A reliable and easy method for synthesis of nitrogen-containing compounds : Ns-strategy and with high-activity trityl type resin

Abstract

Nitrogen-containing compounds are important chemical entities, many of which show unique bioactivity. In view of this their efficient synthesis is an important issue in the development of pharmaceutically active molecule. However, the handling of highly-polar nitrogen-containing compounds is often problematic, and furthermore the propensity of basic nitrogen compounds to undergo oxidation limits the scope of reaction conditions to which these compounds may be submitted. Accordingly, judicious choice of protecting groups for nitrogen-containing groups is an essential part of the planning of any synthesis involving multiple functionalities. We found that nitrobenzenesulfonyl (Ns) group acts as an active group for the alkylation and succeeded in developing a synthetic procedure involving of the secondary amines by means of this method (Nsstrategy). Furthermore, the Ns group can be removed under mild conditions. Since we presented this method, it has been widely adopted by many chemists and we have also utilized the process in the total synthesis of bioactive natural products. In the course of applying the present methodology to the synthesis of the polyamine toxin, we also succeeded in developing a solid phase procedure using trityl resins with much higher loading values than those typically available commercially. The corresponding solid phase route using this resin represents a significant methodological advance, since no purification steps are required in its execution. In the present articles, we introduce an operationally simple and convenient process for the synthesis of nitrogen-containing compounds based on these methodologies. 2. Synthesis of secondary amines from primary amines

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Cite this paper

@inproceedings{Kan2008ARA, title={A reliable and easy method for synthesis of nitrogen-containing compounds : Ns-strategy and with high-activity trityl type resin}, author={Toshiyuki Kan and Tohru Fukuyama}, year={2008} }