Abstract
In this research, nano-SiO2–H3BO3 is introduced as a novel environmentally benign and recyclable heterogeneous catalyst for the synthesis of aminonaphthols under solvent-free conditions without an additional co-catalyst or additive in air. This synthesis method offers several advantages, such as a green and eco-friendly protocol, operational simplicity, mild reaction conditions, short reaction times, higher yields and easy work-up procedures. The work-up of these very clean reactions involves only recrystallization of the product from ethanol and recovery of the catalyst by filtration. The catalyst can be reused several times without losing activity.
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C. Cardellicchio, M.A.M. Capozzi, F. Naso, Tetrahedron 21, 507–517 (2010)
I. Szatmári, F. Fülöp, Tetrahedron 69, 1255–1278 (2013)
M. Gerlach, C. Maul, US Patent 7,202,242 B2 (2007)
N. Gyemant, H. Engi, Z. Schelz, I. Szatmari, D. Toth, F. Fulop, J. Molnar, P. de Witte, Br. J. Cancer 103, 178–185 (2010)
A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 877–882 (1999)
I. Szatmari, A. Heteny, L. Lazar, F. Fulop, J. Heterocycl. Chem. 41, 367–373 (2004)
V.D. Dhakane, S.S. Gholap, U.P. Deshmukh, H.V. Chavan, B.P. Bandgar, C. R. Chim. 17, 431–436 (2014)
M. Heydenreich, A. Koch, S. Klod, I. Szatmari, F. Fulop, E. Kleinpeter, Tetrahedron 62, 11081–11089 (2006)
M. Ghandi, A. Olyaei, S. Raoufmoghaddam, J. Heterocycl. Chem. 46, 914–919 (2009)
I. Szatmari, T.A. Martinek, L. Lazar, A. Koch, E. Kleinpeter, K. Neuvonen, F. Fulop, J. Org. Chem. 69, 3645–3653 (2004)
H.V. Poel, G. Guilaumet, V.M. Massuard, Tetrahedron Lett. 43, 1205–1208 (2002)
P. Zang, E.A. Terefenko, A. Fensome, J. Wrobel, R. Winneker, Z. Zang, Bioorg. Med. Chem. Lett. 13, 1313–1316 (2003)
X. Xu, C. Wang, J. He, Y. Hu, H. Hu, Tetrahedron Lett. 43, 8367–8369 (2002)
M. Marinova, K. Kostova, P. Tzvetkova, M. Tavlinova-Kirilova, R. Nikolova, B. Shivachev, Tetrahedron Asymmetry 24, 1453–1466 (2013)
A.R. Katritzky, A.A.A. Abdel-Fattah, D.O. Tymoshenko, S.A. Belyakov, I. Ghiviriga, P.J. Steel, J. Org. Chem. 64, 6071–6075 (1999)
A. Shahrisa, S. Esmati, M. Gholomhosseini, Nazari. J. Chem. Sci. 124, 927–931 (2012)
N. Azizi, M. Edrisi, Res. Chem. Intermed. (2016). doi:10.1007/s11164-016-2628-2
H.R. Shaterian, A. Hosseinian, Res. Chem. Intermed. 40, 3011–3019 (2014)
H.R. Shaterian, A. Hosseinian, Res. Chem. Intermed. 41, 793–801 (2015)
N.L. Chavan, P.N. Naik, S.K. Nayak, R.S. Kusurkar, Synth. Commun. 40, 2941–2947 (2010)
H.R. Shaterian, H. Yarahmadi, M. Ghashang, Bioorg. Med. Chem. Lett. 18, 788–792 (2008)
A. Shahrisa, R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, Synlett 26, 1031–1038 (2015)
M.R. Saidi, N. Azizi, M.R. Naimi-Jamal, Tetrahedron Lett. 42, 8111–8113 (2001)
A. Kumar, M.K. Gupta, M. Kumar, Tetrahedron Lett. 51, 1582–1584 (2010)
B. Karmakar, J. Banerji, Tetrahedron Lett. 52, 4957–4960 (2011)
S.D. Dindulkar, V.G. Puranik, Y.T. Jeong, Tetrahedron Lett. 53, 4376–4438 (2012)
F. Janati, M.M. Heravi, A.M. Shokraie, Synth. React. Inorg. Met. Org. Chem. 45, 1–5 (2015)
S.R. Mistry, R.S. Joshi, K.C. Maheria, J. Chem. Sci. 123, 427–432 (2011)
H.R. Shaterian, H. Yarahmadi, M. Ghashang, Tetrahedron 64, 1263–1269 (2008)
J.S. Ghomi, S. Zahedi, Monatsh. Chem. 144, 687–693 (2013)
F. Moeinpour, N. Dorostkar-Ahmadi, A. Sardashti-Birjandi, A. Khojastehnezhad, M. Vafaei, Res. Chem. Intermed. 40, 3145–3152 (2014)
M.C.C. Azevedo, A.M.V. Cavaleiro, J. Chem. Edu. 89, 767–770 (2012)
D.G. Hall, Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd edn. (Wiley-VCH, Weinheim, 2011)
M.K. Chaudhuri, S. Hussain, M.L. Kantam, B. Neelima, Tetrahedron Lett. 46, 8329–8331 (2005)
S. Tu, F. Fang, C. Miao, H. Jiang, Y. Feng, Y. Shi, X. Wang, Tetrahedron Lett. 44, 6153–6155 (2003)
C. Mukhopadhyay, A. Datta, R.J. Butcher, Tetrahedron Lett. 50, 4246–4250 (2009)
X. Zhou, M.Y. Zhang, S.T. Gao, J.J. Ma, C. Wang, C. Liu, Chin. Chem. Lett. 20, 905–908 (2009)
H. Valizadeh, H. Gholipour, C. R. Chim. 14, 963–966 (2011)
Z. Karimi-Jaberi, M. Keshavarzi, Chin. Chem. Lett. 21, 547–549 (2010)
Z. Karimi-Jaberi, M. Amiri, Heteroat. Chem. 21, 96–98 (2010)
J.S. Kumar, S.C. Jonnalagadda, V.R. Mereddy, Tetrahedron Lett. 51, 779–782 (2010)
A. Shahrisa, R. Teimuri-Mofrad, M. Gholamhosseini-Nazari, Mol. Divers. 19, 87–101 (2014)
R. Teimuri-Mofrad, A. Shahrisa, M. Gholamhosseini-Nazari, N. Arsalani, Res. Chem. Intermed. 42, 3425–3439 (2016)
H.T. Lu, Colloid J. 75, 311–318 (2013)
J. Clark, Chem. Commun. 19, 2135–2136 (1998)
S.S. Ganesan, N. Rajendran, S.I. Sundarakumar, A. Ganesan, B. Pemiah, Synthesis 45, 1564–1568 (2013)
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The authors would like to acknowledge the financial support from the Iran National Science Foundation (INSF) and the University of Tabriz.
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Teimuri-Mofrad, R., Gholamhosseini-Nazari, M., Esmati, S. et al. An efficient and green method for the synthesis of Betti base employing nano-SiO2–H3BO3 as a novel recyclable heterogeneous catalyst. Res Chem Intermed 43, 6845–6861 (2017). https://doi.org/10.1007/s11164-017-3024-2
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DOI: https://doi.org/10.1007/s11164-017-3024-2