Green one-pot three-component synthesis of 4H-chromenes in the presence of nano-kaoline/BF3/Fe3O4 as a super paramagnetic nanocatalyst

Document Type : Article

Authors

1 Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I.R. Iran

2 Department of Organic Chemistry, Faculty of Chemistry, Yazd University, Yazd, I.R. Iran

Abstract

Fused benzo-4H-pyran, namely, 4H-chromene moiety is the leading formation block of several heter-ocyclic natural products with biological activity such as, antioxidant, antibacterial, antiviral, antifun-gal, hypotensive, diuretic, and antiallergenic, antileishmanial, anticoagulant and antitumor. Herein, one-pot three components of aldehyde, malononitrile and enolizable compounds in the presence of nano-kaoline/BFn/Fe3O4 catalytic system to improve the 4H-chromenes via domino Knoevenagel-Michael-cyclization coupling reaction is reported. The advantages of this protocol involve high yield of products, use of solvent-free condition, easy experimental work-up system, low reaction times, re-cyclable catalyst and green process which privilege it as an alternative for other analogous synthetic procedures. The structure of synthesized 4H-chromenes were elucidated by FT-IR, 1H NMR and 13C NMR.

Keywords


References:
1. Jiang, Y., Xu, K., and Zeng, C. "Use of electrochemistry in the synthesis of heterocyclic structures", Chem. Rev., 118(9), pp. 4485-4540 (2018).
2. Montazeri, N. "Antibacterial activity and efficient synthesis of 3,4-dihydropyrano[c]chromene derivatives by using ammonium tri uoroacetate (CF3COONH4) catalyst", Iran J. Med. Microbiol., 11(2), pp. 61-68 (2017).
3. Isaac, G., Marques-Lopez, E., and Raquel, P. "Herrera enantioselective organocatalyzed synthesis of 2-amino-3-cyano-4H-chromene derivatives", Symmetry, 7, pp. 1519-1535 (2015).
4. Bahmachari, G. and Banerjee, B. "Facile and one-pot access to diverse and densely functionalized 2-amino- 3-cyano-4H-pyrans and pyran-annulated heterocyclic scaffolds via an eco-friendly multicomponent reaction at room temperature using urea as a novel organocatalyst", ACS Sustainable Chem. Eng., 2, pp. 411- 422 (2013).
5. Hekmatshoar, R., Majedi, S., and Bakhtiari, K. "Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo [b] pyran derivatives", Catal. Commun., 9(2), pp. 307-310 (2008).
6. Maleki, B. and Sheikh, S. "One-pot synthesis of 2-amino-2-chromene and 2-amino-3-cyano-4H-pyran derivatives promoted by potassium  fluoride", Org. Prep. Proced. Int., 47(5), pp. 368-378 (2015).
7. Muthu, T., Anand, K., and Sureshkumar, M. "Ecofriendly approach: Graphene like boron nitride modified calcium material for the synthesis of 2-amino-4Hpyran-3-carbonitrile derivatives", Adv. Mater. Lett., 7(10), pp. 790-794 (2016).
8. Baghbanian, S.M., Rezaei, N., and Tashakkorian, H. "Nanozeolite clinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino- 4 H-chromene derivatives in aqueous media", Green Chem., 15(12), pp. 3446-3458 (2013).
9. Esmaeilpour, M., Javidi, J., Dehghani, F., and Nowroozi Dodeji, F. "A green one-pot threecomponent synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives using a Fe3O4@SiO2-imid-PMAn magnetic nanocatalyst under ultrasonic irradiation or reflux conditions", RSC Adv., 5(34), pp. 26625-26633 (2015).
10. Safaei-Ghomi, J., Javidan, A., Ziarati, A., and Shahbazi-Alavi, H. "Synthesis of new 2-amino-4Hpyran- 3,5-dicarboxylate derivatives using nanocrystalline MIIZr4(PO4)6 ceramics as reusable and robust catalysts under microwave irradiation", J. Nanopart. Res., 17(8), pp. 338-343 (2015).
11. Kiani, M., Mohammadipour, M., and Zamanian, A. "Design, preparation and characterization of MoO3Hfunctionalized Fe3O4@SiO2 magnetic nanocatalyst and application for the one-pot multicomponent reactions", Acta Chim. Slov., 64(3), pp. 707-713 (2017).
12. Albadi, J., Razeghi, A., Mansournezhad, A., and Azarian, Z. "CuO-CeO2 nanocomposite catalyzed efficient synthesis of aminochromenes", J. Nanostruct. Chem., 3(1), pp. 85-89 (2013).
13. Gupta, R., Ladage, S., and Ravishankar, L. "Mg-Al hydrotalcite catalyzed efficient one-pot synthesis of 4- benzo[b]pyrans, 2-aryl benzimidazole and 2-aryl-4, 5- dihydro-1H-imidazole derivatives", Chem. J., 1, pp. 5-9 (2015).
14. Tabassum, S., Govindaraju, S., and Pasha, M.A. "Ultrasound mediated, iodine catalyzed green synthesis of novel 2-amino-3-cyano-4H-pyran derivatives", Ultrason Sonochem., 24, pp. 1-7 (2015).
15. Robabeh, B. and Shariati, S.A.N. "Green synthesis of 2-amino-3-cyano-4H-chromenes in water using nano silica-bonded 5-N-propyl-octahydro-pyrtmido [1,2-4] azepinium chloride as an effective and reusable nano catalyst", J. Chil. Chem. Soc., 60(2), pp. 2900-2904 (2015).
16. Niknam, K., Khataminejad, M., and Zeyaei, F. "Diethylene glycol-bis(3-methylimidazolium) dihydroxide as a dicationic ionic liquid catalyst for the synthesis of 4H-pyrane derivatives in aqueous medium", Tetrahedron Lett., 57, pp. 361-365 (2016).
17. Rostamnia, S., Nuri, A., Xin, H., Pourjavadi, A., and Hosseini, S.H. "Water dispersed magnetic nanoparticles (H2O-DMNPs) of -Fe2O3 for multicomponent coupling reactions: a green, single-pot technique for the synthesis of tetrahydro-4H-chromenes and hexahydroquinoline carboxylates", Tetrahedron Lett., 54(26), pp. 3344-3347 (2013).
18. Mirjalili, B.F. and Dehghani Tafti, M. "Synthesis of quinoxalines promoted by eco-friendly nanokaoline/ BF3/Fe3O4 nano-catalyst under grinding condition", Scientia Iranica, C, 24, pp. 3014-3020 (2017).
19. Guo, R.Y., An, Z.M., Mo, L.P., Wang, R.Z., Liu, H.X., Wang, S.X., and Zhang, Z.H. "Meglumine: A novel and efficient catalyst for one-pot, three-component combinatorial synthesis of functionalized 2-amino-4Hpyrans", ACS Comb. Sci., 15(11), pp. 557-563 (2013).
20. Dekamin, M.G., Peyman, S.Z., Karimi, Z., Javanshir, S., Naimi-Jamal, M.R., and Barikani, M. "Sodium alginate: An efficient biopolymeric catalyst for green synthesis of 2-amino-4H-pyran derivatives", Inter. J. Bio. Macromol., 87, pp. 172-179 (2016).
21. Kaur, M., Kaur, A., Mankotia, S., Singh, H., Singh, A., Singh, J.V., Gupta, M.K., Sharma, S., Nepali, K., and Singh Bedi, P.M. "Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine derivatives as xanthine oxidase inhibitor", Eur. J. Med. Chem., 131, pp. 14- 28 (2017).
22. Goli-Jolodar, O., Shirini, F., and Seddighi, M. "An efficient and practical synthesis of specially 2-amino-4Hpyrans catalyzed by C4(DABCO-SO3H)2.4Cl", Dyes and Pigments, 133, pp. 292-303 (2016).
23. Bhaskar, K.V., Joshi, S.D., and Ahuja, P. "A facile and one-pot synthesis of pyrone derivatives via ionic liquid catalysed knoevenagel reaction and their biological evaluation", Indian J. Heterocycl. Chem., 25(3-4), pp. 225-230 (2016).
24. Zolfigol, M.A., Yarie, M., Baghery, S., Khoshnood, A., and Alonso, D.A. "1H-imidazol-3-ium tricyanomethanide f[HIM]C(CN)3g as a nanostructured molten salt catalyst: application to the synthesis of pyrano[4,3-]pyrans", Res. Chem. Intermed., 43(5), pp. 3291-3305 (2017).
25. Mohammadi, R., Esmati, S., Gholamhosseini-Nazari, M., and Teimuri-Mofrad, R. "Synthesis and characterization of a novel Fe3O4@SiO2-BenzIm-Fc[Cl]/BiOCl nano-composite and its efficient catalytic activity in the ultrasound-assisted synthesis of diverse chromene analogs", New J. Chem., 43(1), pp. 135-145 (2019).
Volume 27, Issue 3
Transactions on Chemistry and Chemical Engineering (C)
June 2020
Pages 1216-1225
  • Receive Date: 08 August 2019
  • Revise Date: 26 January 2020
  • Accept Date: 20 April 2020