Synthesis of Some Selectively N-Protected (1S,2S)-p-Nitrophenylserinol–Based Diamino-1,3-dioxanes and Tripodands

References

• (a) Ehrlich, J.; Bartz, Q. R.; Smith, R. M.; Josylyn, D. A.; Burkholder, P. R. Science 1947, 106, 417; (b) Smadel, J. E.; Jackson, E. B. Science 1947, 106, 418–419; (c) Rebstock, M. C.; Crooks, H. M.; Controulis, J.; Bartz, R. Q. J. Am. Chem. Soc. 1949, 71, 2458–2462; (d) Controulis, J.; Rebstock, M. C.; Crooks, H. M. J. Am. Chem. Soc. 1949, 71, 2463–2468; (e) Long, M. L.; Troutman, H. D. J. Am. Chem. Soc. 1949, 71, 2469–2472; (f) Long, M. L.; Troutman, H. D. J. Am. Chem. Soc. 1949, 71, 2473–2475.
   PubMed Web of Science ®Google Scholar
• For reviews referring to the title topic, see (a) Darabantu, M. Curr. Org. Synth. 2010, 7, 235–275; (b) Darabantu, M. Curr. Org. Synth. 2010, 7, 120–152; (c) Darabantu, M.; Mager, S.; Plé, G.; Puscas, C. Heterocycles 1995, 41, 2327–2356, and the literature cited therein.
   Web of Science ®Google Scholar
• (a) Moore, A. C. 1-Nitrophenyl-2-acylamino-1,3-propanediol acetals. U.S. Patent 2,568,555, September 18, 1951; cf. Chem. Abstr. 1952, 46, P3574d; (b) Nagawa, M. Yakugaku Zasshi 1960, 80, 761–766; cf. Chem. Abstr. 1960, 54, 24746i; (c) Contreras, C. E. Anales Fac. Quim. Univ. Chile 1963, 15, 106–112; cf. Chem. Abstr. 1965, 63, 4282h.
   Google Scholar
• (a) Eliel, E. L.; Wilen, H. S. Stereochemistry of the Organic Compounds; John Wiley & Sons: New York, 1994; pp. 1191, 696, 697, 21, 466; (b) Anteunis, M. J. O.; Tavernier, D.; Borremans, F. Heterocycles 1976, 4, 293–371; (c) Darabantu, M.; Mager, S.; Puscas, C.; Bogdan, M.; Plé, G.; Cotora, E.; Kovacs, D. Rev. Roum. Chim. 1995, 40, 453–461.
   Google Scholar
• For example, (a) Meeskens, A. J. F. Synthesis 1981, 7, 501–522; (b) Gabler, W.; Hauptmann, S. Z. Naturforsch 1968, 23b, 111–112; (c) Krauz, B. O.; Remuzov, A. L. Zh. Org. Khim. 1979, 15, 1282–1289; (d) Pihlaja, K.; Hellman, J.; Mattinen, J.; Göndös, G.; Wittman, G.; Gera, L.; Bartók, M.; Pelczer, I.; Dombi, G. Acta. Chem. Scand. Ser. B42 1988, 42, 601–604; (e) Sørbye, K.; Carlssen, P. H. J. Synth. Commun. 1997, 27, 2813–2816; (f) Juaristi, E.; Diaz, F.; Cuéllar, G.; Jiménez-Vázquez, H. A. J. Org. Chem. 1997, 62, 4029–4035; (g) Bi, L.; Zhao, M.; Wang, C.; Peng, S. Eur. J. Org. Chem. 2000, 14, 2669–2676; (h) Ooi, H.; Ishibashi, N.; Iwabuchi, Y.; Ishihara, J.; Hatakeyama, S. A. J. Org. Chem. 2004, 69, 7765–7768.
   Web of Science ®Google Scholar
• Meslard, J. C.; Subira, F.; Vairon, J. P.; Guy, A.; Garreau, R. Bull. Soc. Chim. Fr. 1985, 1, 84–89.
   Google Scholar
• (a) Darabantu, M.; Mager, S.; Puscas, C.; Bogdan, M.; Cotora, E.; Plé, G.; Bratu, I. Rev. Roum. Chim. 1994, 39, 955–965; (b) Darabantu, M.; Plé, G.; Mager, S.; Puscas, C.; Cotora, E. Tetrahedron 1997, 53, 1909–1922; (c) Darabantu, M.; Maiereanu, C.; Plé, G.; Berghian, C.; Condamine, E.; Ramondenc, Y. Heterocycl. Commun. 2001, 7, 593–598; (d) Fazekas, M.; Pintea, M.; Lameiras, P.; Lesur, A.; Berghian, C.; Silaghi-Dumitrescu, I.; Plé, N.; Darabantu, M. Eur. J. Org. Chem. 2008, 14, 2473–2494.
   Web of Science ®Google Scholar
• Nagawa, M. Ann. Rept. Takamine Lab. 1955, 7, 1–3; cf. Chem. Abstr. 1956, 50, 14764c.
   Google Scholar
• (a) Weinges, K.; Blackholm, H. Chem. Ber. 1973, 106, 2291–2297; (b) Weinges, K.; Klotz, K.-P.; Droste, H. Chem. Ber. 1980, 113, 710–721; (c) Nordin, I. C.; Thomas, J. A. Tetrahedron Lett. 1984, 25, 5723–5724; (d) Chênevert, R.; Voyer, N. Synthesis 1985, 981–982.
   Google Scholar
• For example, (a) Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953–4959; (b) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970–992; (c) Enders, D.; Breuer, K.; Runsink, J.; Teles, H. Helv. Chim. Acta 1996, 79, 1899–1902; (d) Mino, T.; Saitoh, M.; Yamashita, M. J. Org. Chem. 1997, 62, 3981–3983; (e) Strotmann, M.; Butenschön, H. Eur. J. Org. Chem. 2000, 12, 2273–2284.
   Web of Science ®Google Scholar
• (a) Chakraborti, A. K.; Chankeshwara, S. V. Org. Biomol. Chem. 2006, 4, 2769–2771; (b) Sarkar, A.; Roy, S. R.; Parikh, N.; Chakraborti, A. K. J. Org. Chem. 2011, 76, 7132–7140.
   PubMed Web of Science ®Google Scholar
• (a) Rivara, S.; Lodola, A.; Mor, M.; Bedini, A.; Spadoni, G.; Lucini, V.; Pannacci, M.; Fraschini, F.; Scaglione, F.; Sanchez, R. O.; Gobbi, G.; Tarzia, G. J. Med. Chem. 2007, 26, 6618–6626; (b) Rivara, S.; Vacondio, F.; Fioni, A.; Silva, C.; Carmi, C.; Mor, M.; Lucini, V.; Pannacci, M.; Caronno, A.; Scaglione, F.; Gobbi, G.; Spadoni, G.; Bedini, A.; Orlando, P.; Lucarini, S.; Tarzia, G. Chem Med Chem 2009, 10, 1746–1755; (c) Righi, M.; Bedini, A.; Piersanti, G.; Romagnoli, F.; Spadoni, G. J. Org. Chem. 2011, 76, 704–707; (d) D’Anello, M.; Re, M. Process for the preparation of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides, U.S. Patent 2012/0220771 A1, August 30, 2012; (e) D’Anello, M.; Re, M. Process for the preparation of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides, U.S. Patent 8,592,583 B2, November 26, 2013.
   Web of Science ®Google Scholar
• (a) Nagawa, M. Takamine Kenkyusho Nempo 1958, 10, 11–19; cf. Chem. Abstr. 1961, 55, 3502i; (b) for (l, rac)-IB see also Ueyanagi, J. J. Pharm. Soc. Japan 1951, 71, 1398–1403; cf. Chem. Abstr. 1952, 46, 8051d.
   Google Scholar
• Ramesh, S.; Williams, L. L.; Gupta, R. B.; Lin, L.-T. W. 1,3,5-Triazines compounds substituted with acetal and/or cyclized acetal-based groups. U.S. Patent 5,672,703, September 30, 1997.
   Google Scholar
• Atwood, J. L.; Steed, J. W. (Eds.). Encyclopedia of Supramolecular Chemistry, vol. 2, Marcel Dekker: New York, 2004; pp. 1106–1119.
   Google Scholar
• (a) Katritzky, A. R.; Ghiviriga, I.; Oniciu, D.; Barkock, A. J. Chem. Soc. Perkin Trans. 2 1995, 785–792; (b) Katritzky, A. R.; Ghiviriga, I.; Steel, P. G.; Oniciu, D. C. J. Chem. Soc. Perkin Trans. 2 1996, 443–447; (c) Ghiviriga, I.; Oniciu, D. C. Chem. Commun. 2002, 22, 2718–2719.
   Google Scholar
• (a) Gutowski, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228–1234; (b) Friebolin, H. Basic One- and Two-Dimensional NMR Spectroscopy; VCH Verlagsgesellschaft: Weinheim, Germany, 1991: pp. 93, 263–291.
   Web of Science ®Google Scholar
• (a) Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512–523; (b) Moreno, X. K.; Simanek, E. E. Macromolecules 2008, 41, 4108–4114.
   Web of Science ®Google Scholar
• Stewart, W. E.; Siddall, T. H. T. H. Chem. Rev. 1970, 70, 517–551.
   Web of Science ®Google Scholar