Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles

Journal of Organic Chemistry

Volumn 71, Issue 9, 2006, Pages 3375-3380

  Katritzky, Alan R ^a   Cai, Chunming ^a   Singh, Sandeep K ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDOYLBENZOTRIAZOLES; MICROWAVE REACTIONS; POLYSUBSTITUTED AMIDINES;

AMINES; IRRADIATION; MICROWAVES; SUBSTITUTION REACTIONS;

NITROGEN COMPOUNDS;

AMIDINE; AMINE; BENZOTRIAZOLE DERIVATIVE; IMIDOYLBENZOTRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HEATING; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

AMIDINES; MICROWAVES; TRIAZOLES;

EID: 33646264574     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052443x     Document Type: Article

References (76)

1. (a) Hodson, H. F.; Randall, A. W. U.S. Patent 3728389, 1973; Chem. Abstr. 1973, 79, 18445.
2. (b) Marchenko, N. B.; Granik, V. G.; Glushkov, R. G.; Budanova, L. I.; Kuzovkin, V. A.; Parshin, V. A.; Al'tshuler, R. A. Khim.-Farm. Zh. 1976, 10, 46;
3. Chem. Abstr. 1977, 86, 89294.
4. (c) Caughey, G. H.; Raymond, W. W.; Bacci, E.; Lombardy, R. J.; Tidwell, R. R. Chem. Abstr. 1993, 118, 182795.
5. (d) Kitamura, S.; Fukushi, I.; Miyawaki, T.; Kawamura, M.; Terashita, E.; Naka, T.; Chem. Pharm. Bull. 2001, 49, 268.
6. (e) Som, P.; Werbovetz, K.; Stepnens, C.; Boykin, D. Chem. Abstr. 2004, 139980.
7. (f) Gautier, J. A.; Miocque, M.; Farnoux, C. C. In The Chemistry of Amidines and Imidates; Patai, S., Ed.; John Wiley & Sons: London, 1975; p 283.
8. (g) Granik, V. G. Usp. Khim. 1983, 52, 669;
9. Chem. Abstr. 1983, 99, 405265.
10. (a) Dunn, P. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 5, p 741.
11. (b) Robev, S. Dokl. Bolg. Akad. Nauk. 1983, 36, 233.
12. (c) Singh, B.; Collins, J. C. J. Chem. Soc. D 1971, 10, 498.
13. (d) Oxley, P.; Short, W. F. J. Chem. Soc., Abstr. 1949, 449.
14. (e) Clement, B.; Kaempchen, T. Chem. Ber. 1986, 119, 1101.
15. (f) Tsatsas, G.; Delaby, R.; Quevauviller, A.; Damiens, R.; Blanpin, O. Ann. Pharm. Fr. 1956, 4, 607.
16. (g) Paul, H.; Weise, A.; Dettmer, R. Chem. Ber. 1965, 98, 1450.
17. (h) Tsatsas, G.; Delaby, R. Ann. Pharm. Fr. 1956, 4, 621.
18. (i) Weintraub, L.; Oles, S. R.; Kalish, N. J. Org. Chem. 1968, 33, 1679.
19. (j) Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
20. (k) Oxley, P.; Peak, D. A.; Short, W. F. J. Chem. Soc., Abstr. 1948, 1618.
21. (a) Kantlehner, W. K.; Mergen, W. W. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 5, pp 653-657.
22. (b) Boehme, H.; Ahrens, K. H.; Drechsler, H. J.; Rumbaur G. Z. Naturforsch, B: Chem. Sci. 1978, 33, 636;
23. Chem. Abstr. 1978, 89, 163218.
24. (a) Katritzky, A. R.; Rachwal, S.; Offerman, R. J.; Zbiginew, N.; Yagoub, A. K.; Zhang, Y. Chem. Ber. 1990, 123, 1545.
25. (b) Katritzky, A. R.; Stevens, C. V.; Zhang, G.-F.; Jiang, J. Heterocycles 1995, 40, 231.
26. (c) Katritzky, A. R.; Yang, B.; Abonia, R.; Insuasty, B. J. Chem. Res., Synop. 1996, 540.
27. (d) Katritzky, A. R.; Hayden, A. E.; Kirichenko, K.; Pelphrey, P.; Ji, Y. J. Org. Chem. 2004, 69, 5108.
28. (e) Katritzky, A. R.; Donkor, A.; Fang, Y. J. Org. Chem. 2001, 66, 4041.
29. (a) Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, 2002.
30. (b) Ferreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
31. (c) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
32. (d) Caddick, S. Tetrahedron 1995, 51, 10403
33. (e) Fini, A.; Breccia, A. Pure Appl. Chem. 1999, 71, 573.
34. (f) Katritzky, A. R.; Singh, S. K. ARKIVOC 2003, xiii, 68.
35. (g) Katritzky, A. R.; Cai, C.; Suzuki, K.; Singh, S. K. J. Org. Chem. 2004, 69, 811.
36. (a) Varma, R. S. Green Chem. 1999, 1, 43.
37. (b) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
38. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Synthesis 2003, 2795.
39. Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
40. Wang, X.; Zhang, Y. Tetrahedron 2003, 59, 4201.
41. Katritzky, A. R.; Suzuki, K.; Singh, S. K.; He, H.-Y. J. Org. Chem. 2003, 68, 5720.
42. Katritzky, A. R.; Shestopalov, A. A.; Suzvki, K. ARKIVOC 2005, vii, 36.
43. Walter, R.; Manfred, S. Chem. Ber. 1965, 98, 3142.
44. Minato, H.; Takeda, K.; Miura, T.; Kobayashi, M. Chem. Lett. 1977, 9, 1095.
45. Jart, A. Acta Polytech. Scand., Chem. Ind. Metall. Ser. 1965, 44, 54.
46. Birch, D. J.; Guildford, A. J.; Tometzki, M. A.; Turner, R. W. J. Org. Chem. 1982, 47, 3547.
47. Cossy, J.; Pale-Grosdemange, C. Tetrahedron Lett. 1989, 30, 2771.
48. Chiriac, C. I. Rev. Roum. Chim. 1985, 30, 799.
49. Badr, M. Z. A.; Aly, M. M.; Abdel-Latif, F. F. J Org. Chem. 1979, 44, 3244.
50. Chiriac, C. I. Rev. Roum. Chim. 1980, 23, 403.
51. Suzuki, H.; Tsuji, J.; Hiroi, Y.; Sato, N.; Osuka, A. Chem. Lett. 1983, 4, 449.
52. Dernier, O. C.; King, J. J. Org. Chem. 1943, 8, 168.
53. Lee, C. K.; Yu, J. S.; Ji, Y. R. J. Heterocycl. Chem. 2002, 39, 1219.
54. Friedman, L. B.; Hartsuck, J. A.; Lipscomb, W. N. J. Am. Chem. Soc. 1966, 88, 3440.
55. Yeung, J. M.; Knaus, E. E. Eur. J. Med. Chem. 1986, 21, 181.
56. Ballini, R.; Bosica, G.; Fiorini, D. Tetrahedron 2003, 59, 1143.
57. Joseph, S. P.; Dhar, D. N. Tetrahedron 1986, 42, 5979.
58. Culvert, D. J.; O'Connor, C. J. Aust. J. Chem. 1979, 32, 337.
59. Kametani, T.; Takano, S.; Umezawa, O.; Agui, H.; Kanno, K.; Konno, Y.; Sato, F.; Nemoto, H.; Yamaki, K.; Ueno, H. Yakugaku Zasshi 1966, 86, 8328.
60. Pigulla, J.; Roeder, E. Arch. Pharm. (Weinheim, Ger.) 1979, 312, 12.
61. Armesto, D.; Horspool, W. M.; Perez-Ossorio, R.; Ramos, A. J. Org. Chem. 1987, 52, 3378.
62. Yamaye, M.; Cho, N.; Teteizumi, K.; Samura, T.; Kito, T.; Ichiki, T. Kyushu Kyoritsu Daigaku Kogakubu Kenkyu Hokoku 2003, 27, 37.
63. Kawashima, E.; Takada, T.; Tabei, K.; Kato, T. J. Heterocycl. Chem. 1985, 22, 1409.
64. Redmore, D.; Dhawan, B. Phosphorus Sulfur Relat. Elem. 1983, 16, 233.
65. Manimaran, T.; Thiruvengadam, T. K.; Ramakrishnan, V. T. Synthesis 1975, 11, 739.
66. Tani, J.; Oine, T.; Inoue, I. Synthesis 1975, 11, 714.
67. (a) Katritzky, A. R.; Monteux, D. A.; Tymoshenko, D. O. Org. Lett. 1999, 1, 577.
68. (b) Katritzky, A. R.; Button, M. A. C.; Busont, S. J. Org. Chem. 2001, 66, 2865.
69. (c) Katritzky, A. R.; Huang, T. B.; Voronkov, M. V. J. Org. Chem. 2001, 66, 1043.
70. Thiebaut, S.; Gerardin-Charbonnier, C.; Selve, C. Tetrahedron 1999, 55, 1329.
71. Sen, M.; Ray, J. N. J. Chem Soc., Abstr. 1926, 646.
72. Ta-Shma, R.; Rappoport, Z. J. Am. Chem. Soc. 1977, 99, 1845.
73. Oxley, P.; Short, W. F. J. Chem. Soc., Abstr. 1948, 1514.
74. Barluenga, J.; Aznar, F.; Liz, R.; Rodes, R. J. Chem. Soc., Perkin Trans. 1 1980, 12, 2732.
75. Strain, H. T. J. Am. Chem. Soc. 1928, 50, 2218.
76. Shah, R. C. J. Univ. Bombay, Sci. 1936, 5 (Part 2), 62.