Abstract
A novel four-component approach for the synthesis of 1-phenyl-1,4-dihydro-2H-9-oxa-4-aza-phenanthrene-3,10-dione derivatives has been presented via the reaction of 4-hydroxycoumarin, ammonia solution, Meldrum’s acid and aromatic aldehydes. The products were characterized by FT-IR, 1HNMR, 13CNMR, CHN elemental analysis and mass spectroscopy. According to the obtained results, SBA-15-SO3H is considered as an efficient catalyst for the preparation of novel 4-aza-phenanthrene-3,10-dione derivatives.
Graphical Abstract
Similar content being viewed by others
References
J. Zhu, Q. Wang, M. X. Wang, eds. Multicomponent reactions in organic synthesis. (Wiley, Hoboken, 2014)
S. Brauch, S.S. Van Berkel, B. Westermann, Chem. Soc. Rev. 42(12), 4948–4962 (2013)
R.C. Cioc, E. Ruijter, R.V. Orru, Green Chem. 16(6), 2958–2975 (2014)
F.M. Kerton, R. Marriott, Alternative solvents for green chemistry (Royal Society of Chemistry, London, 2013)
A. Mondal, C. Mukhopadhyay, ACS comb. Sci. 17(7), 404–408 (2015)
P. Ravichandiran, B. Lai, Y. Gu, Chem. Rec. 17(2), 142–183 (2017)
C. Liu, L. Zhou, D. Jiang, Y. Gu, Asian J. Org. Chem. 5(3), 367–372 (2016)
A.S. Ivanov, Chem. Soc. Rev. 37(4), 789–811 (2008)
L. Rong, X. Li, H. Wang, D. Shi, S. Tu, Q. Zhuang, Synth. Commun. 37(2), 183–189 (2007)
M. Sabbaghan, I. Yavari, Z. Hossaini, Comb. Chem. High. Throughput Screen. 13(9), 813–817 (2010)
M.O. Noguez, V. Marcelino, H. Rodríguez, O. Martín, J.O. Martínez, G.A. Arroyo, F.J. Pérez, M. Suárez, R. Miranda, Int. J. Mol. Sci. 12, 2641–2649 (2011)
S. Tu, X. Zhu, J. Zhang, J. Xu, Y. Zhang, Q. Wang, R. Jia, B. Jiang, J. Zhang, C. Yao, Bioorg. Med. Chem. Lett. 16, 2925–2928 (2006)
D.P. Curran, H. Liu, J. Am. Chem. Soc. 114, 5863–5864 (1992)
R.J. Cox, D. O’Hagan, J. Chem. Soc. Perkin Trans 1, 2537–2540 (1991)
D. Williams, P. Lowder, Y.G. Gu, Tetrahedron Lett. 38, 327–330 (1997)
S. Brickner, Chem. Ind. 1997, 131–135 (1997)
A.P. Kozikowski, G. Campiani, L.Q. Sun, S. Wang, A. Saxena, B.P. Doctor, J. Am. Chem. Soc. 118, 11357–11362 (1996)
S.J. Saghanezhad, S. Sayyahi, Res. Chem. Intermed. 43, 2491–2500 (2017)
S. Rostamizadeh, L. Tahershamsi, N. Zekri, J. Iran. Chem. Soc. 12(8), 1381–1389 (2015)
Acknowledgements
We gratefully acknowledge the support of this work by Payame Noor University Research Council.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Sayahi, M.H., Saghanezhad, S.J. & Mahdavi, M. SBA-15-SO3H-assisted preparation of 4-aza-phenanthrene-3,10-dione derivatives via a one-pot, four-component reaction. Res Chem Intermed 44, 739–747 (2018). https://doi.org/10.1007/s11164-017-3131-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-017-3131-0