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H. Tavakol and S. Zakery, Multicomponent Additions to C=N Double Bond in Lithium Perchlorate 3rd international conference on Multi-Component Reactions & Related chemistry Amsterdam, the Netherlands 9-13 July 2006, Oral presentation

Abstract:

Multi-component reactions are one of the special types in synthetic organic chemistry, in which three or more starting materials react to give one product [1]. Among these, the Mannich or Mannich-type reactions [2] have been widely used for the synthesis of many Nitrogen-containing molecules such as simple and substituted amines, hydrazines, and oximes [3].

Recently, we focused our researches in synthetic utility of lithium perchlorate/diethyl ether (LPDE) solution (5 M) in the preparation of several nitrogen-containing compounds [4]. We have focused our attention on the use of LPDE medium for activation of C=N double bonds such as imines, iminium salts, hydrazones and oximes versus nucleophilic addition.

One of these multicomponent reactions, is synthesis of  amines, hydrazines, and oximes  in the Mannich-type reductive amination of carbonyl groups [5,6]. The synthesis involves the formation of imines, iminium salts, hydrazones or oximes intermediate followed by in situ reduction. This approach is highly practiced for rapid access to a diverse set of amines due to the wide choice of starting amines and carbonyl compounds. The other reaction is nucleophilic addition to C=N double bond. Via this method, we can add various organomethalic and simple nucleophiles to imines, iminium salts, hydrazones, and oximes for preparation of wide range of Nitrogen-containing compounds.

In summary, multicomponent reactions between carbonyl groups, Nitrogen-containing compounds such as imines, iminium salts, hydrazones, and oximes , and nucleophiles such as various organomethalic nucleophiles or reducing agents, have been successfully carried out by using LPDE solution to afford simple substituted amine and amine derivatives in high yields.

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