A number of six-membered cyclic carbamates (oxazinanones) were synthesized from the reaction of a primary amine or hydrazine with a dicarbonate derivative of 1,3-diols in a one-pot reaction, in good yield, short time span, and in the absence of a solvent. The reaction proceeds in two steps: an intermolecular reaction to give a linear intermediate and an intramolecular cyclization to yield the cyclic carbamate. This is the first example of a carbonate reacting selectively and sequentially, firstly at the carbonyl center to form a linear carbamate and then as a leaving group to yield a cyclic carbamate.
References
1 10.1016/j.chroma.2005.10.022, M. Liu, Y. Hashi, Y. Song, J. Lin. J. Chromatogr., A1097, 183 (2005).Search in Google Scholar
2 W. Tai-The, J. Huang, N. Arrington, G. M. Dill. J. Agric. Food Chem.35, 817 (1987).Search in Google Scholar
3 10.1016/S0040-4039(00)01051-0, I. Vauthey, F. Valot, C. Gozzi, F. Fache, M. Lemaine. Tetrahedron Lett.41, 6347 (2000).Search in Google Scholar
4 10.1021/cr60237a002, P. Adams, F. A. Baron. Chem. Rev.65, 567 (1965).Search in Google Scholar
5 T. W. Greene, P. G. M. Wuts. In Protective Groups in Organic Synthesis, p. 503, Wiley-VCH, Weinheim (1998).10.1002/0471220574Search in Google Scholar
6 10.1021/ma000535c, J. Kusan, H. Keul, H. Hocker. Macromolecules34, 389 (2001).Search in Google Scholar
7 10.1016/j.bmcl.2006.01.072, G. Wang, J. Ella-Menye, V. Sharma. Bioorg. Med. Chem. Lett.16, 2177 (2006).Search in Google Scholar
8 10.1021/ja01145a035, W. J. Close. J. Am. Chem. Soc.73, 95 (1951).Search in Google Scholar
9 10.1016/S0968-0896(02)00427-3, L. Huang, L. S. Brinen, J. Ellman. Bioorg. Med. Chem.11, 21 (2003).Search in Google Scholar
10 10.1016/j.steroids.2008.06.011, D. Ondre, J. Wolfling, Z. Ivanyi, G. Schneider, T. Istvan, M. Szecsi, J. Julesz. Steroids73, 1375 (2008).Search in Google Scholar PubMed
11 10.1021/ja01656a025, A. W. Dox, L. Yoder. J. Am. Chem. Soc.45, 723 (1923).Search in Google Scholar
12a 10.1002/jhet.5570260628, M. Fujiwara, A. Baba, H. Matsuda. J. Heterocycl. Chem.26, 1659 (1989).Search in Google Scholar
12b 10.1246/bcsj.62.853, I. Shibata, K. Nakamura, A. Baba, H. Matsuda. Bull. Chem. Soc. Jpn.62, 853 (1989).Search in Google Scholar
12c 10.1016/S0040-4039(00)98893-2, A. Baba, I. Shibata, M. Fujiwara, H. Matsuda. Tetrahedron Lett.26, 5167 (1985).Search in Google Scholar
13a 10.1021/ja9054959, G. T. Rice, M. C. White. J. Am. Chem. Soc.131, 11707 (2009).Search in Google Scholar PubMed PubMed Central
13b 10.1002/chem.200901946, F. Nahra, F. Liron, G. Prestat, C. Mealli, A. Messaoudi, G. Poli. Chem.—Eur. J.15, 11078 (2009).Search in Google Scholar PubMed
13c 10.1016/j.tet.2010.03.113, S. Mangelinckx, Y. Nural, H. A. Dondas, B. Denolf, R. Sillanpaa, N. De Kimpe. Tetrahedron66, 4115 (2010).Search in Google Scholar
14 10.1039/b604073j, S. G. Davies, A. C. Garner, P. M. Robert, A. D. Smith, M. J. Sweet, J. E. Thomson. Org. Biomol. Chem.4, 2753 (2006).Search in Google Scholar PubMed
15a 10.1007/BF03036866, M. Park, J. Lee. Arch. Pharmacol. Res.16, 158 (1993).Search in Google Scholar
15b 10.1016/j.tet.2008.08.002, X. Li, R. Wang, Y. Wang, H. Chen, Z. Li, C. Ba, J. Zhang. Tetrahedron64, 9911 (2008).Search in Google Scholar
16 Ullman Encyclopedia: Industrial Organic Chemicals: Starting Materials and Intermediates, Vol. 2, p. 1045, Wiley-VCH, New York (1999).Search in Google Scholar
17 L. Cotarca, H. Eckert. Phosgenations: A Handbook, p. 589, Wiley-VCH (2004).Search in Google Scholar
18 10.1016/j.tetlet.2006.08.111, J. Jung, M. A. Avery. Tetrahedron Lett.47, 7969 (2006).Search in Google Scholar
19 10.1016/j.tetlet.2009.09.015, Y. Kayaki, N. Mori, T. Ikariya. Tetrahedron Lett.50, 6491 (2009).Search in Google Scholar
20 10.1021/jo100268n, J. Paz, C. Pèrez-Balado, B. Iglesias, L. Munoz. J. Org. Chem.75, 3037 (2010).Search in Google Scholar PubMed
21 10.1039/c001955k, R. Juárez, P. Concepción, A. Corma, H. García. Chem. Commun.46, 4181 (2010).Search in Google Scholar PubMed
22a 10.1016/j.tetlet.2004.08.042, Y. J. Kim, R. S. Varma. Tetrahedron Lett.45, 7205 (2004).Search in Google Scholar
22b 10.1039/b310115k, B. M. Bhanage, S. Fujita, Y. Ikushima, M. Arai. Green Chem.6, 78 (2004).Search in Google Scholar
23 10.1016/j.bmcl.2007.06.029, 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).Search in Google Scholar PubMed
24 S. Trifunovic, D. Dimitrijevic, G. Vasic, R. D. Vukicevic, N. Radulovic, M. Vukicevic, F. W. Heinemann. Synthesis6, 943 (2010).Search in Google Scholar
25a 10.1021/ar010076f, P. Tundo, M. Selva. Acc. Chem. Res.35, 706 (2002).Search in Google Scholar PubMed
25b 10.1021/jo0520792, M. Selva, P. Tundo. J. Org. Chem.71, 1464 (2006).Search in Google Scholar PubMed
26a H. Zhou, F. Shi, X. Tian, Q. Zhang, Y. Deng. J. Mol. Catal., A271, 89 (2007).10.1016/j.molcata.2007.02.017Search in Google Scholar
26b M. Distaso, E. Quaranta. Appl. Catal., B66, 72 (2006).10.1016/j.apcatb.2006.02.019Search in Google Scholar
27 10.1351/pac200577101719, P. Tundo, S. Bressanello, A. Loris, G. Sathicq. Pure Appl. Chem.77, 1719 (2005).Search in Google Scholar
28a 10.1016/j.jcat.2004.08.004, M. Distaso, E. Quaranta. J. Catal.228, 36 (2004).Search in Google Scholar
28b 10.1023/A:1020566928295, T. Baba, A. Kobayashi, T. Yamauchi, H. Tanaka, S. Aso, M. Inomata, Y. Kawanami. Catal. Lett.82, 193 (2002).Search in Google Scholar
29 10.1021/jo701818d, A. E. Rosamilia, F. Aricò, P. Tundo. J. Org. Chem.73, 1559 (2008).Search in Google Scholar PubMed
30 10.1016/j.apcata.2004.10.030, Y. Li, X. Zhao, Y. Wang. J. Appl. Catal., A279, 205 (2005).Search in Google Scholar
31 H. S. Bevinakatti, C. P. Newman, S. Elwood, P. Tundo, F. Aricò. Cyclic Ethers. International Patent PCT/GB2008/050567, 22 January 2009.Search in Google Scholar
32 10.1021/ja00905a001, R. G. Pearson. J. Am. Chem. Soc.85, 3533 (1963).Search in Google Scholar
33a 10.1039/a606684d, M. Selva, A. Bomben, P. Tundo. J. Chem. Soc., Perkin Trans. 1 1041 (1997).Search in Google Scholar
33b 10.1021/jo0057699, P. Tundo, M. Selva, A. Perosa, S. Memoli. J. Org. Chem.67, 1071 (2002).Search in Google Scholar PubMed
33c P. Tundo, M. Selva, A. Bomben. Org. Synth.76, 640 (2004).Search in Google Scholar
34 10.1055/s-0029-1219927, P. Tundo, C. R. McElroy, F. Aricò. Synlett10, 1567 (2010).Search in Google Scholar
35 After 3 h at 90 °C, 0.5 equiv of base, in the absence of a solvent.Search in Google Scholar
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 %).Search in Google Scholar
37 10.1351/pac200577101719, P. Tundo, S. Bressanello, A. Loris, G. Sathicq. Pure Appl. Chem.77, 1719 (2005).Search in Google Scholar
38 10.1021/ja01608a032, G. Y. Lesher, A. R. Surrey. J. Am. Chem. Soc.77, 636 (1955).Search in Google Scholar
39 10.1016/j.tetlet.2004.05.002, S. Porwanski, S. Menuel, X. Marsura, A. Marsura. Tetrahedron Lett.45, 5027 (2004).Search in Google Scholar
40 10.1107/S002188980403225X, 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).Search in Google Scholar
41 G. M. Sheldrick. “SHELXL-97”, Program for the Refinement of Crystal Structures, University of Göttingen, Germany (1997).Search in Google Scholar
42 10.1107/S0021889899006020, L. J. Farrugia. J. Appl. Crystallogr.32, 837 (1999).Search in Google Scholar
43 10.1107/S0021889897003117, L. J. Farrugia. ORTEP3 for Windows, J. Appl. Crystallogr.30, 565 (1997).Search in Google Scholar
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