Ionic Liquid Promoted One-pot Synthesis of Benzo[b][1,4]oxazines

Authors: Ebrahim Soleimani, Afsaneh Taheri Kal koshvandi

Abstract:

benzo[b][1,4]oxazines have been synthesized in good to excellent yields in the presence of the ionic liquid 1-butyl-3- methylimidazolium bromide [bmim]Br under relatively mild conditions without any added catalyst, the reaction workup is simple and the ionic liquid can be easily separated from the product and reused.

Keywords: Isocyanide, Benzo[b][1, 4]oxazines, Multi-componentreactions, [bmim]Br, Ionic Liquid.

Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1055092

References:

[1] Hermakens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678; (b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Foder, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
[2] Avendano, C.; Menendez, J. C. Medicinal Chemistry of Anticancer Drugs; Elsevier: 2008; (b) Doherty, A. M. Annual Reports in Medicinal Chemistry; Academic press: 2000; p 35. (c) Patrick, G. L. An Introduction to Medicinal Chemistry; Oxford University: 1995.
[3] Fringuelli, R.; Pietrella, D.; Schiaffella, F.; Guarrac, I. A.; Perito, S.; Bistoni, F.; Vecchiarelli, A. Bioorg. Med. Chem. 2002, 10, 1681-1686.
[4] Macchiarulo, A.; Costantino, G.; Fringuelli, F.; Vecchiarelli, A.; Schiaffella, F.; Fringuelli, R. Bioorg. Med. Chem. 2002, 10, 3415-3423.
[5] Adams, N. D.; Darcy, M. G.; Dhanak, D.; Duffy, K. J.; Fitch, D. M.; Knight, S. D.; Newlander, K. A.; Shaw, A. N. Int. Patent, WO 2006113432, 2006; Chem. Abstr. 2006, 145, 438652.
[6] Dömling, A. Chem. Rev. 2006, 106, 17-89; (b) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80; (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144; (d) Dömling, A.; Ugi, I. Angew.Chem., Int. Ed. 2000, 39, 3168-3210.
[7] Zhu, J.; Bienayme', H. Multicomponent Reactions, Wiley-VCH: Weinheim, Germany, 2005; (b) Ngouansavanh, T.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 5775-5778;(c)Laurent, E. K.; Gizolme, M.; Grimaud, L.; Oble, J. Org. Lett. 2006, 8, 4019-4021; (d) Tempest, P. A. Curr. Opin. Drug Discovery 2005, 8, 776-788; (e)Lu, K.; Luo, T.; Xiang, Z.; You, Z.; Fathi, R.; Chen, J.; Yang, Z. J. Comb. Chem. 2005, 7, 958-967.
[8] Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281; (b) Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765-769.
[9] Weber, L. Curr. Med. Chem., 2002, 9, 2085-2093.
[10] Dömling, A. Curr. Opin. Chem. Biol., 2002, 6, 306-313.
[11] Kitazume, T.; Ishizuka, T.; Takedu, M.; Itoh, K. Green Chem. 1999, 1, 221-223.
[12] Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Wasserscheid P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789; (c) Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391-1398; (d) Gordon, C. M. Appl. Catal. A: General 2001, 222, 101-117; (e) Sheldon, R. Chem. Commun.2001, 2399-2407.
[13] Shaabani, A.; Soleimani, E.; Maleki, A. Tetrahedron Lett. 2006, 47, 3031-3034; (b) Shaabani, A.; Soleimani, E.; Darvishi, M. Monatsh. Chem. 2007, 138, 43-46.
[14] Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. Mol. Divers. 2009, 13, 395-398.