Skip to main content
Log in

3-Halohydantoins as halolactonization reagents

  • Communications
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

By the reaction of 15 with 3-halohydantoins (4–14) in N,N-dimethylformamide, which were prepared from corresponding hydantoins, 3-bromo-5,5-dimethylhydantoin was found to be the most convenient reagent for halolactonization reaction.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. House, H.O.,Modern Synthetic Reactions 2nd ed., W.A. Benjamin Inc., Meleno Park, California, 441 pp. (1972).

    Google Scholar 

  2. Dowle, M.D. and Davies, D.I., Synthesis and Synthetic Utility of halolactones.Chem. Soc. Rev.,8, 171(1979) and references cited therein.

    Article  CAS  Google Scholar 

  3. a) Bougault, M.J., Action De L'acide Hypoiodeux Naissant Sur Les Acides Non Satures. Lactones iodees.Ann. Chim. Phys. 14, 145(1908) and references cited therein. b)idem Bougault, M.J., Action De L'acide Hypoiodeux Naissant Sur Les Acides Non Satures.ibid. Ann. Chim. Phys.,15, 296(1908).

    Google Scholar 

  4. a) Corey, E.J. and Hase, T., Studies on the Total Synthesis of Rifamycin. Highly Stereoselective Synthesis of Intermediates for Construction of the C(15) to C(29) chain.Tetra. Lett.,1979, 335. b) Terashima, S. and Jew, S., Asymmetric Halolactonization Reaction: A Highly Efficient Synthesis of Optically Active α-Hydroxy Acids from α,β-Unsaturated acids.Tetra. Lett.,1977, 1005. c) Jew, S., Terashima, S., and Koga, K., Asymmetric Halolactonization-Asymmetric Synthesis of Optically active α,α-I' Disubstituted-α-Hydroxy Acids from α,β-Un saturated Acids by the use of Halolactonization Reaction I.Tetrahedron,35, 2337 (1979). d) Cambie, R.C., Hayward, R.C., Roberts, J.L., Rutledge, P.S., lodolactonizations using Thallium (I) Carboxylates.J. Chem. Soc. Perkin I,1974, 1864. e) Bartlett, P.A. and Myerson, J., Highly Stereoselective Synthesis (+)-α-Multistriatin.J. Org. Chem.,44, 1625(1979).

    Google Scholar 

  5. Nicolaou, K.C., Seitz, S.P., Sipio, W.J., and Blount, J.F., Phenylseleno-and Phenylsulfenolactonizations. Two Highly Efficient and Syntheti Useful Cyclization Procedures.J. Am. Chem. Soc.,101, 3884(1979) and references cited therein.

    Article  CAS  Google Scholar 

  6. Cook, C., Cho, Y., Jew, S., and Suh, Y., Studies on Novel Haloactonization Using N-Haloimides under Non-aqueous Media(l).Seoul Uni. J. Pharm. Sci.,4, 109(1979).

    CAS  Google Scholar 

  7. Cook, C., and Kang, E., Novel Bromolactonization Using N-Bromophthalimide.Arch. Pharm. Res.,4, 137(1981).

    Article  CAS  Google Scholar 

  8. a) Oakes, V., Rydon, H.N., and Undheim, K., Polyazanaphthalenes. part VII. Some Derivative of Quinazoline and 1,3,5-Triazanaphthalene.J. Chem. Soc.,1962, 4678. b) Corral, R.A., and Orazi, O.O., Oxidation of Secondary Aromatic Alcohols with N-Bromoamides.Chem. Comm.,1965, 5.

  9. Pizey, S.S.,Synthetic Reagents, vol. I. John Wiely and Sons Inc., New York, 4pp. (1974) and references cited therein.

    Google Scholar 

  10. Vogel, A.I.,Practical Organic Chemistry, 3rd ed., Longmans, Green and Co. Ltd., London, 926pp. (1956).

    Google Scholar 

  11. van Tamelen, E.E., and Shamma, M., Assignment of the Olefinic Position in Unsaturated Acids by Means of the Iodolactonization Reaction.J. Am. Chem. Soc.,76, 2315(1954).

    Article  Google Scholar 

  12. All new compounds give IR, NMR, and/or mass spectral in complete accord with the desired structures.

  13. a) Ishii, Y., Ito, Y., and Kato, S., Synthesis of Hydantoin Derivatives and Halogenation of N-Halohydantoin.Kogyo Kagaku Zasshi. 61, 1254 (1958). b) Orazi, O.O., and Meseri, J., Halogenation with 3-Bromo-5,5-Dimethylhydantoin.Anales. Assoc. Quim. Argen.,37, 192(1949). c) Corral, R.A. and Orazi, O.O., N-Iodohydantoins.ibid.,44, 11(1956). d) Orazi, O.O., Fondovila, M.E., and Corral, R.A., Bromoderivatives of 5, 5-Disubstituted Hydantoins.ibid.,40, 109(1952). e) Waugh, T.D., and Waugh, R.C., N-Brominated Imides and Hydantoins. U.S. pat. 2, 971, 960(1961).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cook, Ch., Jew, Ss. & Chung, Ys. 3-Halohydantoins as halolactonization reagents. Arch. Pharm. Res. 5, 103–106 (1982). https://doi.org/10.1007/BF02856415

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02856415

Keywords

Navigation