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http://dx.doi.org/10.5012/bkcs.2009.30.6.1325

Solid-phase Synthesis of 7-Aryl-benzo[b][1,4]oxazin-3(4H)-one Derivatives on a BOMBA Resin Utilizing the Smiles Rearrangement  

Lee, Ji-Min (Center for High Throughput Synthesis Platform Technology, Korea Research Institute of Chemical Technology)
Yu, Eun-Ae (Center for High Throughput Synthesis Platform Technology, Korea Research Institute of Chemical Technology)
Park, Joo-Yeon (Center for High Throughput Synthesis Platform Technology, Korea Research Institute of Chemical Technology)
Ryu, In-Ae (Center for High Throughput Synthesis Platform Technology, Korea Research Institute of Chemical Technology)
Shin, Dong-Soo (Department of Chemistry, Changwon National University)
Gong, Young-Dae (Center for High Throughput Synthesis Platform Technology, Korea Research Institute of Chemical Technology)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.6, 2009 , pp. 1325-1330 More about this Journal
Abstract
A general method has been developed for the solid phase synthesis of drug-like 7-aryl-benzo[b][1,4]oxazin-3(4H)- one derivatives 6. The method relies on a novel, microwave irradiation promoted cyclization reaction of the BOMBA resin bound, N-substituted-$\alpha$-(2-chloro-4-bromophenoxy)acetamide 3 that takes place via a Smiles rearrangement. The 7-bromobenzo[1,4]oxazine 4, produced in this process is converted to 7-aryloxazin analogs 5 by utilizing Suzuki coupling with various substituted arylboronic acids. Finally, the target 7-aryl-benzo[b][1,4]oxazin-3(4H)-ones 6 are liberated from the resin by treatment with 5% TFA. The progress of the reactions involved in this preparative route can be monitored by using ATR-FTIR spectroscopy on a single bead. The target compounds, obtained by using this five-step sequence, are produced in high yields and purities.
Keywords
Solid-phase synthesis; Benzo[b][1,4]oxazin; Smiles rearrangement; Microwave irradiation; BOMBA resin;
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1 Adams, N. D.; Darcy, M. G.; Dhanak, D.; Duffy, K. J.; Fitch, D. M.; Knight, S. D.; Newlander, K. A.; Shaw, A. N. Chem. Abstr. 2006, 145, 438652.   DOI   ScienceOn
2 Hermakens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.   DOI   ScienceOn
3 Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Foder, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.   DOI   ScienceOn
4 Avendano, C.; Menendez, J. C. Medicinal Chemistry of Anticancer Drugs; Elsevier: 2008.
5 Doherty, A. M. Annual Reports in Medicinal Chemistry; Academic press: 2000; p 35.
6 Patrick, G. L. An Introduction to Medicinal Chemistry; Oxford University: 1995.
7 Ganellin, C. R.; Roberts, S. M. Medicinal Chemistry; Academic press: 1993.
8 Fringuelli, R.; Pietrella, D.; Schiaffella, F.; Guarrac, I. A.; Perito, S.; Bistoni, F.; Vecchiarelli, A. Bioorg. Med. Chem. 2002, 10, 1681.   DOI   ScienceOn
9 Macchiarulo, A.; Costantino, G.; Fringuelli, F.; Vecchiarelli, A.; Schiaffella, F.; Fringuelli, R. Bioorg. Med. Chem. 2002, 10, 3415.   DOI   ScienceOn
10 Hwang, J. Y.; Choi, H.-S.; Lee, D.-H.; Yoo, S.-E.; Gong, Y.-D. J. Comb. Chem. 2005, 7, 136.   DOI   ScienceOn
11 Hwang, J.-S.; Choi, H.-S.; Seo, J.-S.; La, H.-J.; Kim, D.-S.; Jeon, H. S.; Jeon, M.-K.; Lee, H. L.; Gong, Y.-D. J. Org. Chem. 2005, 70, 10151.   DOI   ScienceOn
12 Hwang, J. Y.; Choi, H.-S.; Gong, Y.-D. Tetrahedron Lett. 2005, 46, 3107.   DOI   ScienceOn
13 Lee, I. Y.; Kim. S. Y.; Lee, J. Y.; Yu, C.-M.; Lee, D. H.; Gong, Y.-D. Tetrahedron Lett. 2004, 45, 9319.   DOI   ScienceOn
14 Breznik, M.; Hrast, V.; Mrcina, A.; Kikelj, D. Tetrahedron: Asymmetry 1999, 10, 153.   DOI   ScienceOn
15 Gong, Y.-D.; Seo, J.-S.; Chon, Y. -S.; Hwang, J.-Y.; Park, J.-Y.; Yoo, S.-E. J. Comb. Chem. 2003, 5, 577.   DOI   ScienceOn
16 Lanni, Jr., T. B.; Greene, K. L.; Kolz, C. N.; Para, K. S.; Visnick, M.; Mobley, J. L.; Dudley, D. T.; Baginski, T. J.; Liimatta, M. B. Bioorg. Med. Chem. Lett. 2007, 17, 756.   DOI   ScienceOn
17 Breznik, M.; Mrcina, A.; Kikelj, D. Tetrahedron: Asymmetry 1998, 9, 1115.   DOI   ScienceOn
18 Ma, C.; Cho, S.-D.; Flack, J. R.; Shin, D.-S. Heterocycles 2004, 63, 75.   DOI   ScienceOn
19 Fivush, A. M.;Willson, T. M. Tetrahedron Lett. 1997, 38, 7151.   DOI   ScienceOn
20 Larsen, S. D.; Dipaolo, B. A. Org. Lett. 2001, 3, 3341.   DOI   ScienceOn
21 Pietta, P. G.; Cavallo, P. F.; Takahashi, K.; Marshall, G. R. J. Org. Chem. 1972, 39, 44.   DOI   ScienceOn
22 Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3404.   DOI
23 Zuo, H.; Meng, L.; Ghate, M.; Hwang, K. H.; Cho, Y. K.; Chandrasekhar, S.; Ch, R. R.; Shin, D.-S. Tetrahedron Lett. 2008, 49, 3827.   DOI   ScienceOn
24 Bunin, B. Combinatorial Index; Cloth. Academic Press: London, 1997; pp 219-220.   DOI   ScienceOn
25 Cho, S.-D.; Song, S.-Y.; Park, Y.-D.; Kim, J.-Y.; Joo, W.-H.; Shiro, M.; Falck, J. R.; Shin, D.-S.; Yoon, Y.-J. Tetrahedron Lett. 2003, 44, 8995.   DOI   ScienceOn
26 Cho, S.-D.; Song, S.-Y.; Park, Y.-D.; Kim, J.-Y.; Joo, W.-H.; Shiro, M.; Esser, L.; Falck, J. R.; Ahn, C.; Shin, D.-S.; Yoon, Y.-J. Tetrahedron 2004, 60, 3763.   DOI   ScienceOn
27 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
28 Seo, J.-S.; Yoon, C. M.; Gong, Y.-D. J. Comb. Chem. 2005, 9, 366.   DOI   ScienceOn
29 Lee, C. L.; Chan, K. P.; Lam, Y.; Lee, S. Y. Tetrahedron Lett. 2001, 42, 1167.   DOI   ScienceOn
30 Breznik, M.; Grdadolnik, S. G.; Giester, G.; Leban, I.; Kikelj, D. J. Org. Chem. 2001, 66, 7044.   DOI   ScienceOn
31 Schanche, J.-S. Molecular Diversity 2003, 7, 293.
32 Cho, S.-D.; Park, Y.-D.; Kim, S.-G.; Chen, M.; Song, S.-Y.; Joo, W.-H.; W.-H.; Falck, J. R.; Shiro, M.; Shin, D.-S.; Yoon, Y.-J. J. Org. Chem. 2003, 68, 7918.   DOI   ScienceOn