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

Pure and Applied Chemistry

Volumn 84, Issue 3, 2012, Pages 707-719

  Robert McElroy, C ^a   Aricò, Fabio ^a   Benetollo, Franco ^b   Tundo, Pietro ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b CNR   (Italy)

Author keywords

Cyclic carbamates; Cyclizations; Dialkyl carbonate; Green chemistry; Heterocyclic chemistry

Indexed keywords

1 ,3-DIOLS; CYCLIC CARBAMATES; CYCLIZATION REACTIONS; CYCLIZATIONS; DIALKYL CARBONATES; DICARBONATE; GOOD YIELD; GREEN CHEMISTRY; INTERMOLECULAR REACTIONS; INTRAMOLECULAR CYCLIZATIONS; LEAVING GROUPS; ONE-POT REACTION; PRIMARY AMINES; TIME SPAN;

CYCLIZATION; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

EID: 84858111765     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-11-07-18     Document Type: Article

References (54)

1. M. Liu, Y. Hashi, Y. Song, J. Lin. J. Chromatogr., A 1097, 183 (2005).
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).
4. P. Adams, F. A. Baron. Chem. Rev. 65, 567 (1965).
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).
7. G. Wang, J. Ella-Menye, V. Sharma. Bioorg. Med. Chem. Lett. 16, 2177 (2006).
8. W. J. Close. J. Am. Chem. Soc. 73, 95 (1951).
9. L. Huang, L. S. Brinen, J. Ellman. Bioorg. Med. Chem. 11, 21 (2003).
10. D. Ondre, J. Wolfling, Z. Ivanyi, G. Schneider, T. Istvan, M. Szecsi, J. Julesz. Steroids 73, 1375 (2008).
11. A. W. Dox, L. Yoder. J. Am. Chem. Soc. 45, 723 (1923).
12. M. Fujiwara, A. Baba, H. Matsuda. J. Heterocycl. Chem. 26, 1659 (1989).
13. I. Shibata, K. Nakamura, A. Baba, H. Matsuda. Bull. Chem. Soc. Jpn. 62, 853 (1989).
14. A. Baba, I. Shibata, M. Fujiwara, H. Matsuda. Tetrahedron Lett. 26, 5167 (1985).
15. G. T. Rice, M. C. White. J. Am. Chem. Soc. 131, 11707 (2009).
16. F. Nahra, F. Liron, G. Prestat, C. Mealli, A. Messaoudi, G. Poli. Chem.-Eur. J. 15, 11078 (2009).
17. S. Mangelinckx, Y. Nural, H. A. Dondas, B. Denolf, R. Sillanpaa, N. De Kimpe. Tetrahedron 66, 4115 (2010).
18. S. G. Davies, A. C. Garner, P. M. Robert, A. D. Smith, M. J. Sweet, J. E. Thomson. Org. Biomol. Chem. 4, 2753 (2006).
19. M. Park, J. Lee. Arch. Pharmacol. Res. 16, 158 (1993).
20. X. Li, R. Wang, Y. Wang, H. Chen, Z. Li, C. Ba, J. Zhang. Tetrahedron 64, 9911 (2008).
21. Ullman Encyclopedia: Industrial Organic Chemicals: Starting Materials and Intermediates. Vol. 2, p. 1045, Wiley-VCH, New York (1999).
22. L. Cotarca, H. Eckert. Phosgenations: A Handbook. p. 589, Wiley-VCH (2004).
23. J. Jung, M. A. Avery. Tetrahedron Lett. 47, 7969 (2006).
24. Y. Kayaki, N. Mori, T. Ikariya. Tetrahedron Lett. 50, 6491 (2009).
25. J. Paz, C. Pèrez-Balado, B. Iglesias, L. Munoz. J. Org. Chem. 75, 3037 (2010).
26. R. Juárez, P. Concepción, A. Corma, H. García. Chem. Commun. 46, 4181 (2010).
27. Y. J. Kim, R. S. Varma. Tetrahedron Lett. 45, 7205 (2004).
28. B. M. Bhanage, S. Fujita, Y. Ikushima, M. Arai. Green Chem. 6, 78 (2004).
29. 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).
30. S. Trifunovic, D. Dimitrijevic, G. Vasic, R. D. Vukicevic, N. Radulovic, M. Vukicevic, F. W. Heinemann. Synthesis 6, 943 (2010).
31. P. Tundo, M. Selva. Acc. Chem. Res. 35, 706 (2002).
32. M. Selva, P. Tundo. J. Org. Chem. 71, 1464 (2006).
33. H. Zhou, F. Shi, X. Tian, Q. Zhang, Y. Deng. J. Mol. Catal., A 271, 89 (2007).
34. M. Distaso, E. Quaranta. Appl. Catal., B 66, 72 (2006).
35. P. Tundo, S. Bressanello, A. Loris, G. Sathicq. Pure Appl. Chem. 77, 1719 (2005).
36. M. Distaso, E. Quaranta. J. Catal. 228, 36 (2004).
37. T. Baba, A. Kobayashi, T. Yamauchi, H. Tanaka, S. Aso, M. Inomata, Y. Kawanami. Catal. Lett. 82, 193 (2002).
38. A. E. Rosamilia, F. Aricò, P. Tundo. J. Org. Chem. 73, 1559 (2008).
39. Y. Li, X. Zhao, Y. Wang. J. Appl. Catal., A 279, 205 (2005).
40. H. S. Bevinakatti, C. P. Newman, S. Elwood, P. Tundo, F. Aricò. Cyclic Ethers. International Patent PCT/GB2008/050567, 22 January 2009.
41. R. G. Pearson. J. Am. Chem. Soc. 85, 3533 (1963).
42. M. Selva, A. Bomben, P. Tundo. J. Chem. Soc., Perkin Trans. 1 1041 (1997).
43. P. Tundo, M. Selva, A. Perosa, S. Memoli. J. Org. Chem. 67, 1071 (2002).
44. P. Tundo, M. Selva, A. Bomben. Org. Synth. 76, 640 (2004).
45. P. Tundo, C. R. McElroy, F. Aricò. Synlett 10, 1567 (2010).
46. After 3 h at 90 °C, 0.5 equiv of base, in the absence of a solvent.
47. 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 %).
48. P. Tundo, S. Bressanello, A. Loris, G. Sathicq. Pure Appl. Chem. 77, 1719 (2005).
49. G. Y. Lesher, A. R. Surrey. J. Am. Chem. Soc. 77, 636 (1955).
50. S. Porwanski, S. Menuel, X. Marsura, A. Marsura. Tetrahedron Lett. 45, 5027 (2004).
51. 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).
52. G. M. Sheldrick. "SHELXL-97", Program for the Refinement of Crystal Structures, University of Göttingen, Germany (1997).
53. L. J. Farrugia. J. Appl. Crystallogr. 32, 837 (1999).
54. L. J. Farrugia. ORTEP3 for Windows, J. Appl. Crystallogr. 30, 565 (1997).