Pure and Applied Chemistry

Pure Appl. Chem., 2012, Vol. 84, No. 3, pp. 707-719

http://dx.doi.org/10.1351/PAC-CON-11-07-18

Published online 2011-11-23

Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones*

References

• 1. M. Liu, Y. Hashi, Y. Song, J. Lin. J. Chromatogr., A 1097, 183 (2005). (http://dx.doi.org/10.1016/j.chroma.2005.10.022)
• 2. W. Tai-The, J. Huang, N. Arrington, G. M. Dill. J. Agric. Food Chem. 35, 817 (1987).
• 3. I. Vauthey, F. Valot, C. Gozzi, F. Fache, M. Lemaine. Tetrahedron Lett. 41, 6347 (2000). (http://dx.doi.org/10.1016/S0040-4039(00)01051-0)
• 4. P. Adams, F. A. Baron. Chem. Rev. 65, 567 (1965). (http://dx.doi.org/10.1021/cr60237a002)
• 5. T. W. Greene, P. G. M. Wuts. In Protective Groups in Organic Synthesis, p. 503, Wiley-VCH, Weinheim (1998).
• 6. J. Kusan, H. Keul, H. Hocker. Macromolecules 34, 389 (2001). (http://dx.doi.org/10.1021/ma000535c)
• 7. G. Wang, J. Ella-Menye, V. Sharma. Bioorg. Med. Chem. Lett. 16, 2177 (2006). (http://dx.doi.org/10.1016/j.bmcl.2006.01.072)
• 8. W. J. Close. J. Am. Chem. Soc. 73, 95 (1951). (http://dx.doi.org/10.1021/ja01145a035)
• 9. L. Huang, L. S. Brinen, J. Ellman. Bioorg. Med. Chem. 11, 21 (2003). (http://dx.doi.org/10.1016/S0968-0896(02)00427-3)
• 10. D. Ondre, J. Wolfling, Z. Ivanyi, G. Schneider, T. Istvan, M. Szecsi, J. Julesz. Steroids 73, 1375 (2008). (http://dx.doi.org/10.1016/j.steroids.2008.06.011)
• 11. A. W. Dox, L. Yoder. J. Am. Chem. Soc. 45, 723 (1923). (http://dx.doi.org/10.1021/ja01656a025)
• 12a. M. Fujiwara, A. Baba, H. Matsuda. J. Heterocycl. Chem. 26, 1659 (1989). (http://dx.doi.org/10.1002/jhet.5570260628)
• 12b. I. Shibata, K. Nakamura, A. Baba, H. Matsuda. Bull. Chem. Soc. Jpn. 62, 853 (1989). (http://dx.doi.org/10.1246/bcsj.62.853)
• 12c. A. Baba, I. Shibata, M. Fujiwara, H. Matsuda. Tetrahedron Lett. 26, 5167 (1985). (http://dx.doi.org/10.1016/S0040-4039(00)98893-2)
• 13a. G. T. Rice, M. C. White. J. Am. Chem. Soc. 131, 11707 (2009). (http://dx.doi.org/10.1021/ja9054959)
• 13b. F. Nahra, F. Liron, G. Prestat, C. Mealli, A. Messaoudi, G. Poli. Chem.—Eur. J. 15, 11078 (2009). (http://dx.doi.org/10.1002/chem.200901946)
• 13c. S. Mangelinckx, Y. Nural, H. A. Dondas, B. Denolf, R. Sillanpaa, N. De Kimpe. Tetrahedron 66, 4115 (2010). (http://dx.doi.org/10.1016/j.tet.2010.03.113)
• 14. S. G. Davies, A. C. Garner, P. M. Robert, A. D. Smith, M. J. Sweet, J. E. Thomson. Org. Biomol. Chem. 4, 2753 (2006). (http://dx.doi.org/10.1039/b604073j)
• 15a. M. Park, J. Lee. Arch. Pharmacol. Res. 16, 158 (1993). (http://dx.doi.org/10.1007/BF03036866)
• 15b. X. Li, R. Wang, Y. Wang, H. Chen, Z. Li, C. Ba, J. Zhang. Tetrahedron 64, 9911 (2008). (http://dx.doi.org/10.1016/j.tet.2008.08.002)
• 16. Ullman Encyclopedia: Industrial Organic Chemicals: Starting Materials and Intermediates, Vol. 2, p. 1045, Wiley-VCH, New York (1999).
• 17. L. Cotarca, H. Eckert. Phosgenations: A Handbook, p. 589, Wiley-VCH (2004).
• 18. J. Jung, M. A. Avery. Tetrahedron Lett. 47, 7969 (2006). (http://dx.doi.org/10.1016/j.tetlet.2006.08.111)
• 19. Y. Kayaki, N. Mori, T. Ikariya. Tetrahedron Lett. 50, 6491 (2009). (http://dx.doi.org/10.1016/j.tetlet.2009.09.015)
• 20. J. Paz, C. Pèrez-Balado, B. Iglesias, L. Munoz. J. Org. Chem. 75, 3037 (2010). (http://dx.doi.org/10.1021/jo100268n)
• 21. R. Juárez, P. Concepción, A. Corma, H. García. Chem. Commun. 46, 4181 (2010). (http://dx.doi.org/10.1039/c001955k)
• 22a. Y. J. Kim, R. S. Varma. Tetrahedron Lett. 45, 7205 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.08.042)
• 22b. B. M. Bhanage, S. Fujita, Y. Ikushima, M. Arai. Green Chem. 6, 78 (2004). (http://dx.doi.org/10.1039/b310115k)
• 23. J. X. Qiao, C. Chang, D. L. Cheney, P. E. Morin, G. E. Wang, S. R. King, T. C. Wang, A. R. Rendina, J. M. Luettgen, R. M. Knabb, R. R. Wexler, P. Y. S. Lam. Bioorg. Med. Chem. Lett. 17, 4419 (2007). (http://dx.doi.org/10.1016/j.bmcl.2007.06.029)
• 24. S. Trifunovic, D. Dimitrijevic, G. Vasic, R. D. Vukicevic, N. Radulovic, M. Vukicevic, F. W. Heinemann. Synthesis 6, 943 (2010).
• 25a. P. Tundo, M. Selva. Acc. Chem. Res. 35, 706 (2002). (http://dx.doi.org/10.1021/ar010076f)
• 25b. M. Selva, P. Tundo. J. Org. Chem. 71, 1464 (2006). (http://dx.doi.org/10.1021/jo0520792)
• 26a. H. Zhou, F. Shi, X. Tian, Q. Zhang, Y. Deng. J. Mol. Catal., A 271, 89 (2007).
• 26b. M. Distaso, E. Quaranta. Appl. Catal., B 66, 72 (2006).
• 27. P. Tundo, S. Bressanello, A. Loris, G. Sathicq. Pure Appl. Chem. 77, 1719 (2005). (http://dx.doi.org/10.1351/pac200577101719)
• 28a. M. Distaso, E. Quaranta. J. Catal. 228, 36 (2004). (http://dx.doi.org/10.1016/j.jcat.2004.08.004)
• 28b. T. Baba, A. Kobayashi, T. Yamauchi, H. Tanaka, S. Aso, M. Inomata, Y. Kawanami. Catal. Lett. 82, 193 (2002). (http://dx.doi.org/10.1023/A:1020566928295)
• 29. A. E. Rosamilia, F. Aricò, P. Tundo. J. Org. Chem. 73, 1559 (2008). (http://dx.doi.org/10.1021/jo701818d)
• 30. Y. Li, X. Zhao, Y. Wang. J. Appl. Catal., A 279, 205 (2005). (http://dx.doi.org/10.1016/j.apcata.2004.10.030)
• 31. H. S. Bevinakatti, C. P. Newman, S. Elwood, P. Tundo, F. Aricò. Cyclic Ethers. International Patent PCT/GB2008/050567, 22 January 2009.
• 32. R. G. Pearson. J. Am. Chem. Soc. 85, 3533 (1963). (http://dx.doi.org/10.1021/ja00905a001)
• 33a. M. Selva, A. Bomben, P. Tundo. J. Chem. Soc., Perkin Trans. 1 1041 (1997). (http://dx.doi.org/10.1039/a606684d)
• 33b. P. Tundo, M. Selva, A. Perosa, S. Memoli. J. Org. Chem. 67, 1071 (2002). (http://dx.doi.org/10.1021/jo0057699)
• 33c. P. Tundo, M. Selva, A. Bomben. Org. Synth. 76, 640 (2004).
• 34. P. Tundo, C. R. McElroy, F. Aricò. Synlett 10, 1567 (2010). (http://dx.doi.org/10.1055/s-0029-1219927)
• 35. After 3 h at 90 °C, 0.5 equiv of base, in the absence of a solvent.
• 36. Also observed was benzylamine (4 %), methyl N-benzyl carbamate 5 (27 %), 3-hydroxy-2-methylpropyl N-benzyl carbamate 6 (10 %), 1,3-dibenzylurea 7 (5 %), unreacted starting material 8 (14 %), and 2-methylpropyl-1,3-dibenzylcarbamoyl 9 (8 %).
• 37. P. Tundo, S. Bressanello, A. Loris, G. Sathicq. Pure Appl. Chem. 77, 1719 (2005). (http://dx.doi.org/10.1351/pac200577101719)
• 38. G. Y. Lesher, A. R. Surrey. J. Am. Chem. Soc. 77, 636 (1955). (http://dx.doi.org/10.1021/ja01608a032)
• 39. S. Porwanski, S. Menuel, X. Marsura, A. Marsura. Tetrahedron Lett. 45, 5027 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.05.002)
• 40. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna. J. Appl. Crystallogr. 38, 381 (2005). (http://dx.doi.org/10.1107/S002188980403225X)
• 41. G. M. Sheldrick. “SHELXL-97”, Program for the Refinement of Crystal Structures, University of Göttingen, Germany (1997).
• 42. L. J. Farrugia. J. Appl. Crystallogr. 32, 837 (1999). (http://dx.doi.org/10.1107/S0021889899006020)
• 43. L. J. Farrugia. ORTEP3 for Windows, J. Appl. Crystallogr. 30, 565 (1997). (http://dx.doi.org/10.1107/S0021889897003117)