Annulation of dihydroimidazoles: A 1,3-dipolar cycloaddition route to pyrrolo[1,2-a]imidazoles, pyrrolidines and pyrroles

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 13, 1998, Pages 2061-2072

  Jones, Raymond C F ^a   Howard, Kevin J ^a   Nichols, John R ^b   Snaith, John S ^a  

^a OPEN UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748636515     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a802048e     Document Type: Article

References (30)

1. For examples and leading references, see: J. Rouden, J. Royer and H.-P. Husson, Tetrahedron Lett., 1989, 30, 5133;
2. R. M. Williams, W. Zhai, D. J. Aldous and S. C. Aldous, J. Org. Chem., 1992, 57, 6527;
3. L. M. Harwood and I. A. Lilley, Tetrahedron Lett., 1993, 34, 537;
4. J. A. Monn and M. J. Valli, J. Org. Chem., 1994, 59, 2773;
5. A. R. Katritzky, J. Koditz and H. Y. Lang, Tetrahedron, 1994, 50, 12 571;
6. I. Coldham, A. J. Collis, R. J. Mould and D. E. Robinson, Synthesis, 1995, 1147;
7. R. Grigg, Tetrahedron: Asymmetry, 1995, 6, 2475;
8. M. E. Kopach, A. H. Fray and A. I. Meyers, J. Am. Chem. Soc., 1996, 118, 9876;
9. Z. Ma, S. Wang, C. S. Cooper, A. K. L. Fung, J. K. Lynch, F. Plagge and D. T. W. Chu, Tetrahedron: Asymmetry, 1997, 8, 883.
10. For leading references, see: R. C. F. Jones, P. Patel, S. C. Hirst and I. Turner, Tetrahedron, 1997, 53, 11 781;
11. R. C. F. Jones, J. S. Snaith, M. W. Anderson and M. J. Smallridge, Tetrahedron, 1997, 53, 1111.
12. R. C. F. Jones and M. J. Smallridge, Tetrahedron Lett., 1988, 29, 5005;
13. R. C. F. Jones and S. C. Hirst, Tetrahedron Lett., 1989, 30, 5361, 5365.
14. R. Smith and T. Livinghouse, Tetrahedron, 1985, 41, 3559;
15. O. Tsuge, S. Kanesma and K. Matsuda, J. Org. Chem., 1986, 51, 1997.
16. For preliminary communication of part of this work, see: (a) R. C. F. Jones, J. R. Nichols and M. T. Cox, Tetrahedron Lett., 1990, 31, 2333;
17. (b) R. C. F. Jones and K. J. Howard, J. Chem. Soc., Perkin Trans. 1, 1993, 2391.
18. For example, see: I. R. Stirling, I. K. A. Freer and D. J. Robins, J. Chem. Soc., Perkin Trans. 1, 1997, 677.
19. T. F. Gallagher and J. L. Adams, Tetrahedron Lett., 1989, 30, 6599.
20. R. Schwesinger and H. Schlemper, Angew. Chem., Int. Ed. Engl., 1987, 26, 1167.
21. Single crystal X-ray analysis of the related 3-phenylpyrroloimidazoles confirms the trans relationship between the ester functions at C-5 and C-7: R. C. F. Jones, K. J. Howard and J. S. Snaith, Tetrahedron Lett., 1996, 37, 1707.
22. For example, see: G. Tóth, J. Frank, Z. Bende, L. Weber and K. Simon, J. Chem. Soc., Perkin Trans. 1, 1983, 1961;
23. O. Tsuge, S. Kanemasa and S. Takenaka, Bull. Chem. Soc. Jpn., 1985, 58, 3137;
24. H. Ardill, M. J. R. Dorrity, R. Grigg, M.-S. Leon-ling, J. F. Malone, V. Sridharan and S. Thianpatanagul, Tetrahedron, 1990, 46, 6433;
25. H. Ardill, X. L. R. Fontaine, R. Grigg, D. Henderson, J. Montgomery, V. Sridharan and S. Surendrakumar, Tetrahedron, 1990, 46, 6449.
26. R. Sustmann, Tetrahedron Lett., 1971, 2717.
27. R. C. F. Jones, K. J. Howard and J. S. Snaith, Tetrahedron Lett., 1997, 38, 1647.
28. E. Vedejs, S. Larsen and F. G. West, J. Org. Chem., 1985, 50, 2170.
29. D. D. Perrin, W. L. F. Armarego and D. R. Perrin, Purification of Laboratory Chemicals, Pergamon Press, second edition, 1980.
30. D. E. Goldberg and K. C. Patel, J. Inorg. Nucl. Chem., 1972, 34, 3583.