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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Published on: February 15, 2016

A concise formal synthesis of alkaloid cryptotackiene and substituted 6H-indolo[2,3-b]quinolines

G S M Sundaram1, C Venkatesh, U K Syam Kumar

  • 1Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India.

The Journal of Organic Chemistry
|August 17, 2004
PubMed

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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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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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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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