Simple Preparation of N-Benzyl-β-aminohydroxamic Acids by 1,3-Dipolar Cycloaddition­ of Nitrones

Carine Chevrier; Albert Defoin

doi:10.1055/s-2003-39412

PAPER

Simple Preparation of N-Benzyl-β-aminohydroxamic Acids by 1,3-Dipolar Cycloaddition of Nitrones

Carine Chevrier, Albert Defoin*
Laboratoire de Chimie Organique et Bioorganique UMR 7015, Ecole Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace., 3, rue Alfred Werner, 68093 Mulhouse Cédex, France
Fax: +33(3)89336875; e-Mail: A.Defoin@uha.fr;

Abstract

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Abstract

β-Aminohydroxamic acids 6a-d are prepared in 4 steps and 30-45% overall yield from nitrones 1a-d by 1,3-dipolar cycloaddition with phenyl vinyl ether, N-benzylation, thermal rearrangement, and nucleophilic substitution of the formed phenyl ester with hydroxylamine.

Key words

β-amino acids - hydroxamic acids - cycloaddition - rearrangement

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References

1 Beckett RP. Davidson AH. Drummond AH. Huxley P. Wittacker M. Drug Discovery Today 1996, 1: 16

2 Nashino N. Powers JC. J. Biol. Chem. 1980, 255: 3482

3 Fray MJ. Burslem MF. Dickinson RP. Bioorg. Med. Chem. Lett. 2001, 11: 567

4 Fray MJ. Dickinson RP. Bioorg. Med. Chem. Lett. 2001, 11: 571

5 Bergeron RJ. McManis JS. Phanstiel OIV. Vinson JRT. J. Org. Chem. 1995, 60: 109

6 Bergeron RJ. Chem. Rev. 1984, 84: 587

7 Singh S. Chem. Ind. (London) 1994, 452

8 Murahashi Sh.-I. Mitsui H. Shiota T. Tsuda T. Watanabe Sh. J. Org. Chem. 1990, 55: 1736

9 McCaig AE. Meldrum KP. Wightman RH. Tetrahedron 1998, 54: 9429

10 Cicchi S. Höld I. Brandi A. J. Org. Chem. 1993, 58: 5274

11a Mizuno K. Kimura Y. Otsuji Y. Synthesis 1979, 688

11b

The solvent used in place of benzene was Et₂O (yield: 65%)

12 Bayón P. de March P. Figueredo M. Font J. Tetrahedron 1998, 54: 15691

13 Ali SA. Khan JH. Wazeer MIM. Tetrahedron 1988, 44: 5911

14 Ali SA. Wazeer MIM. J. Chem. Soc., Perkin Trans. 1 1988, 597

15 DeShong P. Dicken CM. Staib RR. Freyer AJ. Weinreb SM. J. Org. Chem. 1982, 47: 4397

16 DeShong P. Dicken CM. Leginus JML. Whittle RR. J. Am. Chem. Soc. 1984, 106: 5598

17 Camiletti C. Dhavale DD. Gentilucci L. Trombini C. J. Chem. Soc., Perkin Trans. 1 1993, 3157

18 Meske M. J. Prakt. Chem. 1997, 339: 426

19 Cardona F. Valenza S. Picasso S. Goti A. Brandi A. J. Org. Chem. 1998, 63: 7311

20 Kornblum N. DeLaMare HE. J. Am. Chem. Soc. 1951, 73: 880

21 Defoin A. Sifferlen T. Streith J. Synlett 1997, 1294

22 Defoin A. Brouillard-Poichet A. Streith J. Helv. Chim. Acta 1992, 75: 109

Simple Preparation of N-Benzyl-β-aminohydroxamic Acids by 1,3-Dipolar Cycloaddition­ of Nitrones

Simple Preparation of N-Benzyl-β-aminohydroxamic Acids by 1,3-Dipolar Cycloaddition of Nitrones