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http://dx.doi.org/10.5012/bkcs.2013.34.6.1735

Efficient Synthesis of Spirobarbiturates and Spirothiobarbiturates Bearing Cyclopropane Rings by Rhodium(II)-Catalyzed Reactions of Cyclic Diazo Compounds  

Wang, Xue (School of Chemical Engineering, Yeungnam University)
Lee, Yong Rok (School of Chemical Engineering, Yeungnam University)
Publication Information
Abstract
Rhodium(II)-catalyzed reactions of cyclic diazo compounds derived from barbituric acid and thiobarbituric acid with a variety of styrene moieties were examined. These reactions provide rapid synthetic routes to the preparations of spirobarbiturates and spirothiobarbiturates bearing cyclopropane rings.
Keywords
Rhodium(II)-catalyzed reactions; Spirobarbiturates; Spirothiobarbiturates; Diazo compounds;
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1 Uhlmann, C.; Froscher, W. CNS Neurosci. Ther. 2009, 15, 24.   DOI   ScienceOn
2 Lomlin, L.; Einsiedel, J.; Heinemann, F. W.; Meyer, K.; Gmeiner, P. J. Org. Chem. 2008, 73, 3608.   DOI   ScienceOn
3 Galati, E. M.; Monforte, M. T.; Miceli, N.; Raneri, E. Famaco 2001, 56, 459.
4 Renard, A.; Lhomme, J.; Kotera, M. J. Org. Chem. 2002, 67, 1307.
5 Fraser, W.; Suckling, C. J.; Wood, H. C. S. J. Chem. Soc., Perkin Trans 1 1990, 3137.
6 Singh, P.; Paul, K. J. Heterocyclic Chem. 2006, 43, 607.   DOI
7 Ming, Y.; Wamhoff, H. Chem. Ber. 1987, 120, 1433.   DOI
8 Lee, Y. R.; Hwang, J. C. Eur. J. Org. Chem. 2005, 1568.
9 Lee, Y. R.; Suk, J. Y. Tetrahedron 2002, 58, 2359.   DOI   ScienceOn
10 Lee, Y. R.; Suk, J. Y. Tetrahedron Lett. 2000, 41, 4795.   DOI   ScienceOn
11 Lee, Y. R.; Suk, J. Y.; Kim, B. S. Tetrahedron Lett. 1999, 40, 8219.   DOI   ScienceOn
12 Lee, Y. R.; Suk, J. Y.; Kim, B. S. Tetrahedron Lett. 1999, 40, 6603.   DOI   ScienceOn
13 Lee, Y. R.; Suk, J. Y. Chem. Commun. 1998, 2621.
14 Lee, Y. R.; Kim, D. H. Tetrahedron Lett. 2001, 42, 6561.   DOI   ScienceOn
15 Lee, Y. R.; Cho, B. S.; Kwon, H. J. Tetrahedron 2003, 59, 9333.   DOI   ScienceOn
16 Lee, Y. R.; Choi, J. H. Bull. Korean Chem. Soc. 2006, 27, 503.   DOI   ScienceOn
17 Taber, D. F.; Ruckle, R. E., Jr.; Hennessy, M. J. J. Org. Chem. 1986, 51, 4077.   DOI
18 Naguib, F. N.; Levesque, D. L.; Wang, E.-C.; Panzica, R. P.; el Kouni, M. H. Biochem. Pharmacol. 1993, 46, 1273.   DOI   ScienceOn
19 Pietruszka, J. Chem. Rev. 2003, 103, 1051.   DOI   ScienceOn
20 Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.   DOI   ScienceOn
21 Faust, R. Angew. Chem., Int. Ed. 2001, 40, 2251.   DOI
22 Salaun, J. Top. Curr. Chem. 2000, 207, 1.   DOI
23 Reissig, H. U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.   DOI   ScienceOn
24 Yamaguchi, K.; Kazuta, Y.; Hirano, K.; Yamada, S.; Matsuda, A.; Shuto, S. Bioorg. Med. Chem. 2008, 16, 8875.   DOI   ScienceOn
25 Yoshida, S.; Rosen, T. C.; Sloan, M. J.; Meyer, O. G. J.; Ye, S.; Haufe, G.; Kirk, K. L. Bioorg. Med. Chem. 2004, 12, 2645.   DOI   ScienceOn
26 Salaun, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
27 Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117   DOI   ScienceOn
28 Cousins, G. S.; Hoberg, J. O. Chem. Soc. Rev. 2000, 29, 165.   DOI
29 Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.   DOI
30 Piers, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 971.
31 Nonhebel, D. C. Chem. Soc. Rev. 1993, 347.
32 Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73.   DOI
33 Doyle, M. P.; McKervey, M. A.; Ye, T. Morden Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley; New York, 1988.
34 Nishiyama, H. In Rhutenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinheim, 2004; p 179.
35 Hu, W.; Timmons, D. J.; Doyle, M. P. Org. Lett. 2002, 4, 901.   DOI   ScienceOn
36 Davies, H. M. L.; Walji, A. M. In Morden Rhodium- Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; p 341.
37 Doyle, M. P. Angew. Chem. Int. Ed. 2009, 48, 850.   DOI   ScienceOn
38 Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1.
39 Brackmann, F.; de Meijiere, A. Chem. Rev. 2007, 107, 4493.   DOI   ScienceOn
40 Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625.   DOI   ScienceOn
41 Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.   DOI   ScienceOn
42 Elinson, M. N.; Vereshchagin, A. N.; Stepanov, N. O.; Zaimovskaya, T. A.; Merkulova, V. M.; Nikishin, G. I. Tetrahedron Lett. 2010, 51, 428.   DOI   ScienceOn
43 Ray, R.; Krishna, S. H.; Sharma, J. D.; Limaye, S. N. Asian. J. Chem. 2007, 19, 2497.
44 Brunton, L. L.; Lazo, J. S.; Lazo, P.; Keith, L. Goodman & Gilman's The Pharmacological Basis of Therapeutics, 11th ed.; McGraw-Hill, 2006.
45 Maquoi, E.; Sounni, N. E.; Devy, L.; Oliver, F.; Frankenen, F.; Krell, H.-W.; Grams, F.; Foidart, J. M.; Noel, A. Clin. Cancer Res. 2004, 10, 4038.   DOI   ScienceOn
46 Grams, F.; Brandstetter, H.; D'Alo, S.; Gepperd, D.; Krell, H.-W.; Leinert, H.; Livi, V.; Menta, E.; Oliva, A.; Zimmermann, G. Biol. Chem. 2001, 382, 1277.