Water-mediated synthesis of disubstituted 5-aminopyrimidines from vinyl azides under microwave irradiation

References

• Abe Brown, R.C.D. J. Chem. Soc. Perkin Trans., 1998, 1, 3293. doi: 10.1039/a805801f
   Google Scholar
• Noriyuki, K.; Hitoshi, M.; Shionogi & Co. Ltd., Japan PCT Int. Appl. WO 03, 47, 564, 2002; Noriyuki, K.; Hitoshi, M.; Chem. Abstr., 2003, 139, 36532c.
   Google Scholar
• Jani, M.K.; Shah, B.R.; Undavia, N.K.; Trivedi, P.B. Chem. Abstr., 1994, 121, 35513p.
   Google Scholar
• Safonova, T.V.; Keremov, A.F.; Ershova, Y.A. Khim. Farm. Zn., 1998, 32, 11 (Eng); Safonova, T.V.; Keremov, A.F.; Ershova, Y.A. Chem. Abstr., 1999, 131, 18975e.
   Google Scholar
• Jean-Damien, C.; David, B.; Ronald, K.; Julian, G.; Pan, Li; Robert, D. Vertex Pharmaceuticals Incorporated, USA; PCT Int. Appl. WO 02 22, 608, 2002; Jean-Damien, C.; David, B.; Ronald, K.; Julian, G.; Pan, Li; Robert, D. Chem. Abstr., 2002, 136, 247584x.
   Google Scholar
• Nakaguti, O.; Shimazaki, N.; Shimazaki, M.; Nakatuka, M. Eur. Pat. Appl., 1986 , 168, 005; Nakaguti, O.; Shimazaki, N.; Shimazaki, M.; Nakatuka, M. Chem. Abstr., 1986, 105, 191118p.
   Google Scholar
• Papesh, V.; Schroeder, E.F. US. Pat 2714559, 1956; Papesh, V.; Schroeder, E.F. Chem. Abstr., 1956, 50, 11370.
   Google Scholar
• Tokutake, N. Brit. Pat.146836B, 1977; Tokutake, N. Chem. Abstr., 1977, 87, 102370.
   Google Scholar
• Kurono, M. JP, 62, 267, 272, 1987; Kurono, M. Chem. Abstr., 1988, 109, 37382t.
   Google Scholar
• Pershin, N.G.; Sherbakova, L.I.; Sakolova, V.N. Pharmacol. Taksiko., 1972, 35, 466.
   Google Scholar
• Metolcsy, G. World Rev. Pest Contr., 1971, 10, 50.
   Web of Science ®Google Scholar
• Regnier, G.L.; Canevar, R.J.; Douarec, L.; Halstop, S.; Daussy, J.; J. Med. Chem., 1972, 15, 295. doi: 10.1021/jm00273a600
   PubMed Web of Science ®Google Scholar
• (a) Zapol’kii, V.A.; Namyslo, J.C.; Altug, C.; Gjikaj, M.; Kaufmann, D.E. Synthesis, 2008, 304. (b) Kaname, T.; Masaaki, T.; Yukitoshi, M.; Kuniyoshi, O.; Katsuyuki, I.; Hikari, M.; Tomoji, A. J. Heterocycl. Chem., 1987, 24, 1003. (c) Masaaki, T.; Yukitoshi, M.; Hikari, M.; Kaname, T. Chem. Pharm. Bull., 1985, 33, 2129. (d) Khanzhin, N. U.S. Patent 7, 066, 612, 2007; Khanzhin, N. Chem. Abstr., 2007, 146, 337905; (e) Davey, D.D. EP Patent 1, 429,149, 1991; Davey, D.D. Chem. Abstr., 1991, 115, 183357.
   Web of Science ®Google Scholar
• (a) Hu, M.; Wu, J.; Zhang, Y.; Qiu, F.; Yu, Y. Tetrahedron, 2011, 67, 2676. (b) Hu, B.; DiMagno, S. Org. Biomol. Chem., 2015, 13, 3844. doi: 10.1016/j.tet.2011.01.062
   Web of Science ®Google Scholar
• (a) Shao, Z.; Pan, Q.; Chen, J.; Yu, Y.; Zhang, G. Tetrahedron, 2012, 68, 6565. (b) Ni, H.; Zhang, G.; Yu, Y. Current Org. Chem., 2015, 19, 776. doi: 10.1016/j.tet.2012.05.057
   Web of Science ®Google Scholar
• (a) Guo, S.; Chen, B.; Zhao, D.; Chen, W.; Zhang, G. Adv. Synth. Catal., 2016, 358, 3010. (b) Zhang, G.; Chen, B.; Guo, X.; Guo, S.; Yu, Y. Adv. Synth. Catal., 2015, 357, 1065. (c) Chen, B.; Guo, S.; Guo, X.; Zhang, G.; Yu, Y. Org. Lett., 2015, 17, 4698. (d) Guo, S.; Chen, B.; Guo, X.; Zhang, G.; Yu, Y. Tetrahedron, 2015, 71, 9371–9375. (e) Chen, B.; Ni, H.; Guo, X.; Zhang, G.; Yu, Y. RSC Adv., 2014, 4, 44462. (f) Zhang, G.; Ni, H.; Chen, W.; Shao, J.; Liu, H.; Chen, B.; Yu, Y. Org. Lett., 2013, 15, 5967. (g) Zhang, Y.; Liu, S.; Yu, Hu, M. Zhang, G.; Yu, Y. Tetrahedron, 2013, 69, 2070. doi: 10.1002/adsc.201600423
   Web of Science ®Google Scholar
• (a) Riadi, Y.; Geesi, M. Chem. Pap., 2017, 1. doi:10.1007/s11696-017-0325-2. (b) Riadi, Y.; Massip, S.; Leger, J. M.; Jarry, C.; Lazar, S.; Guillaumet, G. Tetrahedron, 2012, 68, 5018. (c) Dehbi, O.; Tikad, A.; Bourg, S.; Bonnet, P.; Lozach, O.; Meijer, L.; Aadil, M.; Akssira, M.; Guillaumet, G.; Routier, S. Eur. J. Med. Chem. 2014, 80, 352. (c) Routier, S.; Guillaumet, G.; Tikad, A.; Dehbi, O. Preparation of Pyrido[3,2-d]pyrimidine Derivatives as Inhibitors of CDK1, DYRK1A, CDK5 and/or GSK3 kinases, WO 2011135259, Chem. Abstract 155:637809, 2011.
   Web of Science ®Google Scholar
• (a) Riadi, Y.; Mamouni, R.; Azzalou, R.; El Haddad, M.; Routier, S.; Guillaumet, G.; Lazar, S. Tetrahedron Lett., 2011, 52, 3492. (b) Riadi, Y.; Mamouni, R.; Routier, S.; Guillaumet, G.; Lazar, S. Environ. Chem. Lett., 2014, 12, 523. (c) Riadi, Y.; Geesi, M.; Dehbi, O.; Bakht, M.A.; Alshammari, M.; Viaud-Massuarde, M.-C. Green Chem. Lett. Rev., 2017, 10, 101. doi: 10.1016/j.tetlet.2011.04.121
   Web of Science ®Google Scholar
• (a) Knittel, D.; Hemetsberger, H.; Weidmann, H. Monatsh. Chem., 1970,101, 157. (b) Gilchrist, T. L.; Mendonca, R. ARKIVOC, 2000, 769. (c) Patonay, T.; Jekȍ, J.; Rimàn, E. Synth. Commun., 2002, 32, 2403. doi: 10.1007/BF00907535
   Web of Science ®Google Scholar