Formation of Polysubstituted Pyridin-2-one Derivatives by Michael Addition of 3-Oxobutanamide to α,β-Ethylenic Ketones and Amides

(Note: The full text of this document is currently only available in the PDF Version )

Conor N. O$rsquoCallaghan, T. Brian H. McMurry, John E. O$rsquoBrien, Sylvia M. Draper and Fiona K. Gormley


Abstract

Reaction of 3-oxobutanamide with 4-phenylbut-3-en-2-one and with 3-aryl-2-cyanoprop-2-enamides and related compounds affords new di-, tetra- and hexa-hydropyridin-2-one derivatives, the degree of unsaturation of the product depending on the experimental conditions.


References

  1. (a) D. W. Robertson, E. E. Beedle, J. K. Swartzendruber, N. D. Jones, T. K. Elzey, R. F. Kauffman, H. Wilson and J. S. Hayes, J. Med. Chem., 1986, 29, 635 CrossRef CAS; (b) M. D. Taylor, I. Sircar and R. P. Steffen, Annu. Rep. Med. Chem., 1987, 22, 87 Search PubMed; (c) P. Dorigo, R. M. Gaion, P. Belluco, D. Fraccerollo, I. Maragno, G. Bombieri, F. Benetollo, L. Mosti and F. Orsini, J. Med. Chem., 1993, 36, 2475 CrossRef CAS.
  2. J. S. Wai, T. M. Williams, D. L. Bamberger, T. E. Fisher, J. M. Hoffman, R. J. Hudcosky, S. C. MacTough, C. S. Rooney, W. S. Saari, C. M. Thomas, M. E. Goldman, J. A. O'Brien, E. A. Emini, J. H. Numberg, J. C. Quintero, W. A. Schlief and P. S. Anderson, J. Med. Chem., 1993, 36, 249 CrossRef CAS.
  3. V. Dollé, E. Fan, C. H. Ngugen, A.-M. Aubertin, A. Kim, M. L. Andreola, G. Jamieson, L. Tarrago-Litvak and E. Bisagui, J. Med. Chem., 1995, 38, 4679 CrossRef CAS.
  4. Z. Bomika, M. B. Andaburskaya, J. Pelcers and G. Duburs, Khim. Geterosikl. Soedin., 1975, 1108 (Chem. Abstr., 1975, 83, 193035) Search PubMed.
  5. Z. Bomika, G. Dubur, A. Krauze and E. Liepins, Khim. Geterosikl. Soedin., 1979, 1377 (Chem. Abstr., 1980, 92, 94201) Search PubMed.
  6. M. M. Al-Arab, J. Heterocycl. Chem., 1990, 27, 523 CAS.
  7. C. N. O'Callaghan, T. B. H. McMurry, C. J. Cardin and D. J. Wilcock, J. Chem. Soc., Perkin Trans. 1, 1993, 2749 Search PubMed.
  8. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467 CrossRef.
  9. G. M. Sheldrick, SHELXL 93, Program for Crystal Structure Refinement, University of Göttingen, Göttingen, 1993.
Click here to see how this site uses Cookies. View our privacy policy here.