On the utility of the azido transfer protocol: Synthesis of 2- And 5-azido N-methylimidazoles, 1,3-thiazoles and N-methylpyrazole and their conversion to triazole - azole bisheteroaryls

Organic and Biomolecular Chemistry

Volumn 3, Issue 8, 2005, Pages 1508-1513

  Zanirato, Paolo ^a   Cerini, Stefano ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CHARGE TRANSFER; COMPLEXATION; ION EXCHANGE; MOLECULAR STRUCTURE; PHOTOCHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

AZIDE; HETEROARYLLITHIUMS; HISHETEROARYLS; KINETIC STUDIES;

ORGANIC COMPOUNDS;

EID: 18444393047     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500634a     Document Type: Article

References (73)

1. (a) E. F. V. Scriven and K. Turnbull. Chem. Rev., 1958, 88, 298-360;
2. (b) P. A. S. Smith, Aryl and Heteroaryl Azides and Nitrenes, in Azides and Nitrenes, Reactivity and Utility, ed. E. F. V. Scriven, Academic Press, Orlando, 1984, pp. 95-204.
3. P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1996, 963-64;
4. S. Gronowitz and P. Zanirato, J. Chem. Soc., Perkin Trans. 2, 1994, 1815-1819 and refs therein.
5. E. Foresti, M. T. Di Gioia, D. Nanni and P. Zanirato, Gazz. Chim. Ital., 1995, 125, 151-161 and refs therein.
6. D. Spinelli and P. Zanirato. J. Chem. Soc., Perkin Trans. 2, 1993. 1129-1133.
7. F. Valenti and P. Zanirato, J. Chem. Soc., Perkin Trans. 2, 1999, 623-628;
8. P. Zanirato, Gazz. Chim. Ital., 1997, 127, 339-342.
9. A. Degl'Innocenti, M. Funicello. P. Scafato, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1996, 2561-2563;
10. A. Degl'Innocenti, M. Funicello, P. Scafato, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1995, 2141-2145;
11. M.Tosclli. P. Spagnolo and P. Zanirato, Gazz. Chim. Ital., 1989, 119, 411-413;.
12. S. Businelli, E. Di Martino and P. Zanirato, ARKIVOC. 2001, 1, 1027-1035;
13. P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1991, 1, 2789-2796.
14. For short reviews on this topic see: (a) M. Funicello, P. Spagnolo and P. Zanirato, Acta Chem. Scand., 1993, 47, 231-243;
15. (b) W. Dehaen and J. Becher, Acta Chem. Scand., 1993, 47, 244-254.
16. S. Gronowitz, C. Westerlund and A.-B. Hornfeldt, Acta Chem. Scand. Ser. B, 1975, 29, 224-232;
17. B. J. Barnes, P. J. Newcombe and R. K. Norris. Aust. J. Chem., 1983, 36, 963-976;
18. The chemistry of the azido group, ed. S. Patai, Interscience, NY, 1971, pp. 115-119.
19. (a) R. Granados, M. Rull and J. Vilarrasa, J. Heterocycl. Chem., 1976, 13, 281-284;
20. (b) R. Faure, J. P. Galy, E. J. Vincent and J. Elguero, J. Heterocycl. Chem., 1977, 14, 1299-1304;
21. (c) E. Alcade, J. de Mendoza and J. Elguero, J. Heterocycl. Chem., 1974, 11, 921-928.
22. (a) J. Elguero, R. Faure, J. P. Galy, E. J. Vincent, D. Mathieu and R. Phan Tan Luu, An. Quim., Ser. C, 1980, 76, 211-221;
23. (b) R. Faure, J. P. Galy, E. J. Vincent and J. Elguero, Can. J. Chem., 1978, 56, 46-55;
24. (c) M. Rull and J. Vilarrasa, J. Heterocycl. Chem., 1977, 14, 33-36.
25. E. Cubero, M. Orozco and F. J. Luque, J. Org. Chem., 1998, 63. 2354-2356;
26. E. Cubero, M. Orozco and F. J. Luque, J. Am. Chem. Soc., 1998, 120, 4723-4731 and refs cited therein.
27. T. A. Gadosy and R. A. McClelland, J. Am. Chem. Soc., 1999, 121, 1459-1465;
28. J. Becher, K. Brondum, N. Krake, K. Pluta, O. Simonsen, P. Molina and M. Begtrup, J. Chem. Soc., Chem. Commun., 1988, 121, 541-542.
29. D. L. Boger, S. N. Weinreb, Hetero Diels-Alder methodology in organic synthesis, in Organic Chemistry, ed. H. H. Wasserman, Academic Press, London, 1987, vol. 47.
30. J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Amsterdam, 2002;
31. B. J. Wakefield, Organollthiam Method, Academic Press, London, 1988.
32. M. S. R. C. Murty and H. Sugiyama, Biol. Pharm. Bull., 2004, 27, 468-474;
33. D. W. Bates and T. D. Yu, Drugs Today, 2003, 39, 801-813;
34. J. Zhong, Nat. Prod. Rep., 2003, 20, 584-605;
35. S. L. Kelly, D. C. Lamb and D. E. Kelly, Life Sci., 1999, 303, 157-172;
36. S. M. Benedetti and M. Bani, Drug Metab. Rev., 1999, 31, 665-717;
37. D. Sengupta and M. T. Nugyen, Tetrahedron, 1997, 53, 9647-9656.
38. (a) S. Ohta, N. Tsuno, S. Nakamura, N. Taguchi, M. Yamashita, I. Kawasaki and M. Fujieda, Heterocycles, 2000, 53. 1939-1955;
39. (b) D. Wild and A. Dirr. Mutagenesis, 1989, 4, 446-452.
40. On the bio-activity of triazole bishetcroaryl see: N. D. P. Cosford, L. R. Tehrani. J. R. Roppe, N. D. Smith and P. Prasit, PCT Int. Appl., 2003, 55 pp Application, WO 2002-US41720 2002 1213,
41. Chem. Abstr., 2003,139, 69268.
42. P. Jutzi and W. Sacriß, Chem. Ber., 1973, 106, 2815-2824;
43. S. Barcza USP, Appl. 72/1974 226249
44. (Chem. Abstr,. 1974, 80, 82971);
45. F. H. Pinkerton and S. F. Thames, J. Orgnomet. Che., 1972, 38, 29-36;
46. for a review on the topic see: B. Iddon and R. I. Ngochindo. Heterocycles, 1994, 38, 2487-2568.
47. A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici and P. Pedrini, J. Org. Chem., 1988, 53, 1748-1761;
48. A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici und P. Pedrini, Synthesis, 1987. 53, 998-1001;
49. A. Medici, P. Pedrini and A. Dondoni, J. Chem. Soc., Chem. Commun., 1981, 53, 655-656;
50. for a review on the topic see: B. Iddon, Heterocycles, 1995, 41, 533-593.
51. H. Chikashita, I. Megumi, K. Ori and K. Ito, Bull. Chem. Soc. Jpn., 1988, 61, 3637-3648;
52. H. Gilman and J. A. Bed, J. Am. Chem. Soc., 1949, 71, 2328-2331.
53. P. W. Alley and D. A. Shirley, J. Am. Chem. Soc., 1958, 80, 6271-6274;
54. for a review on the topic see: M. R. Grimmett and B. Iddon, Heterocycles, 1994, 37, 2087-2147.
55. P. Molina, P. M. Fresneda and S. Garciazafra, Tetrahedron Lett., 1996, 37, 9353-9356;
56. G. Shapiro and B. Gomez-Lor, Heterocycles, 1995, 41, 215-218;
57. A. R. Katritzky, J. J. Slawinski, F. Brunner and S. Guron, J. Chem. Soc., Perkin Trans. 1, 1989, 41, 1139-1145.
58. A. Dondoni, A. R. Mastellari, A. Mudici, E. Negrini and P. Pedrini, Synthesis, 1986, 757-759.
59. H. C. Beyerman, P. H. Berben and J. S. Bontekoe, Recl. Trav. Chim. Pays-Bas, 1954, 73, 325-332.
60. R. Faure, E. J. Vincent and A. J. Elguero, Heterocycles, 1987, 26, 333-336.
61. N. Kobayashi, M. Nakada. T. Mikitoshi, E. Tsuchida, H. Matsuda, H. Nakanishi and M. Kato, Polym. Lett., 1986, 24, 215-218;
62. H. Oda, M. Sato, Y. Morizawa, K. Oshima and H. Nosaki, Tetrahedron Lett., 1983, 24, 2877-2880.
63. F. Benedini, F. Ferrario and A. Sala, Magn. Resun. Chem., 1992, 30. 1137-1140;
64. J.-L. M. Abboud, G. Boyer, J. Elguero, P. Cahildo and R. M. Claramunt, Spectrochim. Acta, 1991, 47A, 785-790;
65. E. P. Papadopolulosand U. Hollestein, Org. Magn. Rexon., 1982, 19, 188-191.
66. S. Athmani, A. Bruce and B. Iddon, J. Chem. Soc., Perkin Trans. 1. 1992, 215-219.
67. T. L. Gilchrist, Heterocyclic Chemistry, Longman, Essex, 3rd edn., 1997, p. 295.
68. Spartan '04, Wavefunction Inc., Irvine CA;
69. W. J. Here. A Guide to Molecular Mechanics and Quantum Chemical Calculations, Wave-function, Irvine, 2003.
70. H. R. Matthews and H. Rapoport, J. Am. Chem. Soc., 1973, 95, 2297-2303.
71. W. Von E. Doering and C. H. DePuy, J. Am. Chem. Soc., 1953, 75, 5955-5957.
72. V. Ya. Pochinok and L. F. Avramenko, Ukr. Khim. Zh., 1962, 28. 511-517;
73. V. Ya. Pochinok and L. F. Avramenko, Chem. Abstr. 1963, 58, 14457.