Preparation and reactions of new zincated nitrogen-containing heterocycles

Tetrahedron

Volumn 53, Issue 21, 1997, Pages 7237-7254

  Prasad, A S Bhanu ^a   Stevenson, Thomas M ^a,b   Citineni, Janakiram Rao ^a,c   Nyzam, Valérie ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b DUPONT COMPANY   (United States)

^c OSMANIA UNIVERSITY   (India)

Author keywords

Copper(I) catalysis; Heteroarylzine halides; Palladium (O) catalysis; Zincated nucleosides

Indexed keywords

HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; THIAZOLE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030961821     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00427-4     Document Type: Article

References (68)

1. (a) Böhm, H.-J.; Klebe, G.; Kubinyi, H. Wirkstoffdesign, Spektrum Akademischer Verlag, Heidelberg 1996.
2. (b) King, F. D. (Ed.) Medicinal Chemistry: Principles and Practice, The Royal Society of Chemistry, Cambridge, 1994.
3. (c) Hansen, C.; Sammes, P. G.; Taylor, J. B. (Eds.) Comprehensive Medicinal Chemistry, Pergamon Press, Oxford, 1990.
4. (a) Newkome, G. R.; Pandler, W. W. Contemporary Heterocyclic Chemistry, Wiley, New York, 1982.
5. (b) Gilchrist, T. L. Heterocyclen-Chemie, VCH, Weinheim, 1995.
6. (a) Snieckus, V. Chem. Rev. 1990, 90, 879.
7. (b) Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron, 1993, 49, 49.
8. (c) Hocek, M. ; Masojidkova, M. ; Holy, A. Coll. Czech. Chem. Commun. 1997, 62, 136.
9. (d) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron 1993, 49, 9713.
10. (a) Majid, T. N.; Knochel, P. Tetrahedron Lett. 1990, 31, 4413.
11. (b) Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415.
12. Stevenson, T. M.; Prasad, A. S. B.; Citineni, J. R.; Knochel, P. Tetrahedron Lett. 1996, 37, 8375.
13. (a) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
14. (b) Knochel, P. Synlett 1995, 393.
15. (a) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
16. (b) Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5223.
17. (c) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
18. (d) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955.
19. (e) Rottländer, M.; Palmer, N.; Knochel, P. Synlett 1996, 573.
20. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
21. Apen, P. G.; Rasmussen, P. G. Heterocycles 1989, 29, 1325.
22. (a) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
23. (b) Cluet, F.; Handrechy, A.; Le Ber, P.; Sinay, P.; Wick, A. Synlett 1994, 912.
24. (c) Cho, Y.-M.; Johnson, F. Tetrahedron Lett. 1994, 35, 1149.
25. (d) Kubik, S.; Meissner, R. S.; Rebek, J. Tetrahedron Lett. 1994, 35, 6635.
26. (e) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236.
27. (f) Csuk, R .; von Scholz, Y. Tetrahedron 1994, 50, 10431.
28. (g) Liu, W.; Walker, J. A.; Chen, J. J., Wise, D. S.; Townsend, L. B. Tetrahedron Lett. 1996, 37, 5325.
29. (a) Arai, I.; Daves, G. D. J. Org. Chem. 1978, 43, 4110.
30. (b) Arai, I.; Daves, G. D. J. Am. Chem. Soc. 1978, 100, 287.
31. (c) Arai, I.; Hanna, R.; Daves, G. D. J. Am. Chem. Soc. 1981, 103, 7684.
32. (d) Undheim, K.; Benneche, T. Acta Chem. Scand. 1993, 47, 102.
33. (e) Hayakawa, H.; Tanaka, H.; Obi, K.; Itoh, M.; Miyasaka, T. Tetrahedron Lett. 1987, 28, 87.
34. (f) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149.
35. (g) Armstrong, R. W.; Gupta, S.; Whelihan, F. Tetrahedron Lett. 1989, 30, 2057.
36. (a) Gundersen, L.-L. Tetrahedron Lett. 1994, 35, 3155.
37. (b) Gundersen, L.-L.; Bakkestuen, A. K.; Aasen, A. J.; Øverås, H.; Rise, F. Tetrahedron 1994, 50, 9743.
38. (c) Luyten, I.; De Winter, H.; Busson, R.; Lescrinier, T..; Creuven, I.; Durant, F.; Balzarini, J.; De Clercq, E.; Herdewijn, P. Helv. Chim. Acta 1996, 79, 1462.
39. (d) Gundersen, L.-L.; Langli, G.; Rise, F. Tetrahedron Lett. 1995, 36, 1945.
40. (e) Nagatsugi, F.; Uemura, K.; Nakashima, S.; Maeda, M.; Sasaki, S. Tetrahedron Lett. 1995, 36, 421.
41. (f) Matteucci, M. D.; von Krosigk, U. Tetrahedron Lett. 1996, 37, 5057.
42. (g) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. Tetrahedron Lett. 1990, 31, 5877.
43. (h) Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324.
44. (a) Zemlicka, J. Coll. Czech. Chem. Comm. 1970, 35, 3572.
45. (b) Zemlicka, J. Holy, A. Coll. Czech. Chem. Comm. 1967, 32, 3159.
46. Robins, M. J.; Barr, P. J.; Giziewicz, J. Can. J. Chem. 1982, 60, 554.
47. Bredereck, H. Chem. Ber. 1947, 80, 401.
48. Nair, V.; Richardson, S. G. J. Org. Chem. 1980, 45, 3969.
49. Villiéras, J.; Rambaud, M. Synthesis, 1982, 924.
50. Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799.
51. Piers, E.; Nagakura, I. Synth. Commun. 1975, 5, 193.
52. Rettig, M. F.; Maitlis, P. M. Inorg. Synth. 1977, 17, 134.
53. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
54. (b) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
55. The preparation and reactivity of 6-oxocyclohexenylzinc iodide is currently being investigated and will be reported elsewhere.
56. Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393.
57. Brandsma, L. Preparative Acetylenic Chemistry, Elsevier, Amsterdam, 1971, p. 99
58. Piers, E.; Grierson, J. R.; Lau, C. K.; Nagakura, I. Can. J. Chem. 1982, 60, 210.
59. (a) Corcoran, R. C.; Bang, S. H. Tetrahedron Lett. 1990, 31, 6757.
60. (b) Bulot, J. J.; Aboujaouode, E. E.; Collignon, N. Phosphorus and Sulfur 1984, 21, 197.
61. Brandsma, L.; Verkruijsse, H. D. Preparative Polar Organometallic Chemistry, Springer-Verlag, New-York, 1987, p 172.
62. Ogilvie, K. K.; Beaucage, S. L.; Gillen, M. F. Tetrahedron Lett. 1978, 35, 3203.
63. Das, B.; Kundu, N. G. Synth. Commun. 1988, 18, 855.
64. (a) Elian, G. B.; Hitchings, G. H. J. Am. Chem. Soc. 1956, 78, 3508.
65. (b) McKenzie, T. C.; Epstein, J. W. J. Org. Chem. 1982, 47, 4881.
66. Robins, R. K.; Godefroi, E. P.; Taylor, E. C.; Lewis, L. R.; Jackson, A. J. Am. Chem. Soc. 1961, 83, 2574.
67. Fleischner, A. M.; Cross, J. M.; Segelman, A. B.; Van Es, T. J. Pharm. Sci. 1977, 66, 1206.
68. El Borai, M.; Moustafa, A. H.; Anwarn, M.; AbdelHay, F. I. Pol. J. Chem. 1981, 55, 1659.