Cobalt-mediated cyclotrimerisation of bis-alkynes and cyanamides

Chemical Communications

Volumn , Issue 21, 2004, Pages 2394-2395

  Boñaga, Llorente V R ^a   Zhang, Han Cheng ^a   Maryanoff, Bruce E ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPYRIDINE; ALKYNE; COBALT; CYANAMIDE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CYCLOADDITION; CYCLOTRIMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 9444249345     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b410012c     Document Type: Article

References (24)

1. M. Malacria, C. Aubert and J. L. Renaud, in Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, ed. M. Lautens and B. M. Trost, Georg Thieme Verlag: Stuttgart, 2001, vol 1, pp. 439-530; M. E. Welker, Curr. Org. Chem., 2001, 5, 785-807.
2. M. Malacria, C. Aubert and J. L. Renaud, in Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, ed. M. Lautens and B. M. Trost, Georg Thieme Verlag: Stuttgart, 2001, vol 1, pp. 439-530; M. E. Welker, Curr. Org. Chem., 2001, 5, 785-807.
3. (a) J. A. Varela and C. Saa, Chem. Rev., 2003, 103, 3787-3801;
4. (b) D. B. Grotjahn, in Comprehensive Organometallic Chemistry II, ed. L. S. Hegedus, E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, pp. 741-770;
5. (c) N. E. Schore, in Comprehensive Organometallic Chemistry II, ed. L. S. Hegedus, E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, pp. 703.
6. See also: (d) S. E. Gibson and A. Stevenazzi, Angew. Chem. Int. Ed., 2003, 42, 1800-1810.
7. For recent examples, see: (a) Y. Yamamoto, J. Ishii, H. Nishiyama and K. Itoh, J. Am. Chem. Soc., 2004, 126, 3712-3713;
8. (b) G. Chouraqui, M. Petit, C. Aubert and M. Malacria, Org. Lett, 2004, 6, 1519-1521;
9. (c) L. Hong and H. Butenschön, Chem. Commun., 2002, 23, 2852-2853;
10. (d) S. Saito and Y. Yamamoto, Chem. Rev., 2000, 100, 2901-2915.
11. (a) A. F. Moretto, H.-C. Zhang and B. E. Maryanoff, J. Am. Chem. Soc., 2001, 123, 3157-3158 [correction: J. Am. Chem. Soc., 2001, 124, 6792];
12. (a) A. F. Moretto, H.-C. Zhang and B. E. Maryanoff, J. Am. Chem. Soc., 2001, 123, 3157-3158 [correction: J. Am. Chem. Soc., 2001, 124, 6792];
13. (b) L. V. R. Boñaga, H.-C. Zhang, D. A. Gauthier, I. Reddy and B. E. Maryanoff, Org. Lett., 2003, 5, 4537-4540.
14. H. Bönnemann and W. Brijoux, Adv. Heterocycl. Chem., 1990, 48, 177-222; H. Bönnemann and W. Brijoux, Aspects Homogen. Catal., 1984, 5, 75-196; H. Bönnemann, W. Brijoux, R. Brinkmann and W. Meurers, Helv. Chim. Acta, 1984, 67, 1616-1624.
15. H. Bönnemann and W. Brijoux, Adv. Heterocycl. Chem., 1990, 48, 177-222; H. Bönnemann and W. Brijoux, Aspects Homogen. Catal., 1984, 5, 75-196; H. Bönnemann, W. Brijoux, R. Brinkmann and W. Meurers, Helv. Chim. Acta, 1984, 67, 1616-1624.
16. H. Bönnemann and W. Brijoux, Adv. Heterocycl. Chem., 1990, 48, 177-222; H. Bönnemann and W. Brijoux, Aspects Homogen. Catal., 1984, 5, 75-196; H. Bönnemann, W. Brijoux, R. Brinkmann and W. Meurers, Helv. Chim. Acta, 1984, 67, 1616-1624.
17. B. Heller, B. Sundermann, H. Buschmann, H.-J. Drexler, J. You, U. Holzgrabe, E. Heller and G. Oehme, J. Org. Chem., 2002, 67, 4414-4422; B. Heller, J. Reihsig, W. Schulz and G. Oehme, Appl. Organometal Chem., 1993, 7, 641-646 (Cp = cyclopentadienide; cod = 1,5-cyclooctadiene).
18. B. Heller, B. Sundermann, H. Buschmann, H.-J. Drexler, J. You, U. Holzgrabe, E. Heller and G. Oehme, J. Org. Chem., 2002, 67, 4414-4422; B. Heller, J. Reihsig, W. Schulz and G. Oehme, Appl. Organometal Chem., 1993, 7, 641-646 (Cp = cyclopentadienide; cod = 1,5-cyclooctadiene).
19. K. P. C. Vollhardt and A. Naiman, U.S. Patent 4,328,343 (1982) [Chem. Abstr. 90:186806 (1978)].
20. Aminopyridines, which are important as pharmaceutical agents, ligands in inorganic/organometallic chemistry, and fluorescent dyes, are typically prepared by substituting halogenated pyridines. For a leading reference, see: S. Thomas, S. Roberts, L. Pasumansky, S. Gamsey and B. Singaram, Org. Lett., 2003, 5, 3867-3870.
21. Structures were confirmed by 2D-NMR experiments (COSY, NOESY, HMQC, HMBC). See Electronic Supporting Information.
22. R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989.
23. -1.
24. -1.