The Chemistry of N,N-Bis(siloxy)enamines. Part 8. A General Method for the Preparation of α-Azido Oximes from Aliphatic Nitro Compounds

Alexey Yu Sukhorokov; Igor V. Bliznets; Alexey V. Lesiv; Yulija A. Khomutova; Yuriy A. Strelenko; Sema L. Ioffe

doi:10.1055/s-2005-861836

PAPER

The Chemistry of N,N-Bis(siloxy)enamines. Part 8. [1] A General Method for the Preparation of α-Azido Oximes from Aliphatic Nitro Compounds

Alexey Yu. Sukhorokov, Igor V. Bliznets, Alexey V. Lesiv*, Yulija A. Khomutova, Yuriy A. Strelenko, Sema L. Ioffe*
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Leninsky prosp. 47, Russian Federation
Fax: +7(95)1355328; e-Mail: iof@ioc.ac.ru;

Abstract

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Abstract

A new strategy for the synthesis of α-azido oximes from aliphatic nitro compounds via interaction of N,N-bis(silyloxy)enamines with trimethylsilylazide was realized to give the target products with good yields.

Key words

aliphatic nitro compounds - azidotrimethylsilane - N,N-bis(siloxy)enamines - α-azido oximes

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References

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The derivatives 3 can be purified via rectification in vacuo or after filtration through silica gel. The treatment of thus purified intermediates 3 with methanol gave rise to azido oximes 2 in quantitative yields without any purification.

The attempts to preparate oximes 2 from ANC without isolation of BENA 1 failed.

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