A convenient copper-catalyzed direct animation of nitroarenes with 9-alkylhydroxylamines

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1999, Pages 1437-1444

  Seko, Shinzo ^a   Miyake, Kunihito ^a   Kavvamura, Norio ^a  

^a Organic Synthesis Research Laboratory   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746405601     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901537j     Document Type: Article

References (56)

1. M. J. Astle, Industrial Organic Nitrogen Compounds, Reinhold Publishing Corp., New York, 1961, p. 83.
2. L. Schmerling, US 2 948 755/1960 (Chem. Abstr., 1961, 55, l 527g);
3. E. N. Squire, DE 2 114 254/1971 (Chem. Abstr., 1972, 76, 24 892n);
4. P. Kovacic, in Friedel Crafts and Related Reactions, ed. G. A. Olah, John Wiley & Sons, Inc., N.ew York, 1964, Vol. Ill, part 2, p. 1493;
5. F. Minisci, R. Galli and M, Cecere, Tetrahedron Lett., 1965, 4663;
6. G. G. Arzoumanidis and F. C. Rauch, J. Chem. Soc, Chem. Commun., 1973, 666;
7. J. I. G. Cadogan and A. G. Rowley, J. Chem. Soc., Perkin Trans. 1, 1975, 1069;
8. K. Shudo, T. Ohta and T. Okamoto, J. Am. Chem. Soc., 1981, 103, 645;
9. G. A. Olah and T. D. Ernst, J. Org. Chem., 1989, 54, 1203;
10. R. A. Abramovitch, J. M. Beckert, P. Chinnasamy, H. Xiaohua, W. Pennington and A. R. V. Sanjivamurthy, Heterocycles, 1989, 28, 623;
11. N. R. Ayyangar, S. N. Naik and K. V. Srinivasan, Tetrahedron Lett., 1990, 31, 3217;
12. H. Takeuchi, T. Adachi and H. Nishiguchi, J. Chem. Soc, , Chem. Commun., 1991, 1524;
13. H. Mitchell and Y. Leblanc, J. Org. Chem., 1994, 59, 682;
14. M. Wozniak, M. Grzegozek, W. Roszkiewicz and B. Szpakiewicz, Reel. Trav. Chim. Pays-Bas, 1995, 114, 13;
15. M. K. Stern, B. K. Cheng and J. Clark, New J. Chem., 1996, 20, 259 and references cited therein.
16. J. Golinski and M. Makosza, Tetrahedron Lett., 1978, 3495;
17. M. Makosza and T. Glinka, J. Org. Chem., 1983, 48, 3860;
18. M. Makosza and K. Wojciechowski, LiebigsAnn.IRecl., 1997, 1805.
19. F. Terrier, Nucleophilic Aromatic Displacement: the Influence of the Nitro Group, VCH Publishers, Inc., New York, 1991, p. 257;
20. O. N. Chupakhin, V. N. Charushin and H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, San Diego, 1994, p. 1.
21. M. Makosza and J. Winiarski, Ace, Chem. Res., 1987, 20, 282.
22. M. Makosza and K. Sienkiewicz, J. Org. Chem., 1990, 55, 4979; 1998, 63, 4199.
23. (a) A. R. Katritzky and K. S. Laurenzo, J. Org. Chem., 1986, 51, 5039; 1988, 53, 3978;
24. (b) M. Makosza and M. Bialecki, J. Org. Chem., 1992, 57, 4784;
25. M. Makosza and M. Bialecki, J. Org. Chem., 1998, 63, 4878;
26. P. F. Pagoria, A. R. Mitchell and R. D. Schmidt, J. Org. Chem., 1996, 61, 2934.
27. (a) J. Meisenheimer and E. Patzig, Chem. Ber., 1906, 39, 2533;
28. (b) C. C. Price and S.-T. Voong, Org. Synth., 1955, Coll. Vol. III, 664;
29. H. E. Baumgarten, J. Am. Chem. Soc., 1955, 77, 5109;
30. M. Hasegawa and T. Okamoto, Yakugaku Zasshi, 1973, 93, 1024 (Chem. Abstr., 1973, 79, 104 485j);
31. (e) R. Nasielski-Hinkens, J. Kotel, T. Lecloux and J. Nasielski, Synth. Commun., 1989, 19, 511.
32. S. Seko and N. Kawamura, J. Org. Chem., 1996, 61, 442.
33. For example, see J. Senn-Bilfinger, H. Schaefer, V. Figala, K. Klemm, G. Rainer, R. Riedel, C. Schudt and W. Simon, DE 3 240 248/1983 (Chem. Abstr., 1983, 99, 70 734k).
34. CAUTION: Dried O-methylhydroxylamine has deflagration potential. T. C. Bissot, R. W. Parry and D. H. Campbell, J. Am. Chem. Soc., 1957, 79, 796.
35. Similar regioselectivity was observed in VNS alkylation. See M. Makosza, T. Glinka and A. Kinowski, Tetrahedron, 1984, 40, 1863.
36. W. Buck, R. Sehring, G. Linden and S. Lust, DE 2 831 262/1980 (Chem. Abstr., 1980, 93, 26 083z).
37. For zinc promoted direct amination of nitropyridines, see S. Seko and K. Miyaké, Chem. Commun., 1998, 1519.
38. T. Naka, K. Nishikawa and T. Kalo, EP 459 136/1991 (Chem. Abstr., 1992, 116, 128924k).
39. B. H. Lipshutz and S. Sengupta, in Organic Reactions, ed.-in-chief L. A. Paquette, John Wiley & Sons, Inc., New York, 1992, Vol. 41, ch. 2, p. 135.
40. O. Haglund, A. A. K. M. Hai and M. Nilsson, Synthesis, 1990, 942; O. Haglund and M. Nilsson, Synthesis, 1994, 242.
41. J. B. Shoesmith and A. Mackie, J. Chem: Soc., 1928, 2334.
42. M. L. Cerrada, J. Elguero, J. de la Fuente, C. Pardo and M. Ramos, Synth. Commun., 1993, 23, 1947.
43. K.-Y. Chu and J. Griffiths, J. Chem. Soc., Perkin Trans, l, 1978, 1194.
44. M. Lemaire, A. Guy, P. Boutin and J. P. Guette, Synthesis, 1989, 761.
45. D. P. Ainsworth and H. Suschitzky, J. Chem. Soc. (Q, 1966, 111.
46. R. A. Abramovitch, R. Bartnik, M. Cooper, N._ L. Dassanayake, H.-Y. Hwang, M. N. Inbasekaran and G. Rusek, J. Org. Chem., 1982, 47, 4817.
47. H. H. Hodgson and F. W. Handley, J. Client. Sue., 1928, 162.
48. C. K. Hancock, R. A. Brown and J. P. Idoux, J. Org. Client., 1968, 33, 1947.
49. J. Ohmori, S. Sakamoto, H. Kubota, M. Shimizu-Sasamata, M. Okada, S. Kawasaki, K. Hidaka, J. Togami, T. Furuya and K. Murase, ./ Med. Chem., 1994, 37, 467.
50. M. Makosza and M. Sypniewski, Tetrahedron, 1994, 50, 4913.
51. S. Saluja, R. Zou, J. C. Drach and L. B. Townsend, J. Med. Chem., 1996, 39, 881.
52. von F. Beilstein and A. Kurbatow, Liebigs Ann. Chcm., 1879, 196, 214.
53. A. Kaiser, Chem. Ber., 1885, 18, 2942.
54. J. S. Nowick, M. Pairish, I. Q. Lee, D. L. Holmes and J. W. Ziller, J. Am. Chem. Soc., 1997, 119, 5413.
55. L. Kalb and O. Groß, Chem. Ber., 1926, 59, 727.
56. E. H. Huntress and J. V. K. Gladding, J. Am. Chem. Soc, , 1942, 64, 2644.