Synthesis and reactions of N-ethynyl-heterocycles

Heterocycles

Volumn 63, Issue 6, 2004, Pages 1455-1475

  Katritzky, Alan R ^a   Jiang, Rong ^a   Singh, Sandeep K ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTRIAZOLE DERIVATIVE; HETEROCYCLIC COMPOUND;

ADDITION REACTION; CHEMICAL REACTION; CYCLOADDITION; ELIMINATION REACTION; ISOMERIZATION; POLYMERIZATION; REACTION ANALYSIS; REVIEW; SUBSTITUTION REACTION; SYNTHESIS;

EID: 2942556641     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/rev-04-575     Document Type: Review

References (56)

1. a) M. Furber, In Comprehensive Organic Functional Group Transformations; A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Eds.; Pergamon: Oxford, 1995; Vol. 1, P. 997;
2. b) J. Ficini, Tetrahedron, 1976, 32, 1449;
3. c) J. Collard-Motte and Z. Janousek, Topics in Current Chemistry, 1986, 130, 89;
4. d) C. A. Zificsak, J. A. Mulder, R. P. Hsung, C. Rameshkumar, and L. Wei, Tetrahedron, 2001, 57, 7575.
5. T. Mantani, T. Ishihara, T. Konno, and H. Yamanaka, J. Fluorine Chem., 2001, 108, 229.
6. J. Ficini and C. Barbara, Bull. Soc. Chim. Fr., 1965, 2787.
7. S. Y. Delavarenne and H. G. Viehe, Chem. Ber., 1970, 103, 1198.
8. G. Himbert, H. Nabhan, and S. Kosack, Synlett, 1991, 117.
9. H. Berger, H. Noth, and B. Wrackmeyer, J. Organomet. Chem., 1978, 145, 17.
10. R. V. Joshi, Z. Q. Xu, M. B. Ksebati, D. Kessel, T. H. Corbett, J. C. Drach, and J. Zemlicka, J. Chem. Soc., Perkin Trans. 1, 1994, 1089.
11. R. V. Joshi, D. Kessel, T. H. Corbett, and J. Zemlicka, J. Chem. Soc., Chem. Commun., 1992, 513.
12. H. J. Chou, J. P. Froehlich, and J. Pitha, Nucl. Acids. Res., 1978, 5, 691.
13. S. Phadtare and J. Zemlicka, J. Am. Chem. Soc., 1989, 111, 5925.
14. S. Hayashi, S. Phadtare, J. Zemlicka, M. Matsukura, H. Mitsuya, and S. Broder, Proc. Natl. Acad. Sci. USA, 1988, 85, 6127.
15. M. S. Paley, D. O. Frazier, H. Abeledeyem, S. P. McManus, and S. E. Zutaut, J. Am. Chem. Soc., 1992, 114, 3247.
16. Y. Okamoto and S. K. Kundu, J. Org. Chem., 1970, 35, 4250.
17. J. Pielichowski and R. Chrzaszcz, Bull. Soc. Chim. Belg., 1995, 104, 117.
18. G. Himber, H. Nabhan, and O. Gerulat, Synthesis, 1997, 293.
19. H. J. Gais, Tetrahedron Lett., 1984, 25, 273.
20. U. Lienhard, H. Fahrni, and M. Neuenschwander, Helv. Chim. Acta, 1978, 61, 1609.
21. D. Berger, P. Wihelm, and M. Neuenschwander, Helv. Chim. Acta, 1999, 82, 326.
22. J. Bloxham and C. P. Dell, Tetrahedron Lett., 1991, 32, 4051.
23. L. Wei, J. A. Mulder, H. Xiong, C. A. Zificsak, C. J. Douglas, and R. P. Hsung, Tetrahedron, 2001, 57, 459.
24. R. Buijle, A. Halleux, and H. G. Viehe, Angew. Chem., Int. Ed. Engl., 1966, 5, 584.
25. V. R. Gompper and W. Elser, Tetrahedron Lett., 1964, 1971.
26. A. G. Mal'kina, O. A. Tarasova, H. D. Verkruijsse, A. C. H. T. M. van der Kerk, L. Brandsma, and B. A. Trofimov, Recl. Trav. Chim. Pays-Bas., 1995, 114, 18.
27. H. G. Viehe and M. Reinstein, Angew. Chem., Int. Ed. Engl., 1964, 3, 506.
28. P. P. Montijn, E. Harryvan, and L. Brandsma, Recl. Trav. Chim. Pays-Bas., 1964, 83, 1211.
29. E. J. Corey and D. E. Cane, J. Org. Chem., 1970, 35, 3405.
30. J. L. Dumont, C. R. Hebd. Seances Acad. Sci., Ser. B, 1965, 261, 1710.
31. A. R. Katritzky and W. H. Ramer, J. Org. Chem., 1985, 50, 852.
32. H. Fischer, O. Podschadly, G. Roth, S. Herminghaus, S. Klewitz, J. Heck, S. Houbrechts, and T. Meyer, J. Organomet. Chem., 1997, 541, 321.
33. A. R. Katritzky, J. Wang, N. Karodia, and J. Li, J. Org. Chem., 1997, 62, 4142.
34. A. R. Katritzky, S. Zhang, and Y. Fang, Org. Lett., 2000, 2, 3789.
35. a) T. Kitamura, N. Tashi, K. Tsuda, and Y. Fujiwara, Tetrahedron Lett., 1998, 39, 3787;
36. b) T. Kitamura, N. Tashi, K. Tsuda, H. Chen, and Y. Fujiwara, Heterocycles, 2000, 52, 303.
37. A. R. Katritzky, S. K. Singh, and R. Jiang, Unpublished Results.
38. E. V. Tretyakov and S. F. Vasilevsky, Russ. Chem. Bull., 1998, 47, 1233.
39. A. Balsamo, B. Macchia, F. Macchia, and A. Rossello, Tetrahedron Lett., 1985, 26, 4141.
40. R. F. C. Brown, F. W. Eastwood, G. D. Fallon, S. C. Lee, and R. P. McGeary, Aust. J. Chem., 1994, 47, 991.
41. H. G. Viehe, Angew. Chem., Int. Ed. Engl., 1967, 6, 767.
42. a) F. Fischer, D. Berger, and M. Neuenscheander, Angew. Chem., Int. Ed. Engl., 1998, 37, 2138;
43. b) D. Berger and M. Neuenscheander, Chimia, 1995, 49, 72,
44. c) C. Bacilieri, S. Reic, and M. Neuenschwander, Helv. Chim. Acta, 2000, 83, 1182.
45. A.R. Katritzky, Ashraf A. A. Abdel-Fattah, and M. Wang, J. Org. Chem., 2002, 67, 7526.
46. M. C. Pirrung, J. Zhang, and A. T. Morehead, Tetrahedron Lett., 1994, 35, 6229.
47. R. P. Hsung, C. A. Zificsak, L. L. Wei, C. J. Douglas, H. Xiong, and J. A. Mulder, Org. Lett., 1999, 1, 1237.
48. M. L. M. Pennings and D. N. Reinhoudt, Tetrahedron Lett., 1980, 21, 1781.
49. P. A. Van Elburg, G. W. N. Honig, and D. N. Reinhoudt, Tetrahedron Lett., 1987, 28, 6397.
50. J. Bloxham and C. P. Dell, J. Chem. Soc., Perkin Trans. 1, 1993, 3055.
51. J. Balsells, J. Vazquez, A. Moyano, M. A. Pericas, and A. Riera, J. Org. Chem., 2000, 65, 7291.
52. J. Ficini and C. Barbara, Tetrahedron Lett., 1966, 6425.
53. T. Nakai, H. Setoi, and Y. Kageyama, Tetrahedron Lett., 1981, 22, 4097.
54. J. A. Mulder, R. P. Hsung, M. O. Frederick, M. R. Tracey, and C. A. Zificsak, Org. Lett., 2002, 4, 1383.
55. K. Iwamoto, S. Suzuki, E. Oishi, A. Miyashita, and T. Higashino, Heterocycles, 1996, 43, 199.
56. K. Iwamoto, E. Oishi, T. Sano, A. Tsuchiya, Y. Suzuki, T. Higashino, and A. Miyashita, Heterocycles, 1996, 45, 1551.