Vitamin B12 used as effective biocatalyst for the synthesis of pyrano[2,3-c]cromenes and pyrano[2,3-d]pyrimidines
محورهای موضوعی : Iranian Journal of CatalysisGhasem Marandi 1 , Reyhaneh Nadernia 2 , Nourallah Hazeri 3 , Malek Taher Maghsoodlou 4
1 - Organic Chemistry Department, Faculty of Chemistry, Urmia University, Urmia, Iran
2 - Chemistry Department, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran
3 - Chemistry Department, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran
4 - Chemistry Department, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran
کلید واژه: Aldehydes, Vitamin B12, Biocatalyst, Pyrano[2, 3-c]chromene, Pyrano[2, 3-d]pyrimidine, Green route,
چکیده مقاله :
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.
- B. Deshmukh, S.S. Patil, S.D. Jadhav, P.B. Pawar, Synth. Commun. 42 (2012) 1177–1183.
- Firoozeh, S. Rezazadeh, C. Izanloo C, J. Mex. Chem. Soc. 61 (2017) 241-249.
- Brahmachari, B. Banerjee, ACS Sustainable Chem. Eng. 2 (2014) 411-422.
- Dodangeh, M.T. Maghsoodlou, M. Kangani, F. Paymozd, N. Hazeri, J. Nutr. Food. Sci. 1 (2016) 1-7.
- Petrović, B. Mojsilović, Z.M. Bugarčić, J. Mol. Catal. A: Chem. 170 (2001) 267–269.
- E. Helliwell, G.L.Wheeler, K.C. Leptos, R.E. Goldstein, A.G. Smith, Mol. Biol. Evol. 28 (2011) 2921–2933.
- Shimakoshi, Y. Hisaeda, TCIMAIL 138 (2009) 2-11.
- W. Daisley, Limnol. Oceanogr. 14 (1969) 224-228.
- M.M. Salih, S. Satyanarayana, Afr. J. Pure Appl. Chem. 3 (2009) 170-176.
- Taharaa, K. Hisaeda, Green Chem. 13 (2011) 558-561.
- C. Heber, C.C. Heers, U.C. Ravens, Die Pharmazie 48 (1993) 537-541.
- C. Davoll, J.C. Clarke, F.E.C. Eislager, J. Med. Chem. 15 (1972) 837-839.
- 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.
- R. Bennett, C.J. Blankely, R.W. Fleming, R.D. Smith, T.D. Tessman, J. Med. Chem. 24 (1981) 382-389.
- D.C. Broom, J.L.C. Shim, G.L.C. Anderson, J. Org. Chem. 41 (1976) 1095-1099.
- Wisen, J. Androsavich, C.G. Evans, L. Chang, J.E. Gestwi Cki, Bioorg. Med. Chem. Lett. 18 (2008) 60–65.
- Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14 (2006) 4792–802
- 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.
- Seyyedi, F. Shirini, M. Safarpoor, N. Langarudi, RSC Adv. 6 (2016) 44630–44640.
- S. Patel, J.R. Avalani, D.K. Raval, J. Saudi Chem. Soc. 20 (2016) S401–S405.
- Nikoorazm, P. Moradi, N. Noori, J. Porous Mater. 27 (2020) 1159-1169.
- Moradi, M. Hajjami, New J. Chem. 45 (2021) 2981-2994.
- Nikoorazm, B. Tahmasbi, S. Gholami, P. Moradi, App. Organomet. Chem. 34 (2020) e5919.
- Atashkar, A. Rostami, H. Gholami, B. Tahmasbi, Res. Chem. Intermed. 41 (2015) 3675-3681.
- Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, Polyhedron 163 (2019) 98–107.
- Lashkari, F. Mohamadpour, M.T. Maghsoodlou, R. Heydari, N. Hazeri, Polycycl. Aromat. Comp. (2020) https://doi.org/10.1080/10406638.2020.1781205.
- Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48 (2007) 3299–3303.
- T. Khan, M. Lal, S. Ali, M.M. Khan, Tetrahedron Lett. 52 (2011) 5327–5332.
- Q. Shia, N. Wub, Q.Y. Zhuang, J. Chem. Res. (2008) 542-545.
- Esmaeilpour, J. Javidi, F. Dehghani, F.A. Nowroozi Dodeji, RSC Adv. 5 (2015) 26625–26633.
- M. Khurana, B. Nand, P. Saluja, Tetrahedron 66 (2010) 5637-5641.
- Mohammadi Ziarani, A. Abbasi, A. Badiei, Z. Aslani, E-Journal of Chemistry 8 (2011) 293-299.
- Wanga, D. Shi, Q. Zhuanga, X. Wanga, H. Hud, J. Chem. Res. (2004) 818-820.
- Mohammadi Ziarani, A. Badiei, A. Azizi, M. Zarabadi, Iran. J. Chem. Chem. Eng. 30 (2011) 59-65.
- Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mo.l Catal. A: Chem. 359 (2012) 74-80.
- N. Elinson, F.V. Ryzhkov, V.M. Merkulova, A.I. Ilovaisky, G.I. Nikishin, Heterocycl. Commun. 20 (2014) 281-284.
- Seeliger, S. Berger, G.Y. Remennikov, K. Polborn, H. Mayr, J. Org. Chem. 72 (2007) 9170-9180.
- H. Zoorob, M.A. Elzahab, M. Abdel-Mogib, M.A. Ismail, M. Abdel-Hamid, Arzneim. Forsch Drug Res. 47 (1997) 958-962.
- Gao, S. Tu, T. Li, X. Zhang, S. Zhu, F. Fang, D. Shi, Synth. Commun. 34 (2004) 1295-1299.
- Azarifar, R. Nejat-Yami, F. Fatemeh Sameri, Z. Akrami, Lett. Org. Chem. 9 (2012) 435-439.
- Khazaei, A. Ranjbaran, F. Abbasi, M. Khazaei, A.R. Moosavi-Zare, RSC Adv. 5 (2015) 13643-13647.
- Wang, J.J. Ma, X. Zhou, X.H. Zang, Z. Wang, Y.J. Gao, P.L. Cui, Synth. Commun. 35 (2005) 2759-2764.
- J. Wang, J. Lu, Z. H. Zhang, Monatsh. Chem. 141 (2010) 1107–1112.
- Bararjanian, S. Balalaie, B. Movassagh, A. M. Amani, J. Iranian Chem. Soc. 6 (2009) 436–442.
- Pourghasemi‐Lati, F. Shirini, M. Alinia‐Asli, M. R. Rezvani, Appl. Organomet. Chem. 32 (2018) e4605.