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Synthesis 2011(9): 1403-1412  
DOI: 10.1055/s-0030-1259995
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A General Procedure for the Synthesis of Unsymmetrically Substituted Tris(β-oximinoalkyl)amines

Artem N. Semakin, Alexey Yu. Sukhorukov*, Sema L. Ioffe*, Vladimir A. Tartakovsky
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
Fax: +7(499)1355328; e-Mail: sukhorukov@server.ioc.ac.ru;
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Publication History

Received 13 January 2011
Publication Date:
07 April 2011 (online)

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Abstract

A first general approach to the synthesis of unsymmetrically substituted tris(β-oximinoalkyl)amines containing two or three different β-oximinoalkyl fragments has been developed. This procedure employs available aliphatic nitro compounds as starting building blocks and their silylation as the key step. This approach provides an efficient strategy for the diversity-oriented synthesis of 1,4,6,10-tetraazaadamantane derivatives.

Key words

amines - ligands - alkylation - cyclization - protecting groups

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4

The only known ‘unsymmetrical’ tris-oxime 1d was described in our recent communication;² however, the method suggested for its preparation is neither general nor efficient.

13

Figure  [³] summarizes the NMR data of products 1a-l as well as the NMR data of the ‘symmetrical’ tris-oximes described in refs. 2 and 6a.