Stepwise synthesis of tetrasubstituted hydrazines

Abstract

A new triprotected hydrazine reagent has been made and applied in alkylation/acylation reactions for stepwise synthesis of tetrasubstituted derivatives in high purity and yield.

References

1. U. Mäeorg, L. Grehn and U. Ragnarsson, Angew. Chem., 1996, 108, 2802; Angew. Chem., Int. Ed. Engl., 1996, 35, 2626.
2. E. Wünsch, Chem. Ber., 1965, 98, 797.
3. T. Hamada and O. Yonemitzu, Synthesis, 1986, 852.
4. I. Koppel, J. Koppel, F. Degerbeck, L. Grehn and U. Ragnarsson, J. Org. Chem., 1991, 56, 7172.
5. L. Grehn, K. Gunnarsson and U. Ragnarsson, Acta Chem. Scand., Ser. B, 1986, 40, 745.
6. O. Mitsunobu, Synthesis, 1981, 1; D. L. Hughes, Org. React., 1992, 42, 335.
7. U. Jensen-Korte and N. Müller, Methoden Org. Chem. (Houben-Weyl), 4th edn. 1952–1990, vol. E16a, pp. 807–815; J. Elguero, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky, C. W. Rees and K. T. Potts, Pergamon, Oxford, 1984, vol. 5, pp. 291–301; J. B. Polya, ibid., pp. 762–768.
8. H. Han and K. D. Janda, J. Am. Chem. Soc., 1996, 118, 2539.
9. A. R. Katritzky, J. Wu and S. V. Verin, Synthesis, 1995, 651.