Cesium carbonate promoted aerobic oxidation of arylacetamides: an efficient access to N-substituted α-keto amides

Tetrahedron Letters

Volumn 48, Issue 51, 2007, Pages 8982-8986

  Song, Bingrui ^a   Wang, Siyuan ^a   Sun, Caiyun ^a   Deng, Hongmei ^a   Xu, Bin ^a  

^a SHANGHAI UNIVERSITY   (China)

Author keywords

Keto amides; Arylacetamides; Atmospheric oxygen; Cesium carbonate; Oxidation

Indexed keywords

ACETAMIDE DERIVATIVE; ALPHA KETO AMIDE DERIVATIVE; AMIDE; BROMIDE; CESIUM; CESIUM CARBONATE; TETRA BUTYLAMMONIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

TETRA;

EID: 36248951143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.099     Document Type: Article

References (54)

1. Ozawa F., Soyama H., Yamamoto T., and Yamamoto A. Tetrahedron Lett. 23 (1982) 3383-3386
2. Mehdi S. Bioorg. Chem. 21 (1993) 249-259
3. Couve-Bonnaire S., Carpentier J.-F., Castanet Y., and Mortreux A. Tetrahedron Lett. 40 (1999)
4. Wong M.-K., Yu C.-W., Yuen W.-H., and Yang D. J. Org. Chem. 66 (2001) 3606-3609
5. Vecchietti V., Torre A.D., Lauria F., Castellino S., Monti G., Trane F., and Carneri I.D. Eur. J. Med. Chem. 9 (1974) 76-80
6. Scott M.K., Baxter E.W., Bennett D.J., Boyd R.E., Blum P.S., Codd E.E., Kukla J., Malloy E., Maryanoff B.E., Maryanoff C.A., Ortegon M.E., Rasmussen C.R., Reitz A.B., Renzi M.J., Schwender C.F., Shank R.P., Sherill R.G., Vaught J.L., Villani F.J., and Yim N. J. Med. Chem. 38 (1995) 4198-4210
7. Swindells D.C.N., White P.S., and Findlay J.A. Can. J. Chem. 56 (1978) 2491-2492
8. Tanaka H., Kuroda A., Marusawa H., Hatanaka H., Kino T., Goto T., Hashimoto M., and Taga T. J. Am. Chem. Soc. 109 (1987) 5031-5033
9. Bierer B.E., Mattila P.S., Standaert R.F., Herzenberg L.A., Burakoff S.J., Crabtree G., and Schreiber S.L. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 9231-9235
10. Schreiber S.L. Science 251 (1991) 283-287
11. Stocks M.J., Harrison R.P., and Teague S.J. Tetrahedron Lett. 36 (1995) 6555-6558
12. Hamilton G.S., and Steiner J.P. J. Med. Chem. 41 (1998) 5119-5143
13. Guo C.X., Reich S., Showalter R., Villafranca E., and Dong L. Tetrahedron Lett. 41 (2000) 5307-5311
14. Hudack Jr. R.A., Barta N.S., Guo C.X., Deal J., Dong L.M., Fay L.K., Caprathe B., Chatterjee A., Vanderpool D., Bigge C., Showalter R., Bender S., Augelli-Szafran C.E., Lunney E., and Hou X.J. J. Med. Chem. 49 (2006) 1202-1206
15. Ocain T.D., and Rich D.H. J. Med. Chem. 35 (1992) 451-456
16. Nakamura M., Inoue J., and Yamada T. Bioorg. Med. Chem. Lett. 10 (2000) 2807-2810
17. Papanikos A., Rademann J., and Meldal M. J. Am. Chem. Soc. 123 (2001) 2176-2181
18. Hua R.M., Takeda H.A., Abe Y., and Tanaka M. J. Org. Chem. 69 (2004) 974-976
19. Sheha M.M., Mahfouz N.M., Hassan H.Y., Youssef A.F., Mimoto T., and Kiso Y. Eur. J. Med. Chem. 35 (2000) 887-984
20. Kitagawa O., Takahashi M., Kohriyama M., and Taguchi T. J. Org. Chem. 68 (2003) 9851-9853
21. Han W., Hu Z.L., Jiang X.J., Wasserman Z.R., and Decicco C.P. Bioorg. Med. Chem. Lett. 13 (2003) 1111-1114
22. Radosevich A.T., Musich C., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 1090-1091
23. Takahashi K., Shibasaki K., Ogura K., and Iida H. Chem. Lett. 11 (1983) 859-862
24. Yang Z., Zhang Z.X., Meanwell N.A., Kadow J.F., and Wang T. Org. Lett. 4 (2002) 1103-1105
25. Zhu J.L., Wong H., Zhang Z.W., Yin Z.W., Kadow J.F., Meanwell N.A., and Wang T. Tetrahedron Lett. 46 (2005) 3587-3589
26. Sassatelli M., Bouchikhi F., Messaoudi S., Anizon F., Debiton E., Barthomeuf C., Prudhomme M., and Moreau P. Eur. J. Med. Chem. 41 (2006) 88-100
27. Buu-Hoi N.P., Saint-Ruf G., and Bourgeade J.C. J. Heterocycl. Chem. 5 (1968) 545-546
28. Chen Y.H., Zhang Y.H., Zhang H.J., Liu D.Z., Gu M., Li J.Y., Wu F., Zhu X.Z., Li J., and Nan F.J. J. Med. Chem. 49 (2006) 1613-1623
29. Zaleska B., and Lis S. Synth. Commun. 31 (2001) 189-197
30. Yoshifuji S., and Arakawa Y. Chem. Pharm. Bull. 37 (1989) 3380-3381
31. Wasserman H.H., and Ives J.L. J. Org. Chem. 50 (1985) 3573-3580
32. Ling K.Q., Ji G., Cai H., and Xu J.H. Tetrahedron Lett. 39 (1998) 2381-2384
33. Ling K.Q., Ye J.H., Chen X.Y., M D.J., and Xu J.H. Tetrahedron 55 (1999) 9185-9204
34. Ozawa F., Soyama H., Yanagihara H., Aoyama I., Takino H., Izawa K., Yamamoto T., and Yamamoto A. J. Am. Chem. Soc. 107 (1985) 3235-3245
35. Huang L., Ozawa F., and Yamamoto A. Organometallics 9 (1990) 2603-2611
36. Uozumi Y., Arii T., and Watanabe T. J. Org. Chem. 66 (2001) 5272-5274
37. Ugi I., and Fetzer U. Chem. Ber. 94 (1961) 1116-1121
38. Chen J.J., and Deshpande S.V. Tetrahedron Lett. 44 (2003) 8873-8876
39. Xu B., Stephens A., Kirschenheuter G., Greslin A., Cheng X., Sennelo J., Cattaneo M., Zighetti M., Chen A., Kim S.-A., Kim H.S., Bischofberger N., Cook G., and Jacobson K.A. J. Med. Chem. 45 (2002) 5694-5709
40. Kim H.S., Ohno M., Xu B., Kim H., Choi Y., Ji X.D., Maddileti S., Marquez V., Harden T.K., and Jacobson K.A. J. Med. Chem. 46 (2003) 4974-4987
41. Jacobson K.A., Constanzi S., Ohno M., Joshi B.V., Besada P., Xu B., and Tchillbon S. Curr. Top. Med. Chem. 4 (2004) 671-686
42. Pattabiraman V.R., Padakanti S., Veeramaneni V.R., Pal M., and Yeleswarapu K.R. Synlett (2002) 947-951
43. Pal M., Swamy N.K., Hameed P.S., Padakanti S., and Yeleswarapu K.R. Tetrahedron 60 (2004) 3987-3997
44. The starting materials 1a-n were synthesized according to the literatures:. Schumann J., Kanitz A., and Hartmann H. Synthesis (2002) 1268-1276
45. Huh D.H., Jeong J.S., Lee H.B., Ryu H., and Kim Y.G. Tetrahedron 58 (2002) 9925-9932
46. Shen W., and Kunzer A. Org. Lett. 4 (2002) 1315-1317
47. Bordwell F.G., and Fried H.E. J. Org. Chem. 56 (2004) 4218-4223
48. Bonanomi M., and Baiocchi L. Gazz. Chim. Ital. 119 (1989) 445-448
49. Kitahara Y., Mochii M., Mori M., and Kubo A. Tetrahedron 59 (2003) 2885-2891
50. Matsunaka K., Iwahama T., Sakaguchi S., and Ishii Y. Tetrahedron Lett. 40 (1999) 2165-2168
51. Zaborovskiy A.B., Lutsyk D.S., Prystansky R.E., Kopylets V.I., Timokhin V.I., and Chatgilialoglu C. J. Organomet. Chem. 689 (2004) 2912-2918
52. Harvey R.G., Abu-shqara E., and Yang C.X. J. Org. Chem. 57 (1992) 6313-6317
53. Park K.K., Tsou L.K., and Hamilton A.D. Synthesis (2006) 3617-3620
54. 2: C, 67.22; H, 6.94; N, 12.06. Found: C, 67.01; H, 6.945; N, 11.96.