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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

Mukund Ghavre1, Jordan Froese1, Milan Pour2

  • 1Chemistry Department and Centre for Biotechnology, Brock University, 1812 Sir Isaac Brock way, St. Catharines, ON, L2S 3A1, Canada.

Angewandte Chemie (International Ed. in English)
|March 13, 2016
PubMed

Keywords:
Amaryllidaceae alkaloidsanticancer drugsbiological activitystructure-activity relationshiptotal synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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