Dissertation
Dissertation > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of aliphatic compounds ( acyclic compounds) > Aliphatic nitrogen-containing compounds > Nitrile,isocyanide and its derivatives > Nitriles

Study on Green Synthetic Method for α-aminonitriles

Author MaYuanHong
Tutor LiZheng
School Northwest Normal University
Course Organic Chemistry
Keywords cyanating reaction potassium hexacyanoferrate(Ⅱ) α-aminonitriles Strecker reaction PEG-400
CLC TQ226.61
Type Master's thesis
Year 2011
Downloads 192
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The organic cyanating reaction is a kind of very important organic reaction, the important organic intermediates such as nitriles, cyanhydrins,α-aminonitriles,α-amino acids,α-hydroxy acids, -keto acids, acyl nitriles and so on may be obtained directly through cyanating reactions. Simultaneously it is also the important way of synthesis of the chiral organic compounds. Therefore the organic cyanating reactions have widespread applications. The reported cyanating reactions usually use hydrocyanic acid, metal cyanides, trimethylsilyl cyanide, cyanoformate, (R2N)2BCN, acetone cyanohydrin, acetyl cyanide as cyaniding reagents. However, these traditional cyanide agents are toxic, corrosive and flammable, therefore the use of these cyanide reagents is extremely unsafe, and will create tremendous pressure to the environment. Therefore searching for, exploring and studying one kind of safe, inexpensive, environmentally friendly cyanide reagent to substitute traditional harmful cyanide reagents has very vital significance. In this paper, an efficient and environmentally friendly method has been developed for the synthesis ofα-aminonitriles via one-pot three-component condensation of carbonyl compounds, amines and potassium hexacyanoferrate(Ⅱ), and the reacting systems of ketones as carbonyl compounds have also been explored in PEG-400 media, which can be called green reactions.The paper is divided into three sections.Section 1This section mainly summarized the application of the different cyanide reagents in organic cyanide reactions and the progress of synthetic methods ofα-aminonitriles. The characters and reactions of traditional cyanide reagents and green cyanide reagents were introduced especially.Section 2An efficient and environmentally friendly method has been developed for the synthesis ofα-aminonitriles via one-pot three-component condensation of aldehydes, amines and potassium hexacyanoferrate(Ⅱ) in the presence of benzoyl chloride as a promoter. This protocol has the features of use of eco-friendly cyanide source, high yield, and simple work-up procedure.Section 3An environmentally friendly method has been explored for the synthesis of -aminonitriles via one-pot three-component condensation of ketones, amines and potassium hexacyanoferrate(Ⅱ) in PEG-400 media. This protocol has the features of use of eco-friendly cyanide source, green reaction medium, high yield, and simple work-up procedure.

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