Oxidative Additions with 1,4-Dihydropyridines: A One-Pot Synthesis of 3,4,4a,5,8,8a-Hexahydro-2H-pyrido[3,2-b][1,4]oxazine Derivatives

REFERENCES

• Bourlot, A.-S., Sanchez, I., Dureng, G., Guillaument, G., Massingham, R., Monteil, A., Winslow, E., Pujol, M. D., and Merour, J.-Y., 1998. New substituted 1,4-benzoxazine derivatives with potential intracellular calcium activity, J. Med. Chem. 41 (1998), pp. 3142–3158.
   PubMed Web of Science ®Google Scholar
• Kuroita, T., Marubayashi, N., Sano, M., Kanzaki, K., Inaba, K., and Kawakita, T., 1996. Benzoxazine, II: Synthesis, conformational analysis, and structure-activity relationships of 3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide derivatives as potent and long-acting serotonin-3 (5-HT3) receptor antagonists, Chem. Pharm. Bull. 44 (1996), pp. 2051–2060.
   PubMed Web of Science ®Google Scholar
• Matsumoto, Y., Tsuzuki, R., Matsuhisa, A., Masuda, N., Yamagiwa, Y., Yanagisawa, I., Shibanuma, T., and Nohira, H., 1999. Novel potassium channel activators, II: synthesis and pharmacological evaluation of 3,4-dihydro-2H-1,4-benzoxazine derivatives: Modificaiton of the aromatic part, Chem. Pharm. Bull. 47 (1999), pp. 971–979.
   PubMed Web of Science ®Google Scholar
• Buckman, B. O., Mohan, R., Koovakkat, S., Liang, A., Trinh, L., and Morrissey, M. M., 1998. Design, synthesis, and biological activity of novel purine and bicyclic pyrimidine factor Xa inhibitors, Bioorg. Med. Chem. Lett. 8 (1998), pp. 2235–2240.
   PubMed Web of Science ®Google Scholar
• Breznik, M., Hrast, V., Mrcina, A., and Kikelj, D., 1999. Stereoselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine acids, -carboxylates, and -carboxamides, Tetrahedron: Asymmetry 10 (1999), pp. 153–167.
   Google Scholar
• Kourounakis, A. P., Charitos, C., Rekka, A. A., and Kourounakis, P. N., 2008. Lipid-lowering (hetero) aromatic tetrahydro-1,4-oxazine derivatives with antioxidant and squalene synthase inhibitory activity, J. Med. Chem. 51 (2008), pp. 5861–5865.
   PubMed Web of Science ®Google Scholar
• Lepifre, F., Buon, C., and Bouyssou, P.Coudert, G., , 2000. Synthesis of 4H-pyrido[3,2-b][1,4] oxazines via palladium-catalysed reactions, Heterocycl. Commun. 6 (2000), pp. 397–402.
   Web of Science ®Google Scholar
• Arrault, A., Touzeau, F., Guillaumet, G., Leger, J.-M., Jarry, C., and Merour, J.-Y., 2002. Synthesis of functionalised pyrido[4,3-b][1,4]oxazine and imidazo[1,2-a]pyridine derivatives, Tetrahedron 58 (2002), pp. 8145–8152.
   Web of Science ®Google Scholar
• Henry, N., Guillaumet, G., and Pujol, M. D., 2004. The first enantioselective synthesis of 4-acetyl-3(R)- and 3(S)-(hydroxymethyl)-3,4-dihydro-2H-pyrido[3,2-b]oxazine, Tetrahedron Lett. 45 (2004), pp. 1465–1468.
   Web of Science ®Google Scholar
• Takeda, H., and Hisamichi, K., 1983. Studies on pyridinol derivatives, X: Synthesis and pharmacological activity of 2H-pyrido[3,2-b]-1,4-oxazin derivatives, Yakugaku Zasshi 103 (1983), pp. 1247–1256.
   PubMedGoogle Scholar
• Stout, D. M., 1982. Recent advances in the chemistry of dihydropyridines, Chem. Rev. 82 (1982), pp. 223–243.
   Web of Science ®Google Scholar
• Lavilla, R., Coll, O., Nicolàs, M., and Bosch, J., 1998. Iodocyclization of 1,4-dihydropyridines, Tetrahedron Lett. 39 (1998), pp. 5089–5092.
   Web of Science ®Google Scholar
• Lavilla, R., Coll, O., Kumar, R., and Bosch, J., 1998. Electrophilic oxidative additions upon 1,4-dihydropyridines, J. Org. Chem. 63 (1998), pp. 2728–2730.
   PubMed Web of Science ®Google Scholar
• Warren, B. K., and Knaus, E. E., 1981. Some reactions of 1,4-dihydropyridines with organic azides: Synthesis of 2,7-diazabicyclo [4.1.0] hept-3-enes with analgesic and antiprotozoal activity, J. Med. Chem. 24 (1981).
   PubMed Web of Science ®Google Scholar
• Brewster, M. E., Simay, A., Czako, K., Winwood, D., Farag, H., and Bodor, N., 1989. Reactivity of biologically important reduced pyridines: Effect of substitution on ferricyanide-mediated oxidation rates of various 1,4-dihydropyridines, J. Org. Chem. 54 (1989), pp. 3721–3726.
   Web of Science ®Google Scholar
• De Sousa, S. E., and Brien, P. O., 1997. Aziridinium ions from phenylglycinol—A new approach to the synthesis of chiral diamines, Tetrahedron Lett. 38 (1997), pp. 4885–4888.
   Web of Science ®Google Scholar
• Lavilla, R., Kumar, R., Coll, O., Masdeu, C., and Bosch, J., 1998. Vicinal diamination of 1,4-dihydropyridines, Chem. Commun. (1998), pp. 2715–2716.
   Web of Science ®Google Scholar