A rapid and direct access to symmetrical/unsymmetrical 3,4-diarylmaleimides and pyrrolin-2-ones

Tetrahedron

Volumn 60, Issue 18, 2004, Pages 3987-3997

  Pal, Manojit ^a   Swamy, Nalivela Kumara ^a   Hameed, P Shahul ^a   Padakanti, Srinivas ^a   Yeleswarapu, Koteswar Rao ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

3,4 Diarylmaleimide and pyrrolin 2 one; Oxidative cyclization; Oxygen; Phenacyl amide

Indexed keywords

1,8 DIAZABICYCLO[5.4.0]UNDEC 7 ENE; ALKENE DERIVATIVE; AMIDE; CELECOXIB; KETONE DERIVATIVE; MALEIMIDE DERIVATIVE; PYRROLINE DERIVATIVE; ROFECOXIB; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SELECTIVITY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR INTERACTION; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 1842814005     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.03.036     Document Type: Article

References (50)

1. For reviews, see (a) Reitz D.B., Isakson P.C. Curr. Pharm. Des. 1:1995;211-220.
2. Carter J.S. Exp. Opin. Ther. Pat. 8:1997;21-29.
3. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., Isakson P.C. J. Med. Chem. 40:1997;1347-1365.
4. Prasit P., Wang Z., Brideau C., Chan C.-C., Charleson S., Cromlish W., Ethier D., Evans J.F., Ford-Hutchinson A.W., Gauthier J.Y., Gordon R., Guay J., Gresser M., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neill G.P., Ouellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Therien M., Vickers P., Wong E., Xu L.J., Young R.N., Zamboni R., Boyce S., Rupniak N., Forrest M., Visco D., Patrick D. Bioorg. Med. Chem. Lett. 9:1999;1773-1778.
5. Bosch J., Roca T., Catena J.-L., Llorens O., Perez J.-J., Lagunas C., Fernandez A.G., Miquel I., Fernandez-Serrat A., Farrerons C. Bioorg. Med. Chem. Lett. 10:2000;1745-1748.
6. Jackson L.M., Hawkey C.J. Expert Opin. Invest. Drugs. 8:1999;963-971.
7. Khanna I.K., Weier R.M., Yu Y., Collins P.W., Miyashiro J.M., Koboldt C.M., Veenhuizen A.W., Currie J.L., Seibert K., Isakson P.C. J. Med. Chem. 40:1997;1619-1633.
8. Pal, M.; Rao, Y. K.; Rajagopalan, R.; Misra, P.; Kumar, P. M.; Rao, C. S. World Patent WO 01/90097, Nov 29, 2001; Chem. Abstr. 2002, 136, 5893.
9. Pattabiraman V.R., Padakanti P.S., Veeramaneni V.R., Pal M., Yeleswarapu K.R. Synlett. 2002;947-951.
10. Padakanti S., Veeramaneni V.R., Pattabiraman V.R., Pal M., Yeleswarapu K.R. Tetrahedron Lett. 43:2002;8715-8719.
11. Pal M., Rao V.V., Srinivas P., Murali N., Akhila V., Premkumar M., Rao C.S., Misra P., Ramesh M., Rao Y.K. Indian J. Chem. 42B:2003;593-601.
12. Pal M., Veeramaneni V.R., Nagaballi M., Kalleda S.R., Misra P., Casturi S.R., Yeleswarapu K.R. Bioorg. Med. Chem. Lett. 13:2003;1639-1643.
13. Pal M., Madan M., Srinivas P., Pattabiraman V.R., Kalleda S.R., Akhila V., Ramesh M., Rao Mamidi N.V.S., Casturi S.R., Malde A., Gopalakrishnan B., Yeleswarapu K.R. J. Med. Chem. 46:2003;3975-3984.
14. Casturi, S. R.; Yeleswarapu, K. R; Pal, M.; Padakanti, S.; Datla, S. R.; Hegde, P.; Mamnoor, P.; Kumar, S.; Ramanujam, R. Presented at the 6th World Congress on Inflammation, August 2-6; Vancouver, Canada, 2003; Abstract No. 154, FL0540.
15. Ichikawa, Y; Shiyoji, M. Jpn. Kokai Tokkyo Koho JP 08231502 A2, Sep 10, 1996, 25 pp; Chem Abstr. 1996, 125, 300818.
16. Kanaoka Y. Angew. Chem., Int. Ed. Engl. 16:1977;137-140.
17. Rajasekharan K.N., Mayadevi M., Burke M. J. Biol. Chem. 264:1989;10810-10819.
18. Corrie J.T.E., Munasinghe V.R.N., Rettig W. J. Heterocycl. Chem. 37:2000;1447-1455.
19. Goes M., Lauteslager X.Y., Verhoeven J.W., Hofstraat J.W. Eur. J. Org. Chem. 1998;2373-2377.
20. Verhey H.J., Bekker C.H.W., Verhoeven J.W., van der Ven L.G.J., Hofstraat J.W. Polymer. 38:1997;4491-4497.
21. Kalgutkar A.S., Crews B.C., Marnett L.J. J. Med. Chem. 39:1996;1692-1703.
22. Davis P.D., Bit R.A., Hurst S.A. Tetrahedron Lett. 31:1990;2353-2356. and references cited therein.
23. Smith D.G., Buffet M., Fenwick A.E., Haigh D., Ife R.J., Saunders M., Slingsby B.P., Stacey R., Ward R.W. Bioorg. Med. Chem. Lett. 11:2001;635-639.
24. Zhu G., Conner S., Zhou X., Shih C., Brooks H.B., Considine E., Dempsey J.A., Ogg C., Patel B., Schultz R.M., Spencer C.D., Teicher B., Watkins S.A. Bioorg. Med. Chem. Lett. 13:2003;1231-1235.
25. Beccalli E.M., Gelmi M.L., Marchesini A. Eur. J. Org. Chem. 6:1999;1421-1426.
26. Terpin A., Polborn K., Steglich W. Tetrahedron. 51:1995;9941-9946.
27. Fields E.K., Behrend S.J., Meyerson S., Winzenburg M.L., Ortega B.R., Hall H.K. Jr. J. Org. Chem. 55:1990;5165-5170.
28. Davis P.D., Bit R.A. Tetrahedron Lett. 31:1990;5201-5204.
29. Brenner M., Rexhausen H., Steffan B., Steglich W. Tetrahedron. 44:1988;2887-2892.
30. Koelsch C.F., Wawzonek S. J. Org. Chem. 6:1941;684-689.
31. Marminon C., Pierre A., Pfeiffer B., Perez V., Leonce S., Renard P., Prudhomme M. Bioorg. Med. Chem. 11:2003;679-687.
32. Faul M.M., Winneroski L.L., Krumrich C.A. Tetrahedron Lett. 40:1999;1109-1112.
33. Cook A.H., Linstead R.P. J. Chem. Soc. 1937;929-934.
34. Takahashi M., Nozaki C., Shibazaki Y. Chem. Lett. 1987;1229-1232.
35. Scudi J.V., Lindwall H.G. J. Am. Chem. Soc. 57:1935;2302-2303.
36. Davis P.D., Bit R.A., Hurst S.A. Tetrahedron Lett. 31:1990;2353-2356. and references cited therein.
37. Ichikawa, Y; Shiyoji, M. Jpn. Kokai Tokkyo Koho JP 08231502 A2, Sep 10, 1996, 25 pp; Chem Abstr. 1996, 125, 300818.
38. See Ref. 4b and references therein.
39. Yeh H.-C., Wu W.-C., Chen C.-T. Chem. Commun. 2003;404-405.
40. For earlier synthesis of 3,4-diaryl pyrrolin-2-one, see: (a) Ohshiro Y., Nanimoto H., Tanaka H., Komatsu M., Agawa T., Yasuoka N., Kai Y., Kasai N. Tetrahedron Lett. 26:1985;3015-3018. See also Ref. 3a.
41. Veeramaneni V.R., Pal M., Yeleswarapu K.R. Tetrahedron. 59:2003;3283-3290.
42. Coskun N., Tirli F. Synth. Commun. 27:1997;1-9.
43. Brideau C., Kargman S., Liu S., Dallob A.L., Ehrich E.W., Rodger I.W., Chan C.-C. Inflamm. Res. 45:1996;68-74.
44. Borah H.N., Boruah R.C., Sandhu J.S. J. Chem. Soc., Chem. Commun. 3:1991;154-155.
45. Khetan S.M., George M.V. Tetrahedron. 25:1969;527-540.
46. Porretta G.C., Biava M., Fioravanti R., Fischetti M., Melino C., Venza F., Bolle P., Tita B. Eur. J. Med. Chem. Chim. Ther. 27:1992;717-722.
47. Barton D.H.R., Chen Y., Tachdjian C. Heterocycles. 37:1994;793-805.
48. Busch M., Straetz F. J. Prakt. Chem. 150:1937;1-39.
49. Prakash O., Rani N., Goyal S. Indian J. Chem., Sect. B. 31:1992;349-350.
50. Minami T., Agawa T. J. Org. Chem. 39:1974;1210-1215.