Chem. 40 (1997) 3715–3718.
  19. Seyyedi, F. Shirini, M. Safarpoor, N. Langarudi, RSC Adv. 6 (2016) 44630–44640.
  20. S. Patel, J.R. Avalani, D.K. Raval, J. Saudi Chem. Soc. 20 (2016) S401–S405.
  21. Nikoorazm, P. Moradi, N. Noori, J. Porous Mater. 27 (2020) 1159-1169.
  22. Moradi, M. Hajjami, New J. Chem. 45 (2021) 2981-2994.
  23. Nikoorazm, B. Tahmasbi, S. Gholami, P. Moradi, App. Organomet. Chem. 34 (2020) e5919.
  24. Atashkar, A. Rostami, H. Gholami, B. Tahmasbi, Res. Chem. Intermed. 41 (2015) 3675-3681.
  25. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, Polyhedron 163 (2019) 98–107.
  26. Lashkari, F. Mohamadpour, M.T. Maghsoodlou, R. Heydari, N. Hazeri, Polycycl. Aromat. Comp. (2020) https://doi.org/10.1080/10406638.2020.1781205.
  27. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48 (2007) 3299–3303.
  28. T. Khan, M. Lal, S. Ali, M.M. Khan, Tetrahedron Lett. 52 (2011) 5327–5332.
  29. Q. Shia, N. Wub, Q.Y. Zhuang, J. Chem. Res. (2008) 542-545.
  30. Esmaeilpour, J. Javidi, F. Dehghani, F.A. Nowroozi Dodeji, RSC Adv. 5 (2015) 26625–26633.
  31. M. Khurana, B. Nand, P. Saluja, Tetrahedron 66 (2010) 5637-5641.
  32. Mohammadi Ziarani, A. Abbasi, A. Badiei, Z. Aslani, E-Journal of Chemistry 8 (2011) 293-299.
  33. Wanga, D. Shi, Q. Zhuanga, X. Wanga, H. Hud, J. Chem. Res. (2004) 818-820.
  34. Mohammadi Ziarani, A. Badiei, A. Azizi, M. Zarabadi, Iran. J. Chem. Chem. Eng. 30 (2011) 59-65.
  35. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mo.l Catal. A: Chem. 359 (2012) 74-80.
  36. N. Elinson, F.V. Ryzhkov, V.M. Merkulova, A.I. Ilovaisky, G.I. Nikishin, Heterocycl. Commun. 20 (2014) 281-284.
  37. Seeliger, S. Berger, G.Y. Remennikov, K. Polborn, H. Mayr, J. Org. Chem. 72 (2007) 9170-9180.
  38. H. Zoorob, M.A. Elzahab, M. Abdel-Mogib, M.A. Ismail, M. Abdel-Hamid, Arzneim. Forsch Drug Res. 47 (1997) 958-962.
  39. Gao, S. Tu, T. Li, X. Zhang, S. Zhu, F. Fang, D. Shi, Synth. Commun. 34 (2004) 1295-1299.
  40. Azarifar, R. Nejat-Yami, F. Fatemeh Sameri, Z. Akrami, Lett. Org. Chem. 9 (2012) 435-439.
  41. Khazaei, A. Ranjbaran, F. Abbasi, M. Khazaei, A.R. Moosavi-Zare, RSC Adv. 5 (2015) 13643-13647.
  42. Wang, J.J. Ma, X. Zhou, X.H. Zang, Z. Wang, Y.J. Gao, P.L. Cui, Synth. Commun. 35 (2005) 2759-2764.
  43. J. Wang, J. Lu, Z. H. Zhang, Monatsh. Chem. 141 (2010) 1107–1112.
  44. Bararjanian, S. Balalaie, B. Movassagh, A. M. Amani, J. Iranian Chem. Soc. 6 (2009) 436–442.
  45. Pourghasemi‐Lati, F. Shirini, M. Alinia‐Asli, M. R. Rezvani, Appl. Organomet. Chem. 32 (2018) e4605.