Synthesis of α-bromo-β-lactam via a novel catalytic Hunsdiecker like protocol[hair space][hair space]

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Dinabandhu Naskar and Sujit Roy


Abstract

While α,β-unsaturated aromatic carboxylic acids, upon treatment with NBS and catalytic group-1 metal acetates, gives β-bromostyrenes, the corresponding reactions of α,β-unsaturated aromatic amides lead to α-bromo-β-lactams.


References

  1. (a) D. Crich, in Comprehensive Organic Synthesis, eds. B. M. Trost and V. L. Steven, Pergamon: Oxford, 1991, vol. 7, pp. 723–734 Search PubMed; (b) A. Hassner and C. Stumer, Organic Synthesis Based on Name Reactions and Unnamed Reaction, Pergamon, Oxford, 1994, p. 183 Search PubMed.
  2. B. M. Trost, Angew. Chem., Int. Ed. Engl., 1995, 34, 259 CrossRef CAS.
  3. S. Chowdhury and S. Roy, J. Org. Chem., 1997, 62, 199 CrossRef CAS; Chem. Eng. News, January 27, 1997, 24 Search PubMed.
  4. Semi-empirical calculations (AM1) were performed using the program Hyperchem® 5.0 (Hypercube Inc., Ontario, Canada). Restricted Hartree-Fock calculations were carried out for singlet ground states.
  5. F. Homsi and G. Rousseau, J. Org. Chem., 1999, 64, 81 CrossRef CAS.
  6. A. Pommier and J.-M. Pons, Synthesis, 1993, 441 CrossRef CAS.
  7. J. Mulzer and M. Zippel, J. Chem. Soc., Chem. Commun., 1981, 891 RSC.
  8. D. S. Noyce and E. H. Banitt, J. Org. Chem., 1966, 4043 CAS.
  9. (a) H. E. Zaugg, Org. React. (N.Y.), 1954, 8, 305; (b) T. Imai and S. Nishida, J. Org. Chem., 1980, 45, 2355.
  10. G. Asensio, M. A. Miranda, J. Perez-Prieto, M. J. Sabater and A. Simon-Fuentes, Angew. Chem., 1990, 29, 1146.
  11. Formation of lithium salt of amide I is thermodynamically favourable N-alkylation of amides in the presence of sodium hydroxide is reported: T. Gajda and A. Zwierzak, Synthesis, 1981, 1005 Search PubMed.
  12. (a) M. A. Ogliaruso and J. F. Wolfe, Synthesis of Lactones and Lactams, John Wiley and Sons, New York, 1993 Search PubMed; (b) For a review see: R. Southgate, Contemp. Org. Synth., 1994, 1, 417 Search PubMed.
  13. (a) A. K. Bose, G. Spiegelman and M. S. Manhas, Tetrahedron Lett., 1971, 3167 CrossRef CAS; (b) F. Duran and L. Ghosez, Tetrahedron Lett., 1970, 245 CrossRef CAS.
  14. (a) B. Akermark, S. Bystrom, I. Florin, N. Johansson and I. Lagerlund, Acta Chem. Scand., Ser. B, 1974, 28, 375 Search PubMed; (b) D. Seyferth, J. M. Burlitch, H. Dertouzos, Jr. and H. D. Simmons, J. Organomet. Chem., 1967, 7, 405 CrossRef CAS.
  15. B. Quiclet-Sire, J. B. Saunier and S. Z. Zard, Tetrahedron Lett., 1996, 37, 1397 CrossRef CAS.
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