Nano-Fe₃O₄@silica sulfuric acid as a reusable and magnetically separable potent solid acid catalyst in Biginelli-type reaction for the one-pot multicomponent synthesis of fused dihydropyrimidine derivatives: A greener NOSE and SFRC approach

References

• Poliakoff, M.; Fitzpatrick, J. M.; Farren, T. R.; Anastas, P. T. Science 2002, 297, 807–810.
   PubMed Web of Science ®Google Scholar
• Sheldon, R. A. Chem. Soc. Rev. 2012, 41, 1437–1451.
   PubMed Web of Science ®Google Scholar
• Sheldon, R. A. Chem. Commun. 2008, 3352–3365.
   PubMed Web of Science ®Google Scholar
• Walsh, P. T.; Li, H.; de Parrodi, C. A. Chem. Rev. 2007, 107, 2503–2545.
   PubMed Web of Science ®Google Scholar
• Nasir Baig, R. B.; Varma, R. S. Chem. Commun. 2012, 48, 5853–5855.
   PubMed Web of Science ®Google Scholar
• Nasir Baig, R. B.; Varma, R. S. Chem. Soc. Rev. 2012, 41, 1559–1584.
   PubMed Web of Science ®Google Scholar
• Safari, J.; Zarnegar, Z. J. Mol. Catal. A: Chem. 2013, 379, 269–276.
   Web of Science ®Google Scholar
• Koukabi, N.; Kolvari, E.; Zolfigol, M. A.; Khazaei, A.; Shaghasemi, B. S.; Fasahatib, B. Adv. Synth. Catal. 2012, 354, 2001–2008.
   Web of Science ®Google Scholar
• Rostamnia, S.; Nuri, A.; Xin, H.; Pourjavadi, A.; Hosseini, S. H. Tetrahedron Lett. 2013, 54, 3344–3347.
   Web of Science ®Google Scholar
• Zheng, X.; Luo, S.; Zhang, L.; Cheng, J. P. Green Chem. 2009, 11, 455–458.
   Web of Science ®Google Scholar
• Thomson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555–600.
   PubMed Web of Science ®Google Scholar
• Weber, L.; Lilgen, K.; Almsteher, N. Synlett 1999, 3, 366–374.
   Web of Science ®Google Scholar
• Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Tetrahedron Lett. 2003, 44, 6497–6499.
   Web of Science ®Google Scholar
• Yarim, M.; Sarac, S.; Kilic, F. S.; Erol, K. Farmaco 2002, 58, 17–24.
   Google Scholar
• Byk, G.; Gettlieb, H. E.; Herscovici, J.; Mirkin, F. J. Comb. Chem. 2000, 2, 732–735.
   PubMed Web of Science ®Google Scholar
• (a) Shaabani, A.; Bazgir, A.; Bijanzadeh, H. R. Mol. Divers. 2004, 8, 141–145; (b) Shaabani, A.; Bazgir, A. Tetrahedron Lett. 2004, 45, 2575–2577; (c) Abelman, M. M.; Smith, S. C.; James, D. R. Tetrahedron Lett. 2003, 44, 4559–4562; (d) Zhu, Y.; Pan, Y.; Huang, S. Heterocycles 2005, 65, 133–142.
   PubMed Web of Science ®Google Scholar
• Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
   Google Scholar
• (a) Kaminsky, J. J.; Doweyko, A. M. J. Med. Chem. 1997, 40, 427–436; (b) Katsura, Y.; Nishino, S.; Inoue, Y.; Tomoi, M.; Takasugi, H. Chem. Pharm. Bull. 1992, 40, 371–380; (c) Kaminsky, J. J.; Puchalski, C.; Solomon, D. M.; Rizvi, R. K.; Conn, D. J.; Elliot, A. J.; Lovey, R. G.; Guzik, H.; Chui, P. J. S.; Long, J. F. J. Med. Chem. 1989, 32, 1686–1700.
   PubMed Web of Science ®Google Scholar
• Okubo, T.; Yoshikawa, R.; Chaki, S.; Okuyama, S.; Nakazato, A. Bioorg. Med. Chem. 2004, 12, 423–438.
   PubMed Web of Science ®Google Scholar
• Cheung, M. P. A.; Harris, M.; Hasegawa, S.; Kano, I. K.; Nishigaki, N.; Sato, H.; Veal, J. M.; Washio, Y.; West, R. I. WO Patent 2002044156, 2002.
   Google Scholar
• Goodacre, S. C.; Street, L. J.; Hallett, D. J.; Crawforth, J. M.; Kelly, S.; Owens, A. P.; Blackaby, W. P.; Lewis, R. T.; Stanley, J.; Smith, A. J.; Ferris, P.; Sohal, B.; Cook, S. M.; Pike, A.; Brown, N.; Wafford, K. A.; Marshall, G.; Castro, J. L.; Atack, J. R. J. Med. Chem. 2006, 49, 35–38.
   PubMed Web of Science ®Google Scholar
• (a) Guzeldemirci, N. U.; Kucukbasmaci, O. Eur. J. Med. Chem. 2010, 45, 63–68; (b) Gadad, A. K.; Mahajanshetti, C. S.; Nimbalkar, S.; Raichurkar, A. Eur. J. Med. Chem. 2000, 35, 853–857.
   PubMed Web of Science ®Google Scholar
• (a) Abdel-Hafez, A. A. M. Arch. Pharmacol. Res. 2007, 30, 678–684; (b) Whitten, J. P.; Schwaebe, M. WO Patent 2008060693, 2008.
   PubMed Web of Science ®Google Scholar
• (a) Robert, J. F.; Boukraa, S.; Panouse, J. J.; Loppinet, V.; Chaumont, J. P. Eur. J. Med. Chem. 1990, 25, 731–736; (b) Amarouch, H.; Loiseau, P. R.; Bacha, C.; Caujolle, R.; Payard, M.; Loiseau, P. M.; Bories, C.; Gayral, P. Eur. J. Med. Chem. 1987, 22, 463–466.
   Web of Science ®Google Scholar
• Zanatta, N.; Amaral, S. S.; Esteves-Souza, A.; Echevarria, A.; Brondani, P. B.; Flores, D. C.; Bonacorso, H. G.; Flores, A. F. C.; Martins, M. A. P. Synthesis 2006, 14, 2305–2315.
   Web of Science ®Google Scholar
• (a) Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Bossa, R.; Fraccati, A.; Galatulas, I. J. Med. Chem. 1996, 39, 2852–2855; (b) Andreani, A.; Rambaldi, M.; Locatelli, A.; Bossa, R.; Fraccari, A.; Galatulas, I. Pharm. Acta Helv. 1993, 68, 21–24; (c) Andreani, A.; Rambaldi, M.; Andreani, F.; Bossa, R.; Galatulas, I. Eur. J. Med. Chem. 1988, 23, 385–389.
   Web of Science ®Google Scholar
• Martin, M. W.; Newcomb, J.; Nunes, J. J.; Boucher, C.; Chai, L.; Epstein, L. F.; Faust, T.; Flores, S.; Gallant, P.; Gore, A.; Gu, Y.; Hsieh, F.; Huang, X.; Kim, J. L.; Middleton, S.; Morgenstern, K.; Oliveira-dos-Santos, A.; Patel, V. F.; Powers, D.; Rose, P.; Tudor, Y.; Turci, S. M.; Welcher, A. A.; Zack, D.; Zhao, H. L.; Zhu, L.; Zhu, X.; Ghiron, C.; Ermann, M.; Johnston, D.; Saluste, C. G. J. Med. Chem. 2008, 51, 1637–1648.
   PubMed Web of Science ®Google Scholar
• (a) Sanaeishoar, T. Appl. Catal. A. 2014, 470, 56–62; (b) Che, C.; Xiang, J.; Wang, G. X.; Fathi, R.; Quan, J. M.; Yang, Z. J. Comb. Chem. 2007, 9, 982–989 (c) Mironov, M. A.; Tokareva, M. I.; Ivantsova, M. N.; Mokruskin, V. S. Russ. Chem. Bull. Int. Ed. 2006, 55, 1835–1839.
   Web of Science ®Google Scholar
• Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40, 7665–7669.
   Web of Science ®Google Scholar
• Chen, J. J.; Golebiowski, A.; Mc Clenaghan, J.; Klopfenstein, S. R.; West, L. Tetrahedron Lett. 2001, 42, 2269–2271.
   Web of Science ®Google Scholar
• Ireland, S. M.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2003, 44, 4369–4371.
   Web of Science ®Google Scholar
• Rousseau, A. L.; Matlaba, P.; Parkinson, C. J. Tetrahedron Lett. 2007, 48, 4079–4082.
   Web of Science ®Google Scholar
• Khan, A. T.; Basha, R. S.; Lal, M. Tetrahedron Lett. 2012, 53, 2211–2217.
   Web of Science ®Google Scholar
• Shaabani, A.; Soleimani, E.; Maleki, A. Tetrahedron Lett. 2006, 47, 3031–3034.
   Web of Science ®Google Scholar
• (a) Nordqvist, A.; Nilsson, M. T.; Lagerlund, O.; Muthas, D.; Gising, J.; Yahiaoui, S.; Odell, L. R.; Srinivasa, B. R.; Larhed, M.; Mowbray, S. L. Med. Chem. Commun. 2012, 3, 620–626; (b) Chernyak, N.; Gevorgyan, V. Angew. Chem. Int. Ed. 2010, 49, 2743–2746; (c) Bakherad, M.; Isfahani, H. N.; Keivanloo, A.; Doostmohammadi, N. Tetrahedron Lett. 2008, 49, 3819–3822; (d) Yadav, J. S.; Reddy, B. V. S.; Rao, Y. G.; Srinivas, M.; Narsaiah, A. V. Tetrahedron Lett. 2007, 48, 7717–7720; (e) DiMauro, E. F.; Kennedy, J. M. J. Org. Chem. 2007, 72, 1013–1016; (f) Blackburn, C. Tetrahedron Lett. 1998, 39, 5469–5472; (g) Bienayme, H.; Bouzid, K. Angew. Chem. Int. Ed. 1998, 37, 2234–2237.
   Web of Science ®Google Scholar
• Adib, M.; Mahdavi, M.; Noghani, M. A.; Mirzaei, P. Tetrahedron Lett. 2007, 48, 7263–7265.
   Web of Science ®Google Scholar
• (a) Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661–663; (b) Blackburn, C. Tetrahedron Lett. 1998, 39, 5469–5472; (c) Bienayme, H.; Bouzid, K. Angew. Chem. Int. Ed. 1998, 37, 2352–2255.
   Web of Science ®Google Scholar
• Sahu, P. K.; Lal, J.; Thavaselvam, D.; Agarwal, D. D. Med Chem. Res. 2012, 21, 3826–3834.
   Web of Science ®Google Scholar
• (a) Dam, B.; Nandi, S.; Pal, A. K. Tetrahedron Lett. 2014, 55, 5236–5240; (b) Dam, B.; Saha, M.; Pal, A. K. Catal. Lett. 2015, 145, 1808–1816.
   Web of Science ®Google Scholar
• Das, V. K.; Borah, M.; Thakur, A. J. J. Org. Chem. 2013, 78, 3361–3366.
   PubMed Web of Science ®Google Scholar
• (a) Martins, M. A. P.; Frizzo, C. P.; Moreira, N. D.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140–4182; (b) Walsh, P. J.; Li, H.; de Parrodi, C. A. Chem. Rev. 2007, 107, 2503–2545; (c) Tanaka, K. Solvent Free Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2009.
   PubMed Web of Science ®Google Scholar
• Hui, C.; Shen, C.; Yang, T.; Bao, L.; Tian, J.; Ding, H.; Li, C.; Gao, H. J. J. Phys. Chem. C. 2008, 112, 11336–11339.
   Web of Science ®Google Scholar
• Liu, J.; Lei, M.; Hu, L. Green Chem. 2012, 14, 840–846.
   Web of Science ®Google Scholar
• Shaterian, H. R.; Fahimi, N.; Azizi, K. Res Chem Intermed. 2014, 40, 1879–1898.
   Web of Science ®Google Scholar
• Amoozadeh, A.; Rahmani, S. J. Mol. Catal. A: Chem. 2015, 396, 96–107.
   Web of Science ®Google Scholar