A convenient and practical approach to α-diketones via reactions of internal aryl alkynes with N-iodosuccinimide/water

Synthesis

Volumn , Issue 18, 2008, Pages 2879-2882

  Niu, Mingyu ^a   Fu, Hua ^a   Jiang, Yuyang ^a,b   Zhao, Yufen ^a  

^a Tsinghua University   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

diketones; Alkynes; Convenient and practical; N iodosuccinimide; Water

Indexed keywords

HYDROCARBONS; KETONES;

ALKYNES; CONVENIENT AND PRACTICAL; N-IODOSUCCINIMIDE; WATER;

ACETYLENE;

1 (2 BROMOPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (2 ETHYLPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 AMINOPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 CHLOROPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 METHOXYPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 (4 METHOXYPHENYL)OCTANE 1,2 DIONE; 1 (4 NITROPHENYL) 2 PHENYLETHANE 1,2 DIONE; 1 NAPHTHYL 2 PHENYLETHANE 1,2 DIONE; 1 PHENYL 2 (4 TOLY)ETHANE 1,2 DIONE; 1 PHENYLBUTANE 1,2 DIONE; 1,2 DICARBONYL DERIVATIVE; 1,2 DIPHENYLETHANE 1,2 DIONE; ALKYNE DERIVATIVE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; OXIDATION; ROOM TEMPERATURE;

EID: 53249136386     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067240     Document Type: Article

References (37)

1. (a) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron Lett. 1995, 40, 7305; and references therein.
2. (b) De Kimpe, N.; Stanoeva, E.; Boeykens, M. Synthesis 1994, 427; and references therein.
3. (a) Barta, T. E.; Stealey, M. A.; Collins, P. W.; Weier, R. M. Bioorg. Med. Chem. Lett. 1998, 8, 3443.
4. (b) Zhao, Z. J.; Wisnoski, D. D.; Wolkenberg, S. E.; Leister, W. H.; Wang, Y.; Lindsley, C. W. Tetrahedron Lett. 2004, 45, 4873.
5. (c) Held, I.; Xu, S. J.; Zipse, H. Synthesis 2007, 1185.
6. (d) Rong, F.; Chow, S.; Yan, S. Q.; Larson, G.; Hong, Z.; Wu, J. Bioorg. Med. Chem. Lett. 2007, 17, 1663.
7. (a) Bibaut-Renauld, C.; Burget, D.; Fouassier, J. P.; Varelas, C. G.; Thomatos, J.; Tsagaropoulos, G.; Ryrfors, L. O.; Karlsson, O. J. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3171.
8. (b) Ams, M. R.; Wilcox, C. S. J. Am. Chem. Soc. 2007, 129, 3966.
9. (a) Casey, C. P.; Guan, H. J. Am. Chem. Soc. 2007, 129, 5816.
10. (b) Procuranti, B.; Connon, S. J. Chem. Commun. 2007, 14, 1421.
11. (a) Naoki, K.; Nasuo, U. Bull. Chem. Soc. Jpn. 2001, 74, 755.
12. (b) Katritzky, A. R.; Zhang, D. Z.; Kirichenko, K. J. Org. Chem. 2005, 70, 3271; and references therein.
13. (a) Srinvasan, N. S.; Lee, D. G. J. Org. Chem. 1979, 44, 1574.
14. (b) Lee, D. G.; Chang, V. S. Synthesis 1978, 6, 462.
15. (a) Wolfe, S.; Pilgrim, W. R.; Garrad, T. F.; Chamberlain, P. Can. J. Chem. 1971, 49, 1099.
16. (b) Yusybov, M. S.; Filimonov, V. D. Synthesis 1991,131.
17. (c) Chi, K. W.; Yusubov, M. S.; Filimonov, V. D. Synth. Commun. 1994, 24, 2119.
18. (d) Foster, E. J.; Babuin, J.; Nguyen, N.; Williams, V. E. Chem. Commun. 2004, 18, 2052.
19. (a) McDonald, R. N.; Schwab, P. A. J. Am. Chem. Soc. 1964, 86, 4866.
20. (b) Aronovitch, C.; Tal, D.; Mazur, Y. Tetrahedron Lett. 1982, 23, 3623.
21. (a) Sheats, W. B.; Olli, L. K.; Stout, R.; Lundeen, J. T.; Justus, R.; Nigh, W. G. J. Org. Chem. 1979, 44, 4075.
22. (b) Che, C. M.; Yu, W. Y.; Chan, P. M.; Cheng, W. C.; Peng, S. M.; Lau, K. C.; Li, W. K. J. Am. Chem. Soc. 2000, 122, 11380.
23. (c) Giraud, A.; Provot, O.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Tetrahedron 2006, 62, 7667.
24. (d) Tummatom, J.; Khorphueng, P.; Petsom, A.; Muangsin, N.; Chaichitc, N.; Roengsumran, S. Tetrahedron 2007, 63, 11878.
25. (a) Dayan, S.; Ben-David, I.; Rozen, S. J. Org. Chem. 2000, 65, 8816.
26. (b) Wan, Z. H.; Jones, C. D.; Mitchell, D.; Pu, J. Y.; Zhang, T. Y. J. Org. Chem. 2006, 71, 26.
27. (a) Reed, S. F. Jr. J. Org. Chem. 1965, 30, 2195.
28. (b) Heasley, V. L.; Shellhamer, D. F.; Chappell, A. E.; Cox, J. M.; Hill, D. J.; McGovern, S. L.; Eden, C. C. J. Org. Chem. 1998, 63, 4433.
29. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
30. Chaikovskii, V. K.; Skorokhodov, V. I.; Filimonov, V. D. Russ. J. Org. Chem. 2001, 37, 1572.
31. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Bartoli, D. J. Org. Chem. 1991, 56, 4529.
32. Noh, T.; Choi, K.; Kwon, H.; Chang, D. J.; Park, B. S. Bull. Korean Chem. Soc. 1999, 20, 539.
33. Yi, X. B.; Wu, G. S.; Lu, F. C. Chin. J. Polym. Sci. 2002, 20, 219.
34. Yamamori, T.; Adachi, I. Tetrahedron Lett. 1980, 21, 1747.
35. Chang, C. L.; Kumar, M. P.; Liu, R. S. J. Org. Chem. 2004, 69, 2793.
36. Correia, J. J. Org. Chem. 1992, 57, 4555.
37. Nobrega, J. A.; Goncalves, S. M. C.; Peppe, C. Synth. Commun. 2002, 32, 3711.