BF 3·OEt 2-promoted synthesis of acridines via N-aryl nitrenium-BF 3 ions generated by dissociation of 2-oxo azidoarenes in benzene

Arkivoc

Volumn 2006, Issue 12, 2006, Pages 111-120

  Fraleoni Morgera, Alessandro ^a   Zanirato, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Acridines; Arylazides; BF 3 OEt 2; Cyclo dehydration; Nitrenium ions; Reactivity

Indexed keywords

EID: 33747261537     PISSN: 14246376     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (105)

1. (a) Falvey, D. E. React. Intermediate Chem. 2004, 593.
2. (b) Abramovitch, R. A.; Miller, J.; de Souza, A. J. C.; Tetrahedron Lett. 2003, 44, 6965.
3. (c) Takeuchi, H.; Taniguchi, T.; Ueda, T. J. Chem. Soc., Perkin 2, 2000, 295.
4. (d) Falvey, D. E. Molec. Supramolec. Photochem. 2000, 6, 249.
5. (e) de Carvalho, M.; Sorrilha, A. E. P. M.; Rodrigues, J. A. R. J. Bras. Chem. Soc. 1999, 10, 415.
6. (f) McClelland, R. A.; Ahmad, A.; Dicks, A. P.; Licence, V.; J. Am. Chem. Soc. 1999, 121, 3303.
7. (g) Takeuchi, H.; Taniguchi, T.; Masuzawa, M.; Isoda, K.; J. Chem. Soc., Perkin 2, 1998, 1743.
8. (h) Doppler, T.; Schmid, H.; Hansen, H. J. Helv. Chim. Acta, 1979, 62, 304.
9. Borodkin, G. I.; Shubin, V. G. Russian J. Org. Chem. 2005, 41, 473.
10. Chan, P. Y.; Ong, S. Y.; Zhu, P.; Leung, K. H.; Phillips, D. L. J. Org. Chem. 2003, 68, 5265.
11. Novak, M.; Rajagopal, S. Adv. Phys. Org. Chem. 2001, 36, 167.
12. McIlroy, S.; Moran, R. J.; Falvey, D. E. J. Phys. Chem. A 2000, 104, 11154.
13. Ramlall, P.; McClelland, R. A. J. Chem. Soc., Perkin 2 1999, 225.
14. Srivastava, S.; Toscano, J. P.; Moran, R. J.; Falvey, D. E. J. Am. Chem. Soc. 1997, 119, 11552.
15. Robbins, R. J.; Laman, D. M.; Falvey, D. E. J. Am. Chem. Soc., 1996, 118, 8127.
16. Capitosti, S. M.; Hansen, T. P.; Brown, M. L. Org. Lett. 2003, 5, 2865.
17. Cheng, B.; McClelland, R. A. Can. J. Chem., 2001, 79, 1881.
18. Wardrop, D. J.; Zhang, W. M. Org. Lett. 2001, 3, 2353.
19. Pinney, K. G.; Mejia, M. P.; Villalobos, V. M.; Rosenquist, B. E.; Pettit, G. R.; Verdier-Pinard, P.; Hamel, E. Bioorg. Med. Chem. 2000, 8, 2417.
20. Habeeb, A. G.; Rao, P. N. P.; Knaus, E. E. J. Med. Chem. 2001, 44, 3039.
21. Schut, H. A. J.; Snyderwine, E. G. Carcinogenesis 1999, 20, 353.
22. Novak, M.; VandeWater, A. J.; Brown, A. J.; Sanzebacher, S. A.; Hunt, L. A.; Kolb, B. A.; Brooks, M. E. J. Org. Chem. 1999, 64, 6023.
23. Novak, M.; Xu, L.; Wolf, R. A. J. Am. Chem. Soc. 1998, 120, 1643.
24. Kadlubar, F. F. In DNA Adducts: Identification and Biological Significance Hemmink, K. K. A.; Shugar, D. E. G.; Kadlubar, F. F.; Segerback, D.; Bartsch, H. Eds., University Press: Oxford, 1994; pp 199-216.
25. Meier, C.; Boche, G. Tetrahedron Lett. 1990, 31, 1693.
26. Scribner, J. D.; Naimy, N. K.; Cancer Res. 1975, 35, 1416.
27. Miller, E. C.; Miller, J. A. Environ. Health Perspect., 1983, 49, 3.
28. nd Edn., Searle, C. E. Ed.; ACS Monograph 182;
29. Am. Chem. Soc.: Washington, DC, 1984; Vol. 1, pp 175-276.
30. Hoffman, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347.
31. Gassman, P. G.; Granrud, J. E. J. Am. Chem. Soc. 1984, 106, 1498.
32. Doyle, M. P. React. Intermediate Chem. 2004, 561.
33. Hodgson, D. M.; Christlieb, M.; Gras, E. Org. React. Mechanisms 2004, 209.
34. Platz, M. S. React. Intermediate Chem. 2004, 501.
35. Knight, J. G. Org. React. Mechanisms 2003, 253.
36. Fedorynski, M. Chem. Rev. 2003, 103, 1099.
37. Sydnes, L. K. Chem. Rev. 2003, 103, 1133.
38. Soderberg, B. C. G. Curr. Org. Chem. 2000, 4, 727.
39. Michalak, J.; Zhai, H. B.; Platz, M. S. J. Phys. Chem. 1996, 100, 14028.
40. Platz, M. S. Acc. Chem. Res. 1995, 28, 487.
41. Smith, P. A. S. Aryl and Heteroaryl Azides and Nitrenes In Azides and Nitrenes, Reactivity and Utility, Scriven, E. F. V. Ed., Academic: Orlando, 1984; pp 95-204.
42. Moss, R. A.; Jones, M. Carbenes, Wiley: New York, 1983.
43. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. Int. Ed. 2005, 44, 5188.
44. Scriven, E. F. V.; Turnbull, K. Chem. Rev., 1988, 88, 297.
45. Scriven E. F. V. Ed., Azides and Nitrenes, Reactivity and Utility, Academic: Orlando, 1984.
46. Abramovitch, R. A.; Kyba, E. P. Decomposition of organic azides, In The chemistry of the azido group, Patai, S. Ed., Interscience: London, 1971, pp 221-329.
47. L'Abbé, G. Chem. Rev. 1969, 69, 345.
48. We experienced no problem long handling several aryl and heteroaryl azides whose hazardous properties of some of them are under thermal estimation: Cardillo, P.; Zanirato, P. unpublished results.
49. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed., 2002, 41, 2596.
50. th Edn. Butterwoths: London, 1990; Ref 5.
51. Spagnolo, P.; Zanirato, P. Tetrahedron Lett. 1987, 28, 961.
52. Takeuchi, H.; Takano, K. J. Chem. Soc., Perkin 1 1986, 611.
53. Spagnolo, P.; Zanirato, P. J. Chem. Soc., Perkin 1 1988, 2615.
54. Zanirato, P.; Alberti, A.; Macciantelli D. unpublished results.
55. Graboyes, H.; Anderson, E. L.; Levinson, S. H.; Resnick, T. M. J. Heterocycl. Chem. 1975, 12, 1225.
56. Acheson, R. M. Acridines, Wiley: New York, 1973.
57. Acheson, R. M.; Orgel, L. E. 'Acridines', In The Chemistry of Heterocyclic Compounds Weissberger, A., Ed., Interscience: New York, 1956.
58. Albert, A. The Acridines, Arnold: London, 1966.
59. Bradsher, C. K. Chem. Rev., 1946, 38, 447.
60. Bertsch, U.; Winklhofer, K. F.; Hirschberger, T.; Bieschke, J.; Weber, P.; Hartl, F. U.; Tavan, P.; Tatzelt, J.; Kretzschmar, H. A.; Giese, A. J. Virol. 2005, 79, 7785.
61. Ippolito, A. Medicinal Chem. Rev. Online, 2004, 1, 267.
62. Auparakkitanon, S.; Noonpakdee, W.; Ralph, R. K.; Denny, W. A.; Wilairat, P. Antimicrob. Agents Chemother. 2003, 47, 3008.
63. Thale, Z.; Johnson, T.; Tenney, K.; Wenzel, P. J.; Lobkovsky, E.; Clardy, J.; Media, J.; Pietraszkiewicz, H.; Valeriote, F. A.; Crews, P. J. Org. Chem. 2002, 67, 9384.
64. Haqqani, M. T.; J. Clin. Pathol., 2001, 54, 734.
65. Ellis, M. J.; Stevens, M. F. G. J. Chem. Soc., Perkin 1 2001, 3174.
66. Stanslas, J.; Hagan, D. J.; Ellis, M. J.; Turner, C.; Carmichael, J.; Ward, W.; Hammonds, T. R.; Stevens, M. F. G. J. Med. Chem. 2000, 43, 1563.
67. Denny, W. A.; Cain, B. F.; Atwell, G. J.; Hansch, C.; Panthananickal, A.; Leo, A. J. Med. Chem. 1982, 25, 276.
68. Hegde, R.; Thimmaiah, P.; Yerigeri, M. C.; Krishnegowda, G.; Thimmaiah, K. N.; Houghton, P. J. Eur. J. Medicinal Chem. 2004, 39, 161.
69. Aly, E.-M. S. M.; El-Ella, A. D. A.; Seri, A. S. M.; Ebeid, M. Y. Egyptian J. Pharm. Sc. 2002, 43, 73.
70. Ellis, M. J. ; Stevens, M. F. G. J. Chem. Soc., Perkin 1 2001, 3180.
71. Su, T-L.; Chou, T-C. ; Kim, Y. J. ; Huang, J-T.; Ciszewska, G.; Ren, W-Y.; Otter, G. M.; Sirotnak, F. M.; Watanabe, K. A. J. Med. Chem. 1995, 38, 3226.
72. Osuna, A.; Ruiz-Perez, L. M.; Gamarro, F.; Rodriguez-Santiago, J. I.; Castanys, S.; Sharples, D.; Galy, A. M.; Giovannangeli, G.; Galy, J. P. Chemotherapy 1988, 34, 127.
73. Atwell, G. J.; Cain, B. F.; Denny, W. A. J. Med. Chem. 1977, 20, 520.
74. Sakai, K.; Anselme, J.-P. J. Org. Chem. 1972, 37, 2351.
75. Stewart, T. J.; Shepherd, D. M. J. Med. Chem. 1970, 13, 762.
76. Schwan, T. J.; Davis, C. S. J. Pharm. Sci. 1968, 57, 877.
77. (a) Ardakani, M. A.; Smalley, R. K.; Smith, R. H. J. Chem. Soc., Perkin 1 1983, 2501.
78. (b) Forster, M. O.; Judd, H. M. J. Chem. Soc. 1910, 97, 254.
79. (c) Bamberger, E.; Demuth, E. Ber. 1902, 34, 1309.
80. Dyall, L. K.; Holmes, A-L. Aust. J. Chem. 1988, 41, 1677.
81. Takada, K.; Thoe K. W.; Boulton, A. J. J. Org. Chem. 1982, 47, 4323.
82. Meisenheimer, J.; Senn, O.; Zimmermann, P. Ber. 1927, 60, 1736.
83. Thomas, A. W. Bioorg. Med. Chem. Lett. 2002, 12, 1881.
84. Smith, P. A. S.; Brown, B. B.; Putney, R. K.; Reinisch, R. F. J. Am. Chem. Soc. 1953, 75, 6335.
85. Rao, K. A. N.; Venkataraman, P. R. J. Ind. Chem. Soc. 1938, 15, 194.
86. Cledera, P.; Avendano, C.; Menendez, C. J. Tetrahedron 1998, 54, 12349.
87. Maffei, C. Gazz. Chim. It. 1955, 85, 1300.
88. Adger, B. M.; Bradbury, S.; Keating, M.; Rees, C. W.; Storr, R. C.; Williams, M. T. J. Chem. Soc., Perkin 1 1975, 31.
89. Boyer, J. H.; Straw, D. J. Am. Chem. Soc.1953, 75, 2683.
90. Dyall, L. K.; Kemp, J. E. Aust. J. Chem. 1967, 20, 1625.
91. Matsumura, K. J. Am. Chem. Soc., 1935, 57, 1535.
92. Jourdan, F. Chem. Ber. 1885, 18, 1444.
93. Similar reaction could be the formation of 9-aminoanthracene by acidic-cyclization involving the group nitrile: Bradsher, C. K.; Beavers, D. J. J. Org. Chem., 1956, 21, 1067.
94. Abramovich, R. A.; Jeyaraman, R. Nitrenium ions In Azides and Nitrenes, Reactivity and Utility, Scriven, E. F. V. Academic Press: Orlando, 1984, pp 297-357; Refs. 8 and 1c.
95. Takeuchi, H.; Takano, K. J. Chem. Soc., Chem. Commun. 1983, 447.
96. Smith, P. A. S.; Brown, B. B. J. Am. Chem. Soc., 1951, 73, 2435.
97. Leardini, R.; McNab, H.; Nanni, D.; Parsons, S.; Reed, D.; Tenan, A. G. J. Chem. Soc., Perkin 1 1998, 1833.
98. Prager, R. H.; Williams, C. M. Science Synthesis, 2005, 15, 987.
99. Koshima, H.; Kutsunai, K. Heterocycles 2002, 57, 1299.
100. Smith, J. G.; Fogg, D. J. Heterocycl. Chem. 1985, 22, 879.
101. Hicks, M. G.; Jones, G. J. Chem. Soc., Chem. Comm. 1983, 22, 1277.
102. Skonieczny, S. Heterocycles, 1977, 6, 987.
103. Adcock, B. Chem. Heterocycl. Comp. 1973, 9, 109.
104. Raulins, N. R. Chem. Heterocycl. Comp. 1973, 9, 9.
105. Allen, C. F. H.; McKee, G. H. W. Org. Synth., 1939, 6, 15.