Syntheses of N-alkylated carbazolones via Pd(OAc)2-mediated intramolecular coupling of N-substituted 3-(arylamino)cyclohex-2-enones

Synlett

Volumn , Issue 19, 2010, Pages 2899-2904

  Bi, Wenying ^a   Yun, Xiliu ^a   Fan, Yanfeng ^a   Qi, Xiuxiang ^a   Du, Yunfei ^a   Huang, Jianhui ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

CH activation; N alkylated carbazolones; N substituted 3 (arylamino)cyclohex 2 enones; oxygen; Pd(OAc)2

Indexed keywords

3 (ARYLAMINO)CYCLOHEX 2 ENONE DERIVATIVE; ALICYCLIC COMPOUND; CARBAZOLE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ALKYLATION; ANNULATION REACTION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; OXIDATION; SOLVENT EFFECT; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 78650179139     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259027     Document Type: Article

References (45)

1. Gant T G., Sarshar S, US 2010119623 2010, Barta T E., Barabasz A F., Foley B E., Geng L, Hall S E., Hanson G J., Jenks M, Ma W, Rice J W., Veal J, Bioorg. Med. Chem. Lett. 2009 19 3078
2. Barta T E., Veal J M., Rice J W., Partridge J M., Fadden R P., Ma W, Jenks M, Geng L, Hanson G J., Huang K H., Barabasz A F., Foley B E., Otto J, Hall S E., Bioorg. Med. Chem. Lett. 2008 18 3517
3. Yan S, Wu H, Wu N, Jiang Y, Synlett 2007 2699
4. Romeo G, Materia L, Pittala V, Modica M, Salerno L, Siracusa M, Russo F, Minneman K P., Bioorg. Med. Chem. 2006 14 5211
5. Li X, Vince R, Bioorg. Med. Chem. 2006 14 2942
6. Kukushkin S Y., Ivanov P Y., Alekseeva L M., Levina V I., Kobrakov K I., Grigorev N B., Granik V G., Russ. Chem. Bull. 2005 54 1887
7. Sorensen U S., Pombo-Villar E, Helv. Chim. Acta 2004 87 82
8. Bunce R A., Nammalwar B, J. Heterocycl. Chem. 2009 46 172
9. Scott T L., Burke N, Carrero-Martínez G, Söderberg B C. G., Tetrahedron 2007 63 1183
10. Scott T L., Yu X, Gorugantula S P., Carrero-Martinez G, Soederberg B C. G., Tetrahedron 2006 62 10835
11. Czeskis B A., Wheeler W J., J. Labelled Compd. Radiopharm. 2005 48 407
12. Sissouma D, Collet S C., Guingant A Y., Synlett 2004 2612
13. Scott T L., Söderberg B C. G., Tetrahedron 2002 43 1621
14. Tietcheu C, Garcia C, Gardette D, Dugat D, Gramain J, J. Heterocycl. Chem. 2002 39 965
15. Dubois E A., vandenBos J C., Doornbos T, van Doremalen P, Somsen G A., Vekemans J, Janssen A, Batink H D., Boer G J., Pfaffendorf M, vanRoyen E A., vanZwieten P A., J. Med. Chem. 1996 39 3256
16. Caubère C, Caubère P, Renard P, Bizot-Espiart J.-G, Jamart-Grégoire B, Tetrahedron Lett. 1993 34 6889
17. Oikawa Y, Yonemitsu O, J. Org. Chem. 1977 42 1213
18. Kawai H, Nagasu T, Takeda T, Fujiwara K, Tsuji T, Ohkita M, Nishida J, Suzuki T, Tetrahedron Lett. 1975 45 4533
19. Weng B, Liu R, Li J.-H, Synthesis 2010 in press
20. Punniyamurthy T, Velusamy S, Iqbal J, Chem. Rev. 2005 105 2329
21. Knölker H.-J, Reddy K R., Chem. Rev. 2002 102 4303
22. Hagelin H, Oslob J D., Åkermark B, Chem. Eur. J. 1999 5 2413
23. Knölker H.-J, Fröhner W, J. Chem. Soc., Perkin Trans. 1 1998 173
24. Kudzma L V., Synlett 2003 1661
25. Osuka A, Mori Y, Suzuki H, Chem. Lett. 1982 2031
26. Iida H, Yuasa Y, Kibayashi C, J. Org. Chem. 1980 45 2938
27. Iida H, Yuasa Y, Kibayashi C, J. Org. Chem. 1979 44 1236
28. Ge H, Niphakis M J., Georg G I., J. Am. Chem. Soc. 2008 130 3708
29. Rakshit S, Patureau F W., Glorius F, J. Am. Chem. Soc. 2010 132 9585
30. Neumann J J., Suri M, Glorius F, Angew. Chem. Int. Ed. 2010 49 In press
31. Shi Z, Zhang C, Li S, Pan D, Ding S, Cui Y, Jiao N, Angew. Chem. Int. Ed. 2009 48 4572
32. Würtz S, Rakshit S, Neumann J J., Dröge T, Glorius F, Angew. Chem. Int. Ed. 2008 47 7230
33. Humphrey G R., Kuethe J T., Chem. Rev. 2006 106 2875
34. Cacchi S, Fabrizi G, Chem. Rev. 2005 105 2873
35. Chen C, Lieberman D R., Larsen R D., Verhoeven T R., Reider P J., J. Org. Chem. 1997 62 2676
36. Koerber-Plé K, Massiot G, Synlett 1994 759
37. Sakamoto T, Nagano T, Kondo Y, Yamanaka H, Synthesis 1990 215
38. For recent selected examples using oxygen as oxidant, see:, Hamada T, Ye X, Stahl S S., J. Am. Chem. Soc. 2008 130 833
39. Jiao N, Zhang C, J. Am. Chem. Soc. 2010 132 28
40. Shi Z, Zhang B, Cui Y, Jiao N, Angew. Chem. Int. Ed. 2010 49 4036
41. Jiao N, Zhang C, Angew. Chem. Int. Ed. 2010 49 6174
42. For the most similar N-methylation of 1 using NaH and methyl iodide in toluene, see:, Aragon P.-J, Yapi A.-D, Pinguet F, Chezal J.-M, Teulade J.-C, Chapat J.-P, Blache Y, Chem. Pharm. Bull. 2004 52 659
43. Sissouma D, Collet S C., Guingant A Y., Synlett 2004 2612
44. Dobbs A P., Jones K, Veal K T., Tetrahedron Lett. 1997 38 5379
45. Rodríguez J G., delValle C, Esteban-Calderón C, Martinez-Ripoll M, J. Chem. Crystallogr. 1995 25 249