A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides

Tetrahedron Letters

Volumn 52, Issue 26, 2011, Pages 3287-3290

  Majce, Vita ^a   Kočevar, Marijan ^a   Polanc, Slovenko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Amine catalysis; Fumaramides; Isomerization; Microwave irradiation

Indexed keywords

ACETONITRILE; AMIDE; FUMARAMIDE DERIVATIVE; FUMARIC ACID DERIVATIVE; MALEIC ACID DERIVATIVE; PIPERIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG PURITY; ISOMERIZATION; MICROWAVE RADIATION; QUANTITATIVE ANALYSIS; REACTION TIME;

EID: 79957610936     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.066     Document Type: Article

References (35)

1. V. Balasubramaniyan, V.G. Bhatia, and S.B. Wagh Tetrahedron 39 1983 1475 1485
2. M.M. Baag, A. Kar, and N.P. Argade Tetrahedron 59 2003 6489 6492
3. S.M. Spatz, and H. Stone J. Org. Chem. 23 1958 1559 1560
4. V. Balasubramaniyan, and N.P. Argade Ind. J. Chem. B 26B 1987 476 477
5. A.R. Hands J. Chem. Soc. 1964 1181 1182
6. R. Callahan, R. Prip, N. Shariff, O. Sklyut, R. Rothchild, and K. Bynum Appl. Spectrosc. 59 2005 354 365
7. Jumina, A.K. Zulkarnain, and P. Mulyono Indonesian J. Pharm. 16 2005 116 123
8. K. Nozaki J. Am. Chem. Soc. 1941 2681 2683
9. H. Junek, N.M. Jacobson, P. Wiedner, K. Nordberg, and H. Rauch-Puntigam Monatsh. Chem. 109 1978 395 404
10. C. Griehl, D. Strohl, H. Jeschkeiet, and E. Kleinpeter Monatsh. Chem. 123 1992 647 654
11. A. Kolbe, C. Griehl, and S. Biehler J. Mol. Struct. 661-662 2003 239 246
12. G. Gupta, and S.B. Wagh Ind. J. Chem. B 45B 2006 697 702
13. Tao, C.; Wang, Q.; Trieu, V.; Desai, N.; Soon-Shiong, P. PCT Int. Appl., 2008064060; Chem. Abstr. 2008, 149, 9382.
14. A. Sanchez, E. Pedroso, and A. Grandas Eur. J. Org. Chem. 2010 2600 2606
15. L. Frkanec, M. Jokić, J. Makarević, K. Wolsperger, and M. Zinić J. Am. Chem. Soc. 124 2002 9716 9717
16. G. Bottari, D.A. Leigh, and E. Perez J. Am. Chem. Soc. 125 2003 13360 13361
17. G. Bottari, F. Dehez, D.A. Leigh, P.J. Nash, E.M. Perez, J.K.Y. Wong, and F. Zerbetto Angew. Chem., Int. Ed. 42 2003 5886 5889
18. Y. Li, H. Li, Y. Li, H. Liu, S. Wang, X. He, N. Wang, and D. Zhu Org. Lett. 7 2005 4835 4838
19. F.-Y. Ji, L.-L. Zhu, X. Ma, Q.-C. Wang, and H. Tian Tetrahedron Lett. 50 2009 597 600
20. M. Augustin, and M. Kohler Tetrahedron 32 1976 2141 2145
21. M.T.W. Hearn, and A.D. Ward Aust. J. Chem. 30 1977 2031 2043
22. J. Košmrlj, M. Kočevar, and S. Polanc Synlett 2009 2217 2235
23. A. Kovač, V. Majce, R. Lenaršič, S. Bombek, J.M. Bostock, I. Chopra, S. Polanc, and S. Gobec Bioorg. Med. Chem. Lett. 17 2007 2047 2054
24. A. Di Stefano, P. Sozio, A. Iannitelli, C. Marianecci, E. Santucci, and M. Carafa J. Drug Targeting 14 2006 652 661
25. R.E. Kleiner, C.E. Dumelin, G.C. Tiu, K. Sakurai, and D.R. Liu J. Am. Chem. Soc. 132 2010 11779 11791
26. A. Breuning, B. Degel, F. Schulz, C. Buchold, M. Stempka, U. Machon, S. Heppner, C. Gelhaus, M. Leippe, M. Leyh, C. Kisker, J. Rath, A. Stich, J. Gut, P.J. Rosenthal, C. Schmuck, and T. Schirmeister J. Med. Chem. 53 2010 1951 1963
27. U. Machon, C. Buchold, M. Stempka, T. Schirmeister, C. Gelhaus, M. Leippe, J. Gut, P.J. Rosenthal, C. Kisker, M. Leyh, and C. Schmuck J. Med. Chem. 52 2009 5662 5672
28. J.B. Smaill, H.D. Hollis Showalter, H. Zhou, A.J. Bridges, D.J. McNamara, D.W. Fry, J.M. Nelson, V. Sherwood, P.W. Vincent, B.J. Roberts, W.L. Elliott, and W.A. Denny J. Med. Chem. 44 2001 429 440
29. I.L. Pinto, R.L. Jarvest, B. Clarke, C.E. Dabrowski, A. Fenwick, M.M. Gorczyca, L.J. Jennings, P. Lavery, E.J. Sternberg, D.G. Tew, and A. West Bioorg. Med. Chem. Lett. 9 1999 449 452
30. 3: C, 64.38; H, 5.40; N, 6.83. Found: C, 64.41; H, 5.14; N, 6.79.
31. 2: C, 73.45; H, 6.16; N, 9.52. Found: C, 73.20; H, 6.17; N, 9.39.
32. For the equipment applied here and the methodology in general, see, for example: N. Maraš, S. Polanc, and M. Kočevar Tetrahedron 64 2008 11618 11624
33. J. Hren, F. Požgan, A. Bunič, V.I. Parvulescu, S. Polanc, and M. Kočevar Tetrahedron 65 2009 8216 8221
34. K. Kranjc, and M. Kočevar Curr. Org. Chem. 14 2010 1050 1074
35. 2: C, 73.45; H, 6.16; N, 9.52. Found: C, 73.34; H, 5.98; N, 9.51.