Regioselective reactions of organozinc reagents with 2,4- dichloroquinoline and 5,7-dichloropyrazolo[1,5-α]pyrimidine

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 453-457

  Shiota, Takeshi ^a   Yamamori, Teruo ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DICHLOROQUINOLINE; 5,7 DICHLOROPYRAZOLO[1,5 A]PYRIMIDINE; ANGIOTENSIN RECEPTOR ANTAGONIST; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; DRUG SYNTHESIS; METAL BINDING; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033593485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981423a     Document Type: Article

References (31)

1. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
2. (b) Kalinin, V. N. Synthesis 1992, 413.
3. (c) Mitchell, T. N. Synthesis 1992, 803.
4. (d) Hatanaka, Y.; Hiyama T. Synlett 1991, 845.
5. (e) Miyama, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
6. (f) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
7. (g) Ritter, K. Synthesis 1993, 735.
8. (a) Knochel, P. Act. Met. 1996, 191.
9. (b) Erdik, E. Tetrahedron 1987, 43, 2203.
10. (c) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445. Rieke, R. D. Science 1989, 246, 1260.
11. (c) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445. Rieke, R. D. Science 1989, 246, 1260.
12. Negishi, E. Acc. Chem. Res. 1982, 15, 340.
13. For some applications of Pd-catalyzed coupling reactions to combinatorial chemistry, see: Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
14. Biological results of these compounds will be published elsewhere.
15. (a) Kamikawa, T.; Hayashi, T. Tetrahedron Lett. 1997, 38, 7087.
16. (b) Sekiya, K.; Nakamura, E. Tetrahedron Lett. 1988, 29, 5155.
17. (a) Samalley, R. K. The Chemistry of Heterocyclic Compounds; Gurnos, J., Ed.; J. Wiley & Sons, Inc.: New York, 1977; Vol 32, Quinolines, Chapt. 3.
18. (b) Illuminati, G.; Marino, G. Atti Accad. Naz. Lincei, Cl. Sci. Fis. Mat. Nat., Rend. 1965, 38, 525.
19. Cruskie, M. P., Jr.; Zoltewicz, J. A. Abboud, K. A. J. Org. Chem. 1995, 60, 7491.
20. (a) Floch, P. L.; Carmichael, D.; Ricard, L.; Mathey, F. J. Am. Chem. Soc. 1993, 115, 10665.
21. (b) Trauner, H.; Floch, P. L.; Lefour, J.-M.; Ricard, L.; Mathey, F. Synthesis 1995, 717.
22. Osborne, A. G.; Miller, L. A. D. J. Chem. Soc., Perkin Trans. 1 1993, 181.
23. A referee pointed out a literature reference which reported the 4-selective reaction of 2,3,4,5,6-pentachloropyridine with benzylmagnesium chloride. Dua, S. S.; Gilman H. J. Organomet. Chem. 1968, 12, 299.
24. Rathke, M. W.; Yu, H. J. Org. Chem. 1972, 37, 1732.
25. (a) Marx, B.; Basch, E, H.; Freon, P. C. R. Acad. Sci., Ser. C 1967, 264, 527.
26. (b) Marx, B.; Basch, E, H.; Freon, P. C. R. Acad. Sci., Ser. C 1968, 266, 1646.
27. Kimura, E.; Shiota, T.; Koike, T.; Shiro, M.; Kodama, M. J. Am. Chem. Soc. 1990, 112, 5805.
28. Senga, K.; Novinson, T.; Wilson, H. R.; Robins, R. K. J. Med. Chem. 1981, 24, 610.
29. O'Brien, D. E.; Viejo, M.; Robins, R. K.; Simon, L. N. U.S. Patent 3,907,799, Sept 23, 1975.
30. Koller, G. Chem. Ber. 1927, 60, 8.
31. Carini, D. J.; Duncia, J. V.; Aldrich, P. E.; Chiu, A. T.; Johnson, A. L.; Pierce, M. E.; Price, W. A.; Santella III, J B.; Wells, G. J.; Wexler, R. R.; Wong, P. C.; Yoo, S.-E.; Timmermans, P. B. M. W. M. J. Med. Chem. 1991, 34, 2525.